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

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

data_BMS004_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1909801'
loop_
_audit_author_name
_audit_author_address
'Bernd M. Schmidt'
;Heinrich Heine University Dusseldorf
Germany
;
_audit_update_record             
;
2019-04-12 deposited with the CCDC.	2019-05-07 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         'C16 F8 I2 N2, C28 H24 N2, C H Cl3'
_chemical_formula_sum            'C45 H25 Cl3 F8 I2 N4'
_chemical_formula_weight         1133.84

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'
F F 0.0727 0.0534 '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'
I I -0.3257 6.8362 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.2396(7)
_cell_length_b                   12.5466(7)
_cell_length_c                   15.6010(9)
_cell_angle_alpha                104.955(2)
_cell_angle_beta                 101.248(2)
_cell_angle_gamma                102.538(2)
_cell_volume                     2177.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    122(2)
_cell_measurement_reflns_used    9710
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      68.2

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    13.670
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2552
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      122(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            70409
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.801
_diffrn_reflns_theta_max         68.197
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7933
_reflns_number_gt                7459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0540P)²+4.1609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     shelxt
_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         7933
_refine_ls_number_parameters     582
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
N1A N 0.0427(4) 0.9087(4) 0.4011(3) 0.0403(14) Uani 0.789(13) 1 d D U P A 1
N2A N 0.1159(4) 0.9378(4) 0.4756(3) 0.0415(14) Uani 0.789(13) 1 d D U P A 1
N1B N 0.0551(13) 0.9040(15) 0.4636(11) 0.044(5) Uani 0.211(13) 1 d D U P A 2
N2B N 0.1128(12) 0.9336(12) 0.4096(9) 0.033(5) Uani 0.211(13) 1 d D U P A 2
I1 I 0.84282(2) 1.35341(2) 0.57890(2) 0.03101(8) Uani 1 1 d . . . . .
C1 C 0.2264(3) 1.0041(3) 0.4718(4) 0.0499(12) Uani 1 1 d D . . . .
Cl1 Cl 0.23116(12) 0.80244(10) 0.22969(8) 0.0647(3) Uani 1 1 d . . . . .
I2 I -0.65255(2) 0.43431(2) 0.31107(2) 0.03513(9) Uani 1 1 d . . . . .
F2 F 0.1838(2) 1.0467(2) 0.3304(2) 0.0652(8) Uani 1 1 d . . . . .
C2 C 0.2601(3) 1.0564(3) 0.4076(3) 0.0467(11) Uani 1 1 d . . . . .
Cl2 Cl 0.13278(11) 0.56143(10) 0.13055(10) 0.0645(3) Uani 1 1 d . . . . .
Cl3 Cl 0.37341(11) 0.66828(12) 0.15229(8) 0.0603(3) Uani 1 1 d . . . . .
F3 F 0.4014(2) 1.1720(2) 0.36183(18) 0.0524(6) Uani 1 1 d . . . . .
N3 N 0.9280(3) 0.5378(3) 0.3369(2) 0.0343(7) Uani 1 1 d . . . . .
C3 C 0.3729(3) 1.1224(3) 0.4236(3) 0.0391(9) Uani 1 1 d . . . . .
F6 F 0.2862(3) 0.9744(3) 0.6153(2) 0.0660(8) Uani 1 1 d . . . . .
C6 C 0.3119(4) 1.0215(4) 0.5512(4) 0.0483(11) Uani 1 1 d . . . . .
C5 C 0.4239(4) 1.0862(3) 0.5663(3) 0.0428(9) Uani 1 1 d . . . . .
F5 F 0.5015(2) 1.0983(2) 0.64334(18) 0.0564(7) Uani 1 1 d . . . . .
C4 C 0.4580(3) 1.1394(3) 0.5034(3) 0.0343(8) Uani 1 1 d . . . . .
N4 N 1.1265(3) 0.2773(3) 0.2140(3) 0.0416(8) Uani 1 1 d . . . . .
C7 C 0.5745(3) 1.2069(3) 0.5213(3) 0.0357(8) Uani 1 1 d . . . . .
C8 C 0.6729(3) 1.2627(3) 0.5387(2) 0.0317(8) Uani 1 1 d . . . . .
C9 C -0.0630(4) 0.8377(3) 0.4076(4) 0.0496(12) Uani 1 1 d D . . . .
C10 C -0.0899(3) 0.7890(4) 0.4749(3) 0.0509(12) Uani 1 1 d . . . . .
F10 F -0.0113(2) 0.8080(3) 0.55376(19) 0.0751(10) Uani 1 1 d . . . . .
C11 C -0.1989(4) 0.7158(4) 0.4619(3) 0.0448(10) Uani 1 1 d . . . . .
F11 F -0.2190(2) 0.6702(3) 0.52706(18) 0.0653(8) Uani 1 1 d . . . . .
C12 C -0.2877(3) 0.6896(3) 0.3826(3) 0.0361(8) Uani 1 1 d . . . . .
C19 C 0.4104(3) 0.3404(4) 0.0455(3) 0.0381(9) Uani 1 1 d . . . . .
H19 H 0.344355 0.368843 0.040384 0.046 Uiso 1 1 calc R U . . .
C13 C -0.2608(4) 0.7405(3) 0.3160(3) 0.0423(9) Uani 1 1 d . . . . .
F13 F -0.3420(2) 0.7179(3) 0.2379(2) 0.0596(7) Uani 1 1 d . . . . .
C14 C -0.1521(4) 0.8108(4) 0.3284(4) 0.0498(11) Uani 1 1 d . . . . .
F14 F -0.1328(3) 0.8521(3) 0.2594(3) 0.0728(9) Uani 1 1 d . . . . .
C15 C -0.3999(3) 0.6136(3) 0.3678(3) 0.0369(8) Uani 1 1 d . . . . .
C17 C 0.6079(3) 0.3636(3) 0.1278(2) 0.0293(7) Uani 1 1 d . . . . .
C16 C -0.4923(3) 0.5486(3) 0.3520(3) 0.0330(8) Uani 1 1 d . . . . .
C18 C 0.5119(3) 0.4028(3) 0.1192(3) 0.0355(8) Uani 1 1 d . . . . .
H18 H 0.512771 0.472034 0.162577 0.043 Uiso 1 1 calc R U . . .
C20 C 0.4065(3) 0.2412(4) -0.0174(3) 0.0365(8) Uani 1 1 d . . . . .
H20 H 0.337491 0.200440 -0.065315 0.044 Uiso 1 1 calc R U . . .
C21 C 0.5054(3) 0.1975(3) -0.0120(2) 0.0305(7) Uani 1 1 d . . . . .
