#------------------------------------------------------------------------------
#$Date: 2022-09-02 05:02:30 +0300 (Fri, 02 Sep 2022) $
#$Revision: 277574 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/90/2109067.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2109067
loop_
_publ_author_name
'Ragusa, Arianna C.'
'Peloquin, Andrew J.'
'Shahani, Marjan M.'
'Dowling, Keri N.'
'Golen, James A.'
'McMillen, Colin D.'
'Rabinovich, Daniel'
'Pennington, William T.'
_publ_section_title
;
 Heterocyclic 1,3-diazepine-based thiones and selones as versatile
 halogen-bond acceptors
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520622008150
_journal_volume                  78
_journal_year                    2022
_chemical_formula_moiety         '5(C6 F5 I), 2(C23 H30 N2 Se)'
_chemical_formula_sum            'C76 H60 F25 I5 N4 Se2'
_chemical_formula_weight         2296.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-11-16
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.037(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   25.9292(14)
_cell_length_b                   8.0709(4)
_cell_length_c                   20.4309(11)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.56
_cell_volume                     3934.6(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            61094
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         2.166
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.006
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2204
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.132
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         1.056
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         9058
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0236
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0103P)²+7.6201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0528
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8222
_reflns_number_total             9058
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            rm5061sup1.cif
_cod_data_source_block           2SDiazMesSe_5F5IB
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               2109067
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.692
_shelx_estimated_absorpt_t_min   0.538
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C36-C37 \\sim C37-C38 \\sim C38-C39 \\sim C39-C40 \\sim C40-C41 \\sim C41-C36
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41: within 2A with sigma of
0.003 and sigma for terminal atoms of 0.006 within 2A
4. Others
 Fixed Sof: I3(0.5) F11(0.5) F12(0.5) F13(0.5) F14(0.5) F15(0.5) C36(0.5)
 C37(0.5) C38(0.5) C39(0.5) C40(0.5) C41(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C17(H17), C19(H19)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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 0.36299(2) 0.15544(2) -0.10920(2) 0.02006(4) Uani 1 1 d . . . . .
F1 F 0.48386(7) 0.3203(2) -0.03476(8) 0.0292(3) Uani 1 1 d . . . . .
F2 F 0.56519(7) 0.2949(2) 0.09629(9) 0.0344(4) Uani 1 1 d . . . . .
F3 F 0.55311(6) 0.0830(2) 0.19303(8) 0.0295(3) Uani 1 1 d . . . . .
F4 F 0.46037(6) -0.10999(18) 0.15628(8) 0.0230(3) Uani 1 1 d . . . . .
F5 F 0.37763(6) -0.08396(18) 0.02570(8) 0.0226(3) Uani 1 1 d . . . . .
C24 C 0.42819(10) 0.1194(3) -0.00858(13) 0.0184(5) Uani 1 1 d . . . . .
C25 C 0.47680(11) 0.2123(3) 0.01111(14) 0.0211(5) Uani 1 1 d . . . . .
C26 C 0.51903(10) 0.2011(3) 0.07825(14) 0.0222(5) Uani 1 1 d . . . . .
C27 C 0.51331(10) 0.0921(3) 0.12718(13) 0.0214(5) Uani 1 1 d . . . . .
C28 C 0.46566(10) -0.0048(3) 0.10812(13) 0.0184(5) Uani 1 1 d . . . . .
C29 C 0.42379(10) 0.0099(3) 0.04130(13) 0.0176(5) Uani 1 1 d . . . . .
I2 I 0.82447(2) 0.56411(2) 0.71374(2) 0.02300(4) Uani 1 1 d . . . . .
F6 F 0.84760(7) 0.4894(3) 0.57197(9) 0.0413(5) Uani 1 1 d . . . . .
F7 F 0.93111(9) 0.3325(3) 0.55144(10) 0.0498(5) Uani 1 1 d . . . . .
F8 F 1.01570(8) 0.1920(2) 0.66196(12) 0.0466(5) Uani 1 1 d . . . . .
F9 F 1.01590(8) 0.2089(3) 0.79492(11) 0.0490(5) Uani 1 1 d . . . . .
F10 F 0.93198(8) 0.3638(2) 0.81645(8) 0.0372(4) Uani 1 1 d . . . . .
C30 C 0.88741(10) 0.4339(3) 0.69523(13) 0.0183(5) Uani 1 1 d . . . . .
C31 C 0.88868(11) 0.4229(3) 0.62860(14) 0.0231(5) Uani 1 1 d . . . . .
C32 C 0.93157(12) 0.3434(4) 0.61722(15) 0.0279(6) Uani 1 1 d . . . . .
C33 C 0.97452(11) 0.2720(3) 0.67329(17) 0.0289(6) Uani 1 1 d . . . . .
C34 C 0.97427(11) 0.2807(3) 0.74002(16) 0.0290(6) Uani 1 1 d . . . . .
C35 C 0.93099(11) 0.3605(3) 0.75041(13) 0.0228(5) Uani 1 1 d . . . . .
Se1 Se 0.73177(2) 0.76413(3) 0.26819(2) 0.01628(5) Uani 1 1 d . . . . .
N1 N 0.68680(8) 0.5035(2) 0.31895(11) 0.0167(4) Uani 1 1 d . . . . .
N2 N 0.75425(8) 0.4207(2) 0.27638(11) 0.0175(4) Uani 1 1 d . . . . .
C1 C 0.72370(10) 0.5418(3) 0.28930(12) 0.0154(4) Uani 1 1 d . . . . .
C2 C 0.76653(12) 0.2513(3) 0.30925(16) 0.0284(6) Uani 1 1 d . . . . .
H2A H 0.804787 0.219042 0.314519 0.034 Uiso 1 1 calc R U . . .
H2B H 0.740053 0.171656 0.276056 0.034 Uiso 1 1 calc R U . . .
C3 C 0.76260(13) 0.2353(4) 0.38095(17) 0.0337(7) Uani 1 1 d . . . . .
H3A H 0.780363 0.333056 0.410391 0.040 Uiso 1 1 calc R U . . .
H3B H 0.783566 0.135636 0.405497 0.040 Uiso 1 1 calc R U . . .
C4 C 0.70207(13) 0.2217(4) 0.37435(18) 0.0351(7) Uani 1 1 d . . . . .
H4A H 0.689292 0.105434 0.364189 0.042 Uiso 1 1 calc R U . . .
H4B H 0.699832 0.254260 0.419890 0.042 Uiso 1 1 calc R U . . .
C5 C 0.66415(11) 0.3331(3) 0.31507(15) 0.0250(5) Uani 1 1 d . . . . .
H5A H 0.659108 0.283550 0.268633 0.030 Uiso 1 1 calc R U . . .
H5B H 0.626869 0.339055 0.317692 0.030 Uiso 1 1 calc R U . . .
C6 C 0.78182(10) 0.4493(3) 0.22777(13) 0.0169(5) Uani 1 1 d . . . . .
C7 C 0.83803(10) 0.4949(3) 0.25493(14) 0.0198(5) Uani 1 1 d . . . . .
C8 C 0.86397(11) 0.5146(3) 0.20695(15) 0.0243(5) Uani 1 1 d . . . . .
H8 H 0.902347 0.545733 0.224618 0.029 Uiso 1 1 calc R U . . .
C9 C 0.83560(12) 0.4903(3) 0.13458(15) 0.0249(5) Uani 1 1 d . . . . .
C10 C 0.77979(12) 0.4396(3) 0.10960(14) 0.0250(5) Uani 1 1 d . . . . .
H10 H 0.760162 0.419717 0.060168 0.030 Uiso 1 1 calc R U . . .
C11 C 0.75190(10) 0.4170(3) 0.15534(13) 0.0201(5) Uani 1 1 d . . . . .
C12 C 0.86966(11) 0.5331(4) 0.33263(14) 0.0276(6) Uani 1 1 d . . . . .