C22 C 0.6083(3) 0.2600(3) 0.0618(2) 0.0286(7) Uani 1 1 d . . . . .
C23 C 0.5065(3) 0.0971(3) -0.0765(2) 0.0335(8) Uani 1 1 d . . . . .
H23 H 0.438299 0.054777 -0.124844 0.040 Uiso 1 1 calc R U . . .
C24 C 0.6047(3) 0.0575(3) -0.0721(2) 0.0320(8) Uani 1 1 d . . . . .
C25 C 0.7077(3) 0.1204(3) 0.0015(2) 0.0306(7) Uani 1 1 d . . . . .
C26 C 0.7064(3) 0.2205(3) 0.0662(2) 0.0294(7) Uani 1 1 d . . . . .
H26 H 0.774518 0.262719 0.114654 0.035 Uiso 1 1 calc R U . . .
C27 C 0.6063(3) -0.0430(3) -0.1384(3) 0.0398(9) Uani 1 1 d . . . . .
H27 H 0.538906 -0.085003 -0.187649 0.048 Uiso 1 1 calc R U . . .
C28 C 0.7028(4) -0.0799(3) -0.1325(3) 0.0445(10) Uani 1 1 d . . . . .
H28 H 0.702076 -0.148037 -0.177116 0.053 Uiso 1 1 calc R U . . .
C29 C 0.8048(4) -0.0177(3) -0.0603(3) 0.0422(9) Uani 1 1 d . . . . .
H29 H 0.871785 -0.044701 -0.057715 0.051 Uiso 1 1 calc R U . . .
C30 C 0.8091(3) 0.0802(3) 0.0056(3) 0.0327(8) Uani 1 1 d . . . . .
C31 C 0.7169(3) 0.4279(3) 0.2035(2) 0.0284(7) Uani 1 1 d . . . . .
C32 C 0.8012(3) 0.5109(3) 0.1895(2) 0.0307(7) Uani 1 1 d . . . . .
C33 C 0.9046(3) 0.5628(3) 0.2588(3) 0.0320(8) Uani 1 1 d . . . . .
H33 H 0.962290 0.619720 0.249589 0.038 Uiso 1 1 calc R U . . .
C34 C 0.8459(3) 0.4586(4) 0.3491(3) 0.0384(9) Uani 1 1 d . . . . .
H34 H 0.861585 0.440054 0.404689 0.046 Uiso 1 1 calc R U . . .
C35 C 0.7381(3) 0.4008(3) 0.2854(3) 0.0336(8) Uani 1 1 d . . . . .
C36 C 0.7844(4) 0.5445(4) 0.1030(3) 0.0505(11) Uani 1 1 d . . . . .
H36A H 0.760773 0.475288 0.049324 0.076 Uiso 1 1 calc R U . . .
H36B H 0.857499 0.595395 0.103007 0.076 Uiso 1 1 calc R U . . .
H36C H 0.724121 0.584601 0.100478 0.076 Uiso 1 1 calc R U . . .
C37 C 0.6512(4) 0.3123(4) 0.3057(3) 0.0487(11) Uani 1 1 d . . . . .
H37A H 0.573050 0.319129 0.284218 0.073 Uiso 1 1 calc R U . . .
H37B H 0.669456 0.324930 0.372202 0.073 Uiso 1 1 calc R U . . .
H37C H 0.654591 0.235236 0.273951 0.073 Uiso 1 1 calc R U . . .
C38 C 0.9197(3) 0.1472(3) 0.0785(3) 0.0321(8) Uani 1 1 d . . . . .
C39 C 1.0125(3) 0.2096(3) 0.0560(3) 0.0400(9) Uani 1 1 d . . . . .
C40 C 1.1127(3) 0.2732(3) 0.1271(3) 0.0421(10) Uani 1 1 d . . . . .
H40 H 1.175332 0.316707 0.111642 0.051 Uiso 1 1 calc R U . . .
C41 C 1.0389(3) 0.2161(3) 0.2349(3) 0.0419(9) Uani 1 1 d . . . . .
H41 H 1.048100 0.217419 0.297085 0.050 Uiso 1 1 calc R U . . .
C42 C 0.9330(3) 0.1493(3) 0.1704(3) 0.0364(8) Uani 1 1 d . . . . .
C43 C 1.0100(4) 0.2101(5) -0.0405(4) 0.0619(14) Uani 1 1 d . . . . .
H43A H 0.998270 0.131601 -0.079918 0.093 Uiso 1 1 calc R U . . .
H43B H 1.083805 0.259554 -0.040746 0.093 Uiso 1 1 calc R U . . .
H43C H 0.946224 0.239449 -0.063854 0.093 Uiso 1 1 calc R U . . .
C44 C 0.8395(4) 0.0829(4) 0.2015(3) 0.0507(11) Uani 1 1 d . . . . .
H44A H 0.774566 0.116917 0.198239 0.076 Uiso 1 1 calc R U . . .
H44B H 0.870635 0.085525 0.265122 0.076 Uiso 1 1 calc R U . . .
H44C H 0.812329 0.002734 0.161554 0.076 Uiso 1 1 calc R U . . .
C45 C 0.2575(4) 0.6679(4) 0.2028(3) 0.0458(10) Uani 1 1 d . . . . .
H45 H 0.278770 0.649368 0.261409 0.055 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
N1A N2A 1.233(7) . ?
N1A C9 1.441(6) . ?
N2A C1 1.447(6) . ?
N1B N2B 1.275(17) . ?
N1B C9 1.469(15) . ?
N2B C1 1.468(13) . ?
I1 C8 2.027(3) . ?
C1 C6 1.389(7) . ?
C1 C2 1.410(7) . ?
Cl1 C45 1.747(4) . ?
I2 C16 2.032(3) . ?
F2 C2 1.331(5) . ?
C2 C3 1.384(6) . ?
Cl2 C45 1.747(5) . ?
Cl3 C45 1.752(5) . ?
F3 C3 1.336(5) . ?
N3 C33 1.327(5) . ?
N3 C34 1.332(5) . ?
C3 C4 1.393(6) . ?
F6 C6 1.340(6) . ?
C6 C5 1.374(6) . ?
C5 F5 1.330(5) . ?
C5 C4 1.400(6) . ?
C4 C7 1.423(5) . ?
N4 C40 1.319(6) . ?
N4 C41 1.324(6) . ?
C7 C8 1.193(5) . ?
C9 C14 1.389(7) . ?
C9 C10 1.401(7) . ?
C10 F10 1.335(6) . ?
C10 C11 1.390(6) . ?
C11 F11 1.325(5) . ?
C11 C12 1.390(6) . ?
C12 C13 1.406(6) . ?
C12 C15 1.430(5) . ?
C19 C20 1.356(6) . ?
C19 C18 1.427(5) . ?
C19 H19 0.9500 . ?
C13 F13 1.333(5) . ?
C13 C14 1.374(6) . ?
C14 F14 1.349(6) . ?
C15 C16 1.180(5) . ?
C17 C18 1.365(5) . ?
C17 C22 1.436(5) . ?
C17 C31 1.501(5) . ?
C18 H18 0.9500 . ?
C20 C21 1.431(5) . ?
C20 H20 0.9500 . ?
C21 C23 1.399(5) . ?
C21 C22 1.438(5) . ?
C22 C26 1.392(5) . ?
C23 C24 1.393(6) . ?
C23 H23 0.9500 . ?
C24 C27 1.417(6) . ?
C24 C25 1.438(5) . ?
C25 C26 1.399(5) . ?
C25 C30 1.433(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.354(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.419(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.367(6) . ?
C29 H29 0.9500 . ?
C30 C38 1.499(5) . ?
C31 C32 1.391(5) . ?
C31 C35 1.395(5) . ?
C32 C33 1.393(5) . ?
C32 C36 1.504(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.398(5) . ?
C34 H34 0.9500 . ?
C35 C37 1.504(5) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.393(6) . ?
C38 C42 1.403(6) . ?
C39 C40 1.399(6) . ?
C39 C43 1.501(7) . ?
C40 H40 0.9500 . ?
C41 C42 1.407(5) . ?
C41 H41 0.9500 . ?
C42 C44 1.501(6) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45 1.0000 . ?