H12A H 0.853197 0.630672 0.345544 0.041 Uiso 1 1 calc R U . . .
H12B H 0.909018 0.555278 0.341674 0.041 Uiso 1 1 calc R U . . .
H12C H 0.867327 0.438085 0.361234 0.041 Uiso 1 1 calc R U . . .
C13 C 0.86310(14) 0.5252(4) 0.08306(18) 0.0388(8) Uani 1 1 d . . . . .
H13A H 0.852079 0.635565 0.062308 0.058 Uiso 1 1 calc R U . . .
H13B H 0.851141 0.441861 0.045138 0.058 Uiso 1 1 calc R U . . .
H13C H 0.903922 0.520693 0.108307 0.058 Uiso 1 1 calc R U . . .
C14 C 0.69173(11) 0.3609(4) 0.12740(15) 0.0281(6) Uani 1 1 d . . . . .
H14A H 0.689114 0.256234 0.150231 0.042 Uiso 1 1 calc R U . . .
H14B H 0.678029 0.344715 0.075834 0.042 Uiso 1 1 calc R U . . .
H14C H 0.668887 0.445202 0.137969 0.042 Uiso 1 1 calc R U . . .
C15 C 0.66014(10) 0.6322(3) 0.34395(12) 0.0158(4) Uani 1 1 d . . . . .
C16 C 0.60623(10) 0.6846(3) 0.29970(12) 0.0165(4) Uani 1 1 d . . . . .
C17 C 0.58109(10) 0.8079(3) 0.32509(13) 0.0180(5) Uani 1 1 d . . . . .
H17 H 0.544597 0.845154 0.295628 0.022 Uiso 1 1 calc R U . . .
C18 C 0.60779(10) 0.8777(3) 0.39218(13) 0.0181(5) Uani 1 1 d . . . . .
C19 C 0.66074(10) 0.8197(3) 0.43506(13) 0.0182(5) Uani 1 1 d . . . . .
H19 H 0.678937 0.864592 0.481461 0.022 Uiso 1 1 calc R U . . .
C20 C 0.68807(10) 0.6979(3) 0.41228(12) 0.0170(5) Uani 1 1 d . . . . .
C21 C 0.57537(10) 0.6112(3) 0.22672(13) 0.0226(5) Uani 1 1 d . . . . .
H21A H 0.602250 0.583012 0.205552 0.034 Uiso 1 1 calc R U . . .
H21B H 0.548323 0.692057 0.196465 0.034 Uiso 1 1 calc R U . . .
H21C H 0.555520 0.510925 0.230779 0.034 Uiso 1 1 calc R U . . .
C22 C 0.58091(11) 1.0147(3) 0.41810(15) 0.0248(5) Uani 1 1 d . . . . .
H22A H 0.588977 0.998189 0.468685 0.037 Uiso 1 1 calc R U . . .
H22B H 0.540274 1.012992 0.390963 0.037 Uiso 1 1 calc R U . . .
H22C H 0.596007 1.121794 0.411482 0.037 Uiso 1 1 calc R U . . .
C23 C 0.74582(11) 0.6403(4) 0.46052(14) 0.0259(5) Uani 1 1 d . . . . .
H23A H 0.772019 0.659987 0.437416 0.039 Uiso 1 1 calc R U . . .
H23B H 0.744762 0.521612 0.470074 0.039 Uiso 1 1 calc R U . . .
H23C H 0.758214 0.701816 0.505408 0.039 Uiso 1 1 calc R U . . .