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
N2A N1A C9 108.3(5) . . ?
N1A N2A C1 110.9(5) . . ?
N2B N1B C9 107.5(12) . . ?
N1B N2B C1 103.6(11) . . ?
C6 C1 C2 116.8(4) . . ?
C6 C1 N2A 110.1(4) . . ?
C2 C1 N2A 132.9(4) . . ?
C6 C1 N2B 147.0(7) . . ?
C2 C1 N2B 94.5(6) . . ?
F2 C2 C3 117.5(5) . . ?
F2 C2 C1 121.2(4) . . ?
C3 C2 C1 121.2(4) . . ?
C33 N3 C34 117.1(3) . . ?
F3 C3 C2 119.7(4) . . ?
F3 C3 C4 118.7(3) . . ?
C2 C3 C4 121.6(4) . . ?
F6 C6 C5 118.2(4) . . ?
F6 C6 C1 120.1(4) . . ?
C5 C6 C1 121.7(4) . . ?
F5 C5 C6 118.4(4) . . ?
F5 C5 C4 119.5(3) . . ?
C6 C5 C4 122.0(4) . . ?
C3 C4 C5 116.7(4) . . ?
C3 C4 C7 122.5(4) . . ?
C5 C4 C7 120.8(4) . . ?
C40 N4 C41 117.2(3) . . ?
C8 C7 C4 178.0(4) . . ?
C7 C8 I1 174.8(3) . . ?
C14 C9 C10 116.2(4) . . ?
C14 C9 N1A 111.0(4) . . ?
C10 C9 N1A 132.7(5) . . ?
C14 C9 N1B 149.6(8) . . ?
C10 C9 N1B 94.0(7) . . ?
F10 C10 C11 116.5(5) . . ?
F10 C10 C9 121.8(4) . . ?
C11 C10 C9 121.7(4) . . ?
F11 C11 C10 119.2(4) . . ?
F11 C11 C12 119.1(4) . . ?
C10 C11 C12 121.7(4) . . ?
C11 C12 C13 116.4(4) . . ?
C11 C12 C15 122.4(4) . . ?
C13 C12 C15 121.2(4) . . ?
C20 C19 C18 121.2(4) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
F13 C13 C14 119.1(4) . . ?
F13 C13 C12 119.3(3) . . ?
C14 C13 C12 121.6(4) . . ?
F14 C14 C13 117.6(5) . . ?
F14 C14 C9 120.0(4) . . ?
C13 C14 C9 122.4(5) . . ?
C16 C15 C12 177.3(4) . . ?
C18 C17 C22 120.3(3) . . ?
C18 C17 C31 121.9(3) . . ?
C22 C17 C31 117.8(3) . . ?
C15 C16 I2 174.1(4) . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C23 C21 C20 122.6(3) . . ?
C23 C21 C22 118.7(3) . . ?
C20 C21 C22 118.7(3) . . ?
C26 C22 C17 121.7(3) . . ?
C26 C22 C21 119.3(3) . . ?
C17 C22 C21 118.9(3) . . ?
C24 C23 C21 122.0(3) . . ?
C24 C23 H23 119.0 . . ?
C21 C23 H23 119.0 . . ?
C23 C24 C27 121.8(3) . . ?
C23 C24 C25 119.3(3) . . ?
C27 C24 C25 118.8(3) . . ?
C26 C25 C30 122.0(3) . . ?
C26 C25 C24 118.7(3) . . ?
C30 C25 C24 119.3(3) . . ?
C22 C26 C25 122.0(3) . . ?
C22 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
C28 C27 C24 120.7(3) . . ?
C28 C27 H27 119.6 . . ?
C24 C27 H27 119.6 . . ?
C27 C28 C29 120.6(4) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C30 C29 C28 121.5(4) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C29 C30 C25 119.0(3) . . ?
C29 C30 C38 120.3(3) . . ?
C25 C30 C38 120.6(3) . . ?
C32 C31 C35 119.6(3) . . ?
C32 C31 C17 119.3(3) . . ?
C35 C31 C17 121.0(3) . . ?
C31 C32 C33 117.6(3) . . ?
C31 C32 C36 122.5(3) . . ?
C33 C32 C36 119.9(3) . . ?
N3 C33 C32 124.3(3) . . ?
N3 C33 H33 117.9 . . ?
C32 C33 H33 117.9 . . ?
N3 C34 C35 124.3(4) . . ?
N3 C34 H34 117.8 . . ?
C35 C34 H34 117.8 . . ?
C31 C35 C34 117.1(3) . . ?
C31 C35 C37 122.7(3) . . ?
C34 C35 C37 120.2(3) . . ?
C32 C36 H36A 109.5 . . ?
C32 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C32 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 C38 C42 118.3(3) . . ?
C39 C38 C30 120.1(4) . . ?
C42 C38 C30 121.6(3) . . ?
C38 C39 C40 117.8(4) . . ?
C38 C39 C43 123.0(4) . . ?
C40 C39 C43 119.2(4) . . ?
N4 C40 C39 124.9(4) . . ?
N4 C40 H40 117.6 . . ?
C39 C40 H40 117.6 . . ?
N4 C41 C42 123.8(4) . . ?
N4 C41 H41 118.1 . . ?
C42 C41 H41 118.1 . . ?
C38 C42 C41 118.0(4) . . ?
C38 C42 C44 122.6(3) . . ?
C41 C42 C44 119.4(4) . . ?
C39 C43 H43A 109.5 . . ?
C39 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C39 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
Cl2 C45 Cl1 110.7(3) . . ?
Cl2 C45 Cl3 110.3(2) . . ?
Cl1 C45 Cl3 111.5(3) . . ?
Cl2 C45 H45 108.1 . . ?
Cl1 C45 H45 108.1 . . ?
Cl3 C45 H45 108.1 . . ?

_refine_diff_density_max         1.519
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.100


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

data_mo_h18_030_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1909802'
loop_
_audit_author_name
_audit_author_address
'Bernd M. Schmidt'
;Heinrich Heine University Dusseldorf
Germany
;
_audit_update_record             
;
2019-04-12 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 N2 O2, C12 F8 I2 N2'
_chemical_formula_sum            'C40 H22 F8 I2 N4 O2'
_chemical_formula_weight         996.42

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2333(5)
_cell_length_b                   13.0502(6)
_cell_length_c                   14.1289(6)
_cell_angle_alpha                98.677(2)
_cell_angle_beta                 99.439(2)
_cell_angle_gamma                97.357(2)
_cell_volume                     1817.29(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9958
_cell_measurement_theta_min      4.586
_cell_measurement_theta_max      54.216

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.129
_exptl_absorpt_coefficient_mu    1.815
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6545
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33960
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.290
_diffrn_reflns_theta_max         27.171
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8053
_reflns_number_gt                7097
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0064P)²+5.3128P] 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         8053
_refine_ls_number_parameters     519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_restrained_S_all      1.220
_refine_ls_shift/su_max          0.003
_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 0.20515(2) 0.77758(2) -0.38498(2) 0.02033(7) Uani 1 1 d . . . . .
O1 O 0.4413(2) 0.07778(19) 0.71108(17) 0.0200(5) Uani 1 1 d . . . . .
N1 N 0.2102(3) 0.5921(2) 0.0054(2) 0.0214(6) Uani 1 1 d . . . . .
C1 C 0.1928(4) 0.7126(3) -0.2584(2) 0.0188(7) Uani 1 1 d . . . . .
F1 F 0.3757(2) 0.62452(17) -0.28125(16) 0.0277(5) Uani 1 1 d . . . . .
O2 O 0.3802(3) -0.15484(19) 0.98747(17) 0.0204(5) Uani 1 1 d . . . . .
N2 N 0.1105(3) 0.5875(2) 0.0468(2) 0.0189(6) Uani 1 1 d . . . . .
C2 C 0.2835(4) 0.6495(3) -0.2276(3) 0.0193(7) Uani 1 1 d . . . . .
F2 F 0.3777(2) 0.55400(18) -0.11411(16) 0.0288(5) Uani 1 1 d . . . . .
F3 F 0.0087(2) 0.72552(18) -0.05946(15) 0.0263(5) Uani 1 1 d . . . . .
N3 N 0.2331(4) 0.3197(3) 0.6103(3) 0.0368(9) Uani 1 1 d . . . . .
C3 C 0.2840(4) 0.6118(3) -0.1418(3) 0.0192(7) Uani 1 1 d . . . . .
F5 F 0.3243(2) 0.46289(17) 0.10601(16) 0.0266(5) Uani 1 1 d . . . . .
C5 C 0.0990(4) 0.6969(3) -0.1137(3) 0.0191(7) Uani 1 1 d . . . . .
F4 F 0.0114(2) 0.79842(18) -0.22390(16) 0.0285(5) Uani 1 1 d . . . . .
N4 N 0.7521(3) 0.1223(3) 0.5387(2) 0.0235(7) Uani 1 1 d . . . . .
C4 C 0.1912(4) 0.6333(3) -0.0826(2) 0.0178(7) Uani 1 1 d . . . . .
F7 F -0.0258(3) 0.5496(2) 0.34468(19) 0.0427(7) Uani 1 1 d . . . . .
C7 C 0.1366(4) 0.5462(3) 0.1350(3) 0.0187(7) Uani 1 1 d . . . . .
F6 F 0.3600(2) 0.41089(19) 0.27941(17) 0.0321(5) Uani 1 1 d . . . . .
C6 C 0.1011(4) 0.7355(3) -0.1992(3) 0.0193(7) Uani 1 1 d . . . . .
C9 C 0.2554(4) 0.4602(3) 0.2542(3) 0.0239(8) Uani 1 1 d . . . . .
F8 F -0.0535(2) 0.61594(18) 0.17463(17) 0.0305(5) Uani 1 1 d . . . . .
C8 C 0.2391(4) 0.4908(3) 0.1642(3) 0.0195(7) Uani 1 1 d . . . . .
C10 C 0.1687(4) 0.4783(3) 0.3178(3) 0.0267(8) Uani 1 1 d . . . . .
C11 C 0.0643(4) 0.5301(3) 0.2875(3) 0.0271(9) Uani 1 1 d . . . . .
C12 C 0.0484(4) 0.5635(3) 0.1989(3) 0.0216(7) Uani 1 1 d . . . . .
C13 C 0.1514(5) 0.2289(4) 0.5948(3) 0.0351(11) Uani 1 1 d . . . . .
H13 H 0.0888 0.2100 0.5351 0.042 Uiso 1 1 calc R U . . .
C15 C 0.2449(3) 0.1883(3) 0.7477(2) 0.0175(7) Uani 1 1 d . . . . .
C14 C 0.1518(4) 0.1590(3) 0.6611(3) 0.0239(8) Uani 1 1 d . . . . .
C16 C 0.3310(4) 0.2839(3) 0.7660(3) 0.0246(8) Uani 1 1 d . . . . .
C17 C 0.3201(5) 0.3456(3) 0.6937(3) 0.0321(10) Uani 1 1 d . . . . .
H17 H 0.3788 0.4106 0.7049 0.039 Uiso 1 1 calc R U . . .
C19 C 0.4307(4) 0.3191(3) 0.8594(3) 0.0319(9) Uani 1 1 d . . . . .
H19A H 0.3833 0.3360 0.9132 0.048 Uiso 1 1 calc R U . . .
H19B H 0.4917 0.3814 0.8542 0.048 Uiso 1 1 calc R U . . .
H19C H 0.4824 0.2627 0.8719 0.048 Uiso 1 1 calc R U . . .
C18 C 0.0579(4) 0.0563(3) 0.6383(3) 0.0311(9) Uani 1 1 d . . . . .
H18A H 0.0030 0.0529 0.6888 0.047 Uiso 1 1 calc R U . . .
H18B H 0.1100 -0.0017 0.6363 0.047 Uiso 1 1 calc R U . . .
H18C H -0.0006 0.0508 0.5748 0.047 Uiso 1 1 calc R U . . .
C20 C 0.2427(3) 0.1191(3) 0.8237(2) 0.0143(6) Uani 1 1 d . . . . .
C21 C 0.3245(3) 0.0420(3) 0.8361(2) 0.0126(6) Uani 1 1 d . . . . .
C22 C 0.3061(3) -0.0222(3) 0.9055(2) 0.0138(6) Uani 1 1 d . . . . .
C23 C 0.2067(4) -0.0101(3) 0.9610(2) 0.0180(7) Uani 1 1 d . . . . .
H23 H 0.1927 -0.0552 1.0065 0.022 Uiso 1 1 calc R U . . .
C24 C 0.1289(4) 0.0672(3) 0.9500(3) 0.0209(7) Uani 1 1 d . . . . .
H24 H 0.0625 0.0765 0.9890 0.025 Uiso 1 1 calc R U . . .
C25 C 0.1473(3) 0.1317(3) 0.8822(3) 0.0186(7) Uani 1 1 d . . . . .
H25 H 0.0936 0.1854 0.8756 0.022 Uiso 1 1 calc R U . . .
C26 C 0.4318(3) 0.0287(3) 0.7768(2) 0.0139(6) Uani 1 1 d . . . . .
C27 C 0.3944(3) -0.1015(3) 0.9245(2) 0.0148(6) Uani 1 1 d . . . . .
C28 C 0.5255(3) -0.0468(3) 0.7991(2) 0.0135(6) Uani 1 1 d . . . . .
C29 C 0.6356(3) -0.0552(3) 0.7514(2) 0.0146(6) Uani 1 1 d . . . . .
C30 C 0.7181(4) -0.1286(3) 0.7731(2) 0.0192(7) Uani 1 1 d . . . . .
H30 H 0.7925 -0.1346 0.7414 0.023 Uiso 1 1 calc R U . . .
C31 C 0.6941(4) -0.1934(3) 0.8400(3) 0.0207(7) Uani 1 1 d . . . . .
H31 H 0.7518 -0.2430 0.8534 0.025 Uiso 1 1 calc R U . . .
C32 C 0.5867(3) -0.1860(3) 0.8869(2) 0.0175(7) Uani 1 1 d . . . . .
H32 H 0.5694 -0.2310 0.9318 0.021 Uiso 1 1 calc R U . . .
C33 C 0.5041(3) -0.1121(3) 0.8678(2) 0.0140(6) Uani 1 1 d . . . . .
C34 C 0.6941(4) 0.0230(3) 0.5142(3) 0.0227(8) Uani 1 1 d . . . . .
H34 H 0.6805 -0.0086 0.4475 0.027 Uiso 1 1 calc R U . . .
C35 C 0.6514(3) -0.0386(3) 0.5794(2) 0.0187(7) Uani 1 1 d . . . . .
C36 C 0.6724(3) 0.0098(3) 0.6771(2) 0.0162(7) Uani 1 1 d . . . . .
C37 C 0.7344(4) 0.1136(3) 0.7052(2) 0.0186(7) Uani 1 1 d . . . . .
C38 C 0.7723(4) 0.1662(3) 0.6326(3) 0.0224(8) Uani 1 1 d . . . . .
H38 H 0.8147 0.2372 0.6510 0.027 Uiso 1 1 calc R U . . .