I3 I 1.03484(2) 0.22252(5) 0.98353(2) 0.02758(8) Uani 0.5 1 d . . P A -1
F11 F 0.90480(13) 0.3193(4) 0.92192(16) 0.0248(6) Uani 0.5 1 d . . P A -1
F12 F 0.85170(12) 0.6024(4) 0.92448(16) 0.0269(7) Uani 0.5 1 d . . P A -1
F13 F 0.91056(14) 0.8691(4) 0.99574(17) 0.0314(7) Uani 0.5 1 d . . P A -1
F14 F 1.02388(14) 0.8569(4) 1.05886(16) 0.0308(7) Uani 0.5 1 d . . P A -1
F15 F 1.07926(18) 0.5765(7) 1.0519(3) 0.0298(13) Uani 0.5 1 d . . P A -1
C36 C 0.9939(2) 0.4409(10) 0.9866(4) 0.0174(11) Uani 0.5 1 d D U P A -1
C37 C 0.9359(3) 0.4492(10) 0.9542(6) 0.0181(12) Uani 0.5 1 d D U P A -1
C38 C 0.9076(2) 0.5946(6) 0.9559(2) 0.0194(8) Uani 0.5 1 d D U P A -1
C39 C 0.9368(2) 0.7321(6) 0.9915(3) 0.0178(8) Uani 0.5 1 d D U P A -1
C40 C 0.9957(2) 0.7224(7) 1.0244(3) 0.0221(9) Uani 0.5 1 d D U P A -1
C41 C 1.0237(3) 0.5789(9) 1.0216(4) 0.0179(11) Uani 0.5 1 d D U P A -1
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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C25 C24 I1 120.00(18) . . ?
C25 C24 C29 117.3(2) . . ?
C29 C24 I1 122.61(18) . . ?
F1 C25 C24 120.4(2) . . ?
F1 C25 C26 117.6(2) . . ?
C26 C25 C24 122.0(2) . . ?
F2 C26 C25 120.7(2) . . ?
F2 C26 C27 119.8(2) . . ?
C27 C26 C25 119.4(2) . . ?
F3 C27 C26 120.2(2) . . ?
F3 C27 C28 120.3(2) . . ?
C26 C27 C28 119.5(2) . . ?
F4 C28 C27 119.1(2) . . ?
F4 C28 C29 120.8(2) . . ?
C29 C28 C27 120.1(2) . . ?
F5 C29 C24 120.4(2) . . ?
F5 C29 C28 118.0(2) . . ?
C28 C29 C24 121.6(2) . . ?
C31 C30 I2 122.14(18) . . ?
C31 C30 C35 116.9(2) . . ?
C35 C30 I2 120.96(18) . . ?
F6 C31 C30 120.6(2) . . ?
F6 C31 C32 117.5(2) . . ?
C30 C31 C32 121.9(2) . . ?
F7 C32 C31 120.5(3) . . ?
F7 C32 C33 119.6(2) . . ?
C33 C32 C31 119.9(3) . . ?
F8 C33 C32 119.8(3) . . ?
F8 C33 C34 120.7(3) . . ?
C34 C33 C32 119.4(2) . . ?
F9 C34 C33 119.6(3) . . ?
F9 C34 C35 120.5(3) . . ?
C33 C34 C35 119.9(2) . . ?
F10 C35 C30 120.1(2) . . ?
F10 C35 C34 117.9(2) . . ?
C30 C35 C34 122.0(2) . . ?
C1 N1 C5 121.5(2) . . ?
C1 N1 C15 120.85(19) . . ?
C15 N1 C5 116.73(19) . . ?
C1 N2 C2 127.6(2) . . ?
C1 N2 C6 120.22(19) . . ?
C6 N2 C2 112.09(19) . . ?
N1 C1 Se1 118.93(17) . . ?
N2 C1 Se1 121.44(17) . . ?
N2 C1 N1 119.6(2) . . ?
N2 C2 H2A 108.4 . . ?
N2 C2 H2B 108.4 . . ?
N2 C2 C3 115.4(2) . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C2 C3 C4 112.2(3) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.5(2) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
N1 C5 C4 112.7(2) . . ?
N1 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 N2 119.3(2) . . ?
C7 C6 C11 122.1(2) . . ?
C11 C6 N2 118.4(2) . . ?
C6 C7 C8 117.8(2) . . ?
C6 C7 C12 121.9(2) . . ?
C8 C7 C12 120.2(2) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 C7 122.2(2) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C10 118.3(2) . . ?
C8 C9 C13 121.3(3) . . ?