C39 C 0.7613(4) 0.1701(3) 0.8088(3) 0.0306(9) Uani 1 1 d . . . . .
H39A H 0.8145 0.1310 0.8504 0.046 Uiso 1 1 calc R U . . .
H39B H 0.6760 0.1758 0.8306 0.046 Uiso 1 1 calc R U . . .
H39C H 0.8110 0.2405 0.8130 0.046 Uiso 1 1 calc R U . . .
C40 C 0.5863(4) -0.1507(3) 0.5425(3) 0.0248(8) Uani 1 1 d . . . . .
H40A H 0.5075 -0.1657 0.5723 0.037 Uiso 1 1 calc R U . . .
H40B H 0.6504 -0.1976 0.5598 0.037 Uiso 1 1 calc R U . . .
H40C H 0.5585 -0.1618 0.4715 0.037 Uiso 1 1 calc R U . . .
I2A I 0.2056(4) 0.42644(13) 0.45414(11) 0.0206(3) Uani 0.699(12) 1 d . . P A 1
I2B I 0.1602(9) 0.4058(6) 0.4389(4) 0.0309(8) Uani 0.301(12) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.106(3) . ?
O1 C26 1.214(4) . ?
N1 N2 1.256(4) . ?
N1 C4 1.422(4) . ?
C1 C2 1.378(5) . ?
C1 C6 1.387(5) . ?
F1 C2 1.345(4) . ?
O2 C27 1.224(4) . ?
N2 C7 1.430(4) . ?
C2 C3 1.376(5) . ?
F2 C3 1.338(4) . ?
F3 C5 1.347(4) . ?
N3 C17 1.324(6) . ?
N3 C13 1.327(6) . ?
C3 C4 1.393(5) . ?
F5 C8 1.339(4) . ?
C5 C6 1.379(5) . ?
C5 C4 1.395(5) . ?
F4 C6 1.347(4) . ?
N4 C34 1.324(5) . ?
N4 C38 1.334(5) . ?
F7 C11 1.346(4) . ?
C7 C8 1.391(5) . ?
C7 C12 1.392(5) . ?
F6 C9 1.344(4) . ?
C9 C10 1.378(5) . ?
C9 C8 1.381(5) . ?
F8 C12 1.345(4) . ?
C10 C11 1.379(5) . ?
C10 I2B 2.085(4) . ?
C10 I2A 2.129(4) . ?
C11 C12 1.379(5) . ?
C13 C14 1.402(5) . ?
C13 H13 0.9500 . ?
C15 C14 1.391(5) . ?
C15 C16 1.396(5) . ?
C15 C20 1.504(4) . ?
C14 C18 1.504(6) . ?
C16 C17 1.393(5) . ?
C16 C19 1.500(6) . ?
C17 H17 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 C25 1.389(5) . ?
C20 C21 1.401(4) . ?
C21 C22 1.402(4) . ?
C21 C26 1.499(4) . ?
C22 C23 1.393(4) . ?
C22 C27 1.485(4) . ?
C23 C24 1.374(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C28 1.493(4) . ?
C27 C33 1.491(4) . ?
C28 C33 1.409(4) . ?
C28 C29 1.412(4) . ?
C29 C30 1.391(5) . ?
C29 C36 1.511(4) . ?
C30 C31 1.390(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.379(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.389(5) . ?
C32 H32 0.9500 . ?
C34 C35 1.397(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.398(5) . ?
C35 C40 1.504(5) . ?
C36 C37 1.389(5) . ?
C37 C38 1.396(5) . ?
C37 C39 1.501(5) . ?
C38 H38 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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
N2 N1 C4 114.5(3) . . ?
C2 C1 C6 116.8(3) . . ?
C2 C1 I1 120.2(2) . . ?
C6 C1 I1 122.8(3) . . ?
N1 N2 C7 111.6(3) . . ?
F1 C2 C3 118.3(3) . . ?
F1 C2 C1 120.0(3) . . ?
C3 C2 C1 121.7(3) . . ?
C17 N3 C13 117.7(3) . . ?
F2 C3 C2 118.8(3) . . ?
F2 C3 C4 119.4(3) . . ?
C2 C3 C4 121.8(3) . . ?
F3 C5 C6 118.1(3) . . ?
F3 C5 C4 121.1(3) . . ?
C6 C5 C4 120.8(3) . . ?
C34 N4 C38 117.5(3) . . ?
C3 C4 C5 116.7(3) . . ?
C3 C4 N1 114.3(3) . . ?
C5 C4 N1 128.9(3) . . ?
C8 C7 C12 116.4(3) . . ?
C8 C7 N2 127.8(3) . . ?
C12 C7 N2 115.8(3) . . ?
F4 C6 C5 117.9(3) . . ?
F4 C6 C1 119.9(3) . . ?
C5 C6 C1 122.2(3) . . ?
F6 C9 C10 119.8(3) . . ?
F6 C9 C8 117.9(3) . . ?
C10 C9 C8 122.4(3) . . ?
F5 C8 C9 117.1(3) . . ?
F5 C8 C7 121.9(3) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C10 C11 116.6(3) . . ?
C9 C10 I2B 124.2(3) . . ?
C11 C10 I2B 117.8(3) . . ?
C9 C10 I2A 118.3(3) . . ?
C11 C10 I2A 125.0(3) . . ?
F7 C11 C12 117.9(3) . . ?
F7 C11 C10 120.3(3) . . ?
C12 C11 C10 121.8(3) . . ?
F8 C12 C11 119.0(3) . . ?
F8 C12 C7 119.4(3) . . ?
C11 C12 C7 121.6(3) . . ?
N3 C13 C14 124.1(4) . . ?
N3 C13 H13 118.0 . . ?
C14 C13 H13 118.0 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 C20 118.6(3) . . ?
C16 C15 C20 121.1(3) . . ?
C15 C14 C13 116.8(4) . . ?
C15 C14 C18 121.8(3) . . ?
C13 C14 C18 121.4(4) . . ?
C17 C16 C15 117.0(4) . . ?
C17 C16 C19 121.3(4) . . ?
C15 C16 C19 121.7(3) . . ?
N3 C17 C16 124.3(4) . . ?
N3 C17 H17 117.9 . . ?
C16 C17 H17 117.9 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C25 C20 C21 119.0(3) . . ?
C25 C20 C15 115.8(3) . . ?
C21 C20 C15 125.1(3) . . ?
C20 C21 C22 119.5(3) . . ?
C20 C21 C26 120.5(3) . . ?
C22 C21 C26 120.0(3) . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 C27 118.3(3) . . ?
C21 C22 C27 121.4(3) . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 121.1(3) . . ?
C24 C25 H25 119.4 . . ?
C20 C25 H25 119.4 . . ?
O1 C26 C28 120.7(3) . . ?
O1 C26 C21 120.5(3) . . ?
C28 C26 C21 118.8(3) . . ?
O2 C27 C22 120.8(3) . . ?
O2 C27 C33 120.7(3) . . ?
C22 C27 C33 118.5(3) . . ?
C33 C28 C29 118.9(3) . . ?
C33 C28 C26 120.1(3) . . ?
C29 C28 C26 121.0(3) . . ?
C30 C29 C28 118.7(3) . . ?
C30 C29 C36 116.2(3) . . ?
C28 C29 C36 125.1(3) . . ?
C31 C30 C29 121.5(3) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C32 C31 C30 120.3(3) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C33 119.4(3) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C32 C33 C28 121.2(3) . . ?
C32 C33 C27 117.9(3) . . ?
C28 C33 C27 120.8(3) . . ?
N4 C34 C35 124.7(3) . . ?
N4 C34 H34 117.7 . . ?
C35 C34 H34 117.7 . . ?
C34 C35 C36 116.5(3) . . ?
C34 C35 C40 119.7(3) . . ?
C36 C35 C40 123.8(3) . . ?
C37 C36 C35 120.1(3) . . ?
C37 C36 C29 121.1(3) . . ?
C35 C36 C29 118.6(3) . . ?
C36 C37 C38 117.5(3) . . ?
C36 C37 C39 123.0(3) . . ?
C38 C37 C39 119.5(3) . . ?
N4 C38 C37 123.7(4) . . ?
N4 C38 H38 118.2 . . ?
C37 C38 H38 118.2 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C35 C40 H40A 109.5 . . ?
C35 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C35 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

_refine_diff_density_max         1.087
_refine_diff_density_min         -1.296
_refine_diff_density_rms         0.099







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

data_mo_h18_038_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1909804'
loop_
_audit_author_name
_audit_author_address
'Bernd M. Schmidt'
;Heinrich Heine University Dusseldorf
Germany
;
_audit_update_record             
;
2019-04-12 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H4 F4 I2 N2 '
_chemical_formula_sum            'C12 H4 F4 I2 N2 '
_chemical_formula_weight         505.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.4742 1.8119 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   11.213(2)
_cell_length_b                   4.470(2)
_cell_length_c                   13.278(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.65(3)
_cell_angle_gamma                90
_cell_volume                     664.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5813
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      27.13

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.530
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   0.5608
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    4.772
_shelx_estimated_absorpt_T_min   0.334
_shelx_estimated_absorpt_T_max   0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7433
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         27.104
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1469
_reflns_number_gt                1390
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0160P)²+0.5087P] 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         1469
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0150
_refine_ls_R_factor_gt           0.0136
_refine_ls_wR_factor_ref         0.0335
_refine_ls_wR_factor_gt          0.0329
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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 0.08223(2) 0.10029(3) 0.65951(2) 0.01328(5) Uani 1 1 d . . . . .
F1 F 0.26586(11) 0.7491(3) 0.36639(9) 0.0259(3) Uani 1 1 d . . . . .
C1 C 0.38459(16) 0.7401(4) 0.51902(13) 0.0115(3) Uani 1 1 d . . . . .
N1 N 0.46078(15) 0.9396(4) 0.47109(13) 0.0151(3) Uani 1 1 d . . . . .
F2 F 0.49581(11) 0.6872(3) 0.67582(9) 0.0230(3) Uani 1 1 d . . . . .
C2 C 0.28282(18) 0.6450(4) 0.46095(14) 0.0144(4) Uani 1 1 d . . . . .
C3 C 0.19725(17) 0.4549(4) 0.49624(14) 0.0136(4) Uani 1 1 d . . . . .
H3 H 0.1296 0.3950 0.4544 0.016 Uiso 1 1 calc R U . . .
C6 C 0.39797(17) 0.6210(4) 0.61690(14) 0.0124(4) Uani 1 1 d . . . . .
C5 C 0.31542(17) 0.4330(4) 0.65621(14) 0.0127(4) Uani 1 1 d . . . . .
H5 H 0.3271 0.3583 0.7231 0.015 Uiso 1 1 calc R U . . .
C4 C 0.21428(16) 0.3551(4) 0.59526(14) 0.0106(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 C4 2.0924(19) . ?
F1 C2 1.341(2) . ?
C1 C2 1.402(3) . ?
C1 C6 1.404(3) . ?
C1 N1 1.414(2) . ?
N1 N1 1.253(3) 3_676 ?
F2 C6 1.339(2) . ?
C2 C3 1.385(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C6 C5 1.377(3) . ?
C5 C4 1.395(3) . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 115.44(17) . . ?
C2 C1 N1 115.95(16) . . ?
C6 C1 N1 128.60(17) . . ?
N1 N1 C1 114.6(2) 3_676 . ?
F1 C2 C3 118.00(17) . . ?
F1 C2 C1 118.14(17) . . ?
C3 C2 C1 123.84(17) . . ?
C2 C3 C4 117.40(17) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
F2 C6 C5 117.31(17) . . ?
F2 C6 C1 119.49(17) . . ?
C5 C6 C1 123.19(17) . . ?
C6 C5 C4 118.27(17) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C3 C4 C5 121.77(17) . . ?
C3 C4 I1 120.14(14) . . ?
C5 C4 I1 118.01(14) . . ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.091




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

data_mo_h18_037_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1909803'
loop_
_audit_author_name
_audit_author_address
'Bernd M. Schmidt'
;Heinrich Heine University Dusseldorf
Germany
;
_audit_update_record             
;
2019-04-12 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 N2, C12 F8 I2 N2'
_chemical_formula_sum            'C40 H24 F8 I2 N4'
_chemical_formula_weight         966.43

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'
F F 0.0171 0.0103 '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                   18.7877(13)
_cell_length_b                   7.9384(6)
_cell_length_c                   24.9913(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.538(3)
_cell_angle_gamma                90
_cell_volume                     3652.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9839
_cell_measurement_theta_min      2.698
_cell_measurement_theta_max      27.1545

_exptl_crystal_description       fragment
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             1880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.153
_exptl_absorpt_coefficient_mu    1.799
_shelx_estimated_absorpt_T_min   0.724
_shelx_estimated_absorpt_T_max   0.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6759
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            137004
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.213
_diffrn_reflns_theta_max         27.157
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8092
_reflns_number_gt                7354
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0187P)²+3.4247P] 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         8092
_refine_ls_number_parameters     491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0196
_refine_ls_wR_factor_ref         0.0462
_refine_ls_wR_factor_gt          0.0449
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.003
_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 0.77632(2) 0.46258(2) 0.53646(2) 0.01380(4) Uani 1 1 d . . . . .
F1 F 0.76613(6) 0.06405(14) 0.51532(5) 0.0255(3) Uani 1 1 d . . . . .
C1 C 0.68943(9) 0.3024(2) 0.50433(7) 0.0134(3) Uani 1 1 d . . . . .
N1 N 0.52171(9) -0.0287(2) 0.42910(7) 0.0212(4) Uani 1 1 d . . . . .
I2 I 0.20567(2) -0.44789(2) 0.29826(2) 0.01476(4) Uani 1 1 d . . . . .
F2 F 0.65768(6) -0.13606(14) 0.46785(5) 0.0266(3) Uani 1 1 d . . . . .
C2 C 0.69976(9) 0.1313(2) 0.49784(7) 0.0154(4) Uani 1 1 d . . . . .
N2 N 0.45818(9) 0.0186(2) 0.42445(7) 0.0221(4) Uani 1 1 d . . . . .
F3 F 0.49807(6) 0.33114(14) 0.44571(6) 0.0324(3) Uani 1 1 d . . . . .
C3 C 0.64417(10) 0.0273(2) 0.47368(8) 0.0168(4) Uani 1 1 d . . . . .
N3 N 0.40833(8) 0.8602(2) 0.25620(6) 0.0167(3) Uani 1 1 d . . . . .
F4 F 0.60650(6) 0.52799(14) 0.49131(5) 0.0262(3) Uani 1 1 d . . . . .
C4 C 0.57375(9) 0.0892(2) 0.45554(7) 0.0144(4) Uani 1 1 d . . . . .
F5 F 0.47771(6) -0.34384(13) 0.40983(5) 0.0209(2) Uani 1 1 d . . . . .
C5 C 0.56290(10) 0.2611(2) 0.46301(8) 0.0165(4) Uani 1 1 d . . . . .
C6 C 0.61979(10) 0.3634(2) 0.48654(7) 0.0154(4) Uani 1 1 d . . . . .
F6 F 0.36888(6) -0.53181(13) 0.35942(5) 0.0215(2) Uani 1 1 d . . . . .
C7 C 0.40545(9) -0.0963(2) 0.39712(7) 0.0142(3) Uani 1 1 d . . . . .
F7 F 0.21577(6) -0.05504(14) 0.33137(5) 0.0223(2) Uani 1 1 d . . . . .
F8 F 0.32425(6) 0.13427(14) 0.38395(6) 0.0303(3) Uani 1 1 d . . . . .
C8 C 0.41428(9) -0.2687(2) 0.39040(7) 0.0137(3) Uani 1 1 d . . . . .
C9 C 0.35722(10) -0.3666(2) 0.36429(7) 0.0142(3) Uani 1 1 d . . . . .
N4 N 0.39714(8) 0.8343(2) 0.07279(6) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.28055(9) -0.1285(2) 0.35031(7) 0.0153(4) Uani 1 1 d . . . . .
C10 C 0.28976(9) -0.2990(2) 0.34265(7) 0.0131(3) Uani 1 1 d . . . . .
C13 C 0.40467(10) 0.6925(2) 0.25303(7) 0.0160(4) Uani 1 1 d . . . . .
H13 H 0.3588 0.6426 0.2388 0.019 Uiso 1 1 calc R U . . .
C12 C 0.33633(10) -0.0289(2) 0.37725(8) 0.0180(4) Uani 1 1 d . . . . .
C14 C 0.46385(10) 0.5865(2) 0.26931(7) 0.0142(3) Uani 1 1 d . . . . .
C16 C 0.53650(10) 0.8364(2) 0.29361(7) 0.0144(3) Uani 1 1 d . . . . .
C15 C 0.53198(9) 0.6611(2) 0.28878(7) 0.0118(3) Uani 1 1 d . . . . .
C17 C 0.47285(10) 0.9280(2) 0.27690(8) 0.0169(4) Uani 1 1 d . . . . .
H17 H 0.4755 1.0471 0.2805 0.020 Uiso 1 1 calc R U . . .
C18 C 0.45414(10) 0.3982(2) 0.26611(9) 0.0218(4) Uani 1 1 d . . . . .
H18A H 0.4839 0.3511 0.2417 0.033 Uiso 1 1 calc R U . . .
H18B H 0.4029 0.3715 0.2519 0.033 Uiso 1 1 calc R U . . .
H18C H 0.4693 0.3494 0.3026 0.033 Uiso 1 1 calc R U . . .
C19 C 0.60711(11) 0.9263(2) 0.31452(9) 0.0235(4) Uani 1 1 d . . . . .
H19A H 0.5982 1.0478 0.3158 0.035 Uiso 1 1 calc R U . . .
H19B H 0.6409 0.9040 0.2901 0.035 Uiso 1 1 calc R U . . .
H19C H 0.6282 0.8858 0.3513 0.035 Uiso 1 1 calc R U . . .
C20 C 0.59766(9) 0.5511(2) 0.30015(7) 0.0123(3) Uani 1 1 d . . . . .
C21 C 0.62484(9) 0.4884(2) 0.25421(7) 0.0121(3) Uani 1 1 d . . . . .
C22 C 0.68428(9) 0.3711(2) 0.26327(7) 0.0136(3) Uani 1 1 d . . . . .
C23 C 0.71566(9) 0.3241(2) 0.31809(8) 0.0165(4) Uani 1 1 d . . . . .
H23 H 0.7551 0.2469 0.3248 0.020 Uiso 1 1 calc R U . . .
C24 C 0.68957(10) 0.3889(2) 0.36069(8) 0.0180(4) Uani 1 1 d . . . . .
H24 H 0.7116 0.3577 0.3969 0.022 Uiso 1 1 calc R U . . .
C25 C 0.62987(10) 0.5027(2) 0.35196(8) 0.0163(4) Uani 1 1 d . . . . .
H25 H 0.6122 0.5455 0.3823 0.020 Uiso 1 1 calc R U . . .
C26 C 0.59386(9) 0.5350(2) 0.20064(7) 0.0121(3) Uani 1 1 d . . . . .
H26 H 0.5554 0.6147 0.1947 0.015 Uiso 1 1 calc R U . . .
C27 C 0.61775(9) 0.4680(2) 0.15575(7) 0.0128(3) Uani 1 1 d . . . . .
C28 C 0.67748(9) 0.3515(2) 0.16470(7) 0.0141(3) Uani 1 1 d . . . . .
C29 C 0.70904(9) 0.3064(2) 0.21823(8) 0.0152(4) Uani 1 1 d . . . . .
H29 H 0.7485 0.2294 0.2242 0.018 Uiso 1 1 calc R U . . .
C30 C 0.58317(9) 0.5095(2) 0.10057(7) 0.0144(3) Uani 1 1 d . . . . .
C31 C 0.60899(10) 0.4419(2) 0.05799(8) 0.0182(4) Uani 1 1 d . . . . .
H31 H 0.5862 0.4700 0.0216 0.022 Uiso 1 1 calc R U . . .
C32 C 0.66940(10) 0.3299(2) 0.06704(8) 0.0194(4) Uani 1 1 d . . . . .
H32 H 0.6868 0.2855 0.0368 0.023 Uiso 1 1 calc R U . . .
C33 C 0.70239(10) 0.2858(2) 0.11852(8) 0.0180(4) Uani 1 1 d . . . . .
H33 H 0.7425 0.2105 0.1239 0.022 Uiso 1 1 calc R U . . .
C34 C 0.51849(9) 0.6230(2) 0.09085(7) 0.0131(3) Uani 1 1 d . . . . .
C35 C 0.45008(10) 0.5610(2) 0.09512(7) 0.0150(4) Uani 1 1 d . . . . .
C36 C 0.39184(10) 0.6728(2) 0.08621(7) 0.0174(4) Uani 1 1 d . . . . .
H36 H 0.3456 0.6316 0.0899 0.021 Uiso 1 1 calc R U . . .
C37 C 0.46263(10) 0.8906(2) 0.06869(8) 0.0205(4) Uani 1 1 d . . . . .
H37 H 0.4668 1.0053 0.0588 0.025 Uiso 1 1 calc R U . . .
C38 C 0.52529(10) 0.7931(2) 0.07787(7) 0.0173(4) Uani 1 1 d . . . . .
C39 C 0.43743(11) 0.3784(3) 0.10687(9) 0.0257(4) Uani 1 1 d . . . . .
H39A H 0.4401 0.3104 0.0746 0.039 Uiso 1 1 calc R U . . .
H39B H 0.3893 0.3656 0.1159 0.039 Uiso 1 1 calc R U . . .
H39C H 0.4747 0.3406 0.1378 0.039 Uiso 1 1 calc R U . . .
C40 C 0.59713(11) 0.8706(3) 0.07426(10) 0.0306(5) Uani 1 1 d . . . . .
H40A H 0.5901 0.9896 0.0641 0.046 Uiso 1 1 calc R U . . .
H40B H 0.6178 0.8112 0.0466 0.046 Uiso 1 1 calc R U . . .
H40C H 0.6304 0.8616 0.1097 0.046 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.0983(17) . ?
F1 C2 1.346(2) . ?
C1 C6 1.383(2) . ?
C1 C2 1.386(3) . ?
N1 N2 1.234(2) . ?
N1 C4 1.418(2) . ?
I2 C10 2.1030(17) . ?
F2 C3 1.335(2) . ?
C2 C3 1.373(2) . ?
N2 C7 1.417(2) . ?
F3 C5 1.330(2) . ?
C3 C4 1.399(3) . ?
N3 C17 1.332(2) . ?
N3 C13 1.335(2) . ?
F4 C6 1.340(2) . ?
C4 C5 1.398(3) . ?
F5 C8 1.334(2) . ?
C5 C6 1.377(2) . ?
F6 C9 1.340(2) . ?
C7 C8 1.393(3) . ?
C7 C12 1.400(3) . ?
F7 C11 1.347(2) . ?
F8 C12 1.332(2) . ?
C8 C9 1.378(2) . ?
C9 C10 1.383(2) . ?
N4 C37 1.332(3) . ?
N4 C36 1.334(3) . ?
C11 C12 1.376(3) . ?
C11 C10 1.383(3) . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.406(2) . ?
C14 C18 1.506(2) . ?
C16 C17 1.390(3) . ?
C16 C15 1.398(2) . ?
C16 C19 1.505(2) . ?
C15 C20 1.492(2) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.370(2) . ?
C20 C21 1.436(2) . ?
C21 C26 1.398(2) . ?
C21 C22 1.437(2) . ?
C22 C29 1.399(3) . ?
C22 C23 1.429(2) . ?
C23 C24 1.359(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.423(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.394(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.437(2) . ?
C27 C30 1.440(2) . ?
C28 C29 1.397(3) . ?
C28 C33 1.428(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.365(3) . ?
C30 C34 1.493(2) . ?
C31 C32 1.424(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.357(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C35 1.400(3) . ?
C34 C38 1.401(3) . ?
C35 C36 1.392(2) . ?
C35 C39 1.507(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.389(3) . ?
C37 H37 0.9500 . ?
C38 C40 1.502(3) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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 116.86(16) . . ?
C6 C1 I1 121.61(13) . . ?
C2 C1 I1 121.48(13) . . ?
N2 N1 C4 114.01(16) . . ?
F1 C2 C3 118.54(16) . . ?
F1 C2 C1 119.54(15) . . ?
C3 C2 C1 121.92(16) . . ?
N1 N2 C7 114.79(16) . . ?
F2 C3 C2 119.19(16) . . ?
F2 C3 C4 119.61(16) . . ?
C2 C3 C4 121.20(17) . . ?
C17 N3 C13 117.24(16) . . ?
C5 C4 C3 116.97(16) . . ?
C5 C4 N1 126.96(16) . . ?
C3 C4 N1 116.00(16) . . ?
F3 C5 C6 118.34(16) . . ?
F3 C5 C4 120.87(16) . . ?
C6 C5 C4 120.75(16) . . ?
F4 C6 C5 118.06(16) . . ?
F4 C6 C1 119.65(16) . . ?
C5 C6 C1 122.29(17) . . ?
C8 C7 C12 117.19(16) . . ?
C8 C7 N2 127.00(16) . . ?
C12 C7 N2 115.74(16) . . ?
F5 C8 C9 118.28(16) . . ?
F5 C8 C7 120.98(15) . . ?
C9 C8 C7 120.73(16) . . ?
F6 C9 C8 117.99(16) . . ?
F6 C9 C10 119.86(15) . . ?
C8 C9 C10 122.14(17) . . ?
C37 N4 C36 117.29(16) . . ?
F7 C11 C12 117.98(16) . . ?
F7 C11 C10 120.29(15) . . ?
C12 C11 C10 121.73(16) . . ?
C11 C10 C9 117.11(16) . . ?
C11 C10 I2 121.44(13) . . ?
C9 C10 I2 121.43(13) . . ?
N3 C13 C14 123.92(17) . . ?
N3 C13 H13 118.0 . . ?
C14 C13 H13 118.0 . . ?
F8 C12 C11 119.21(16) . . ?
F8 C12 C7 119.76(16) . . ?
C11 C12 C7 121.03(17) . . ?
C13 C14 C15 117.81(16) . . ?
C13 C14 C18 120.29(16) . . ?
C15 C14 C18 121.90(16) . . ?
C17 C16 C15 117.44(16) . . ?
C17 C16 C19 120.12(17) . . ?
C15 C16 C19 122.43(16) . . ?
C16 C15 C14 118.97(16) . . ?
C16 C15 C20 122.17(16) . . ?
C14 C15 C20 118.74(15) . . ?
N3 C17 C16 124.52(17) . . ?
N3 C17 H17 117.7 . . ?
C16 C17 H17 117.7 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 119.86(16) . . ?
C25 C20 C15 122.45(16) . . ?
C21 C20 C15 117.60(15) . . ?
C26 C21 C20 121.84(16) . . ?
C26 C21 C22 118.92(16) . . ?
C20 C21 C22 119.22(16) . . ?
C29 C22 C23 122.40(16) . . ?
C29 C22 C21 118.96(16) . . ?
C23 C22 C21 118.63(16) . . ?
C24 C23 C22 120.53(16) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 121.13(17) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C20 C25 C24 120.59(17) . . ?
C20 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C27 C26 C21 122.02(16) . . ?
C27 C26 H26 119.0 . . ?
C21 C26 H26 119.0 . . ?
C26 C27 C28 119.16(16) . . ?
C26 C27 C30 121.82(16) . . ?
C28 C27 C30 119.01(16) . . ?
C29 C28 C33 122.36(16) . . ?
C29 C28 C27 118.87(16) . . ?
C33 C28 C27 118.77(16) . . ?
C28 C29 C22 122.04(16) . . ?
C28 C29 H29 119.0 . . ?
C22 C29 H29 119.0 . . ?
C31 C30 C27 119.61(16) . . ?
C31 C30 C34 121.00(16) . . ?
C27 C30 C34 119.38(16) . . ?
C30 C31 C32 121.21(17) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 H31 119.4 . . ?
C33 C32 C31 120.65(17) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C28 120.71(17) . . ?
C32 C33 H33 119.6 . . ?
C28 C33 H33 119.6 . . ?
C35 C34 C38 118.94(16) . . ?
C35 C34 C30 120.37(16) . . ?
C38 C34 C30 120.69(16) . . ?
C36 C35 C34 117.93(17) . . ?
C36 C35 C39 119.65(17) . . ?
C34 C35 C39 122.38(16) . . ?
N4 C36 C35 123.86(17) . . ?
N4 C36 H36 118.1 . . ?
C35 C36 H36 118.1 . . ?
N4 C37 C38 124.43(18) . . ?
N4 C37 H37 117.8 . . ?
C38 C37 H37 117.8 . . ?
C37 C38 C34 117.52(17) . . ?
C37 C38 C40 120.25(18) . . ?
C34 C38 C40 122.22(17) . . ?
C35 C39 H39A 109.5 . . ?
C35 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C35 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.069



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