C10 C9 C13 120.3(3) . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C6 C11 C14 121.3(2) . . ?
C10 C11 C6 117.7(2) . . ?
C10 C11 C14 121.0(2) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N1 118.9(2) . . ?
C16 C15 C20 121.7(2) . . ?
C20 C15 N1 119.4(2) . . ?
C15 C16 C21 121.9(2) . . ?
C17 C16 C15 118.0(2) . . ?
C17 C16 C21 120.2(2) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 122.0(2) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 C22 121.5(2) . . ?
C19 C18 C17 118.2(2) . . ?
C19 C18 C22 120.2(2) . . ?
C18 C19 H19 118.9 . . ?
C18 C19 C20 122.2(2) . . ?
C20 C19 H19 118.9 . . ?
C15 C20 C23 121.9(2) . . ?
C19 C20 C15 117.9(2) . . ?
C19 C20 C23 120.2(2) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C37 C36 I3 120.0(5) . . ?
C41 C36 I3 120.7(4) . . ?
C41 C36 C37 119.3(6) . . ?
F11 C37 C36 122.2(6) . . ?
F11 C37 C38 116.9(5) . . ?
C36 C37 C38 120.9(7) . . ?
F12 C38 C37 120.8(5) . . ?
F12 C38 C39 118.9(4) . . ?
C39 C38 C37 120.3(5) . . ?
F13 C39 C38 121.2(4) . . ?
F13 C39 C40 120.4(4) . . ?
C38 C39 C40 118.4(5) . . ?
F14 C40 C39 118.0(5) . . ?
F14 C40 C41 120.9(5) . . ?
C41 C40 C39 121.1(5) . . ?
F15 C41 C36 120.9(5) . . ?
F15 C41 C40 119.0(5) . . ?
C40 C41 C36 120.0(5) . . ?
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 C24 2.109(2) . ?
F1 C25 1.344(3) . ?
F2 C26 1.340(3) . ?
F3 C27 1.339(3) . ?
F4 C28 1.347(3) . ?
F5 C29 1.345(3) . ?
C24 C25 1.384(3) . ?
C24 C29 1.387(3) . ?
C25 C26 1.383(4) . ?
C26 C27 1.382(4) . ?
C27 C28 1.383(4) . ?
C28 C29 1.377(3) . ?
I2 C30 2.096(2) . ?
F6 C31 1.341(3) . ?
F7 C32 1.342(3) . ?
F8 C33 1.343(3) . ?
F9 C34 1.346(3) . ?
F10 C35 1.340(3) . ?
C30 C31 1.377(3) . ?
C30 C35 1.379(3) . ?
C31 C32 1.380(4) . ?
C32 C33 1.373(4) . ?
C33 C34 1.368(4) . ?
C34 C35 1.381(4) . ?
Se1 C1 1.876(2) . ?
N1 C1 1.353(3) . ?
N1 C5 1.485(3) . ?
N1 C15 1.447(3) . ?
N2 C1 1.348(3) . ?
N2 C2 1.501(3) . ?
N2 C6 1.451(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.513(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.526(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.520(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.391(3) . ?
C6 C11 1.400(3) . ?
C7 C8 1.398(3) . ?
C7 C12 1.506(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(4) . ?
C9 C10 1.394(4) . ?
C9 C13 1.511(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.399(3) . ?
C11 C14 1.506(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.401(3) . ?
C15 C20 1.401(3) . ?
C16 C17 1.396(3) . ?
C16 C21 1.510(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(3) . ?
C18 C19 1.389(3) . ?
C18 C22 1.509(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.394(3) . ?
C20 C23 1.508(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
I3 C36 2.071(8) . ?
F11 C37 1.331(8) . ?
F12 C38 1.337(5) . ?
F13 C39 1.319(6) . ?
F14 C40 1.343(6) . ?
F15 C41 1.327(6) . ?
C36 C37 1.386(6) . ?
C36 C41 1.384(6) . ?
C37 C38 1.392(7) . ?
C38 C39 1.380(5) . ?
C39 C40 1.411(5) . ?
C40 C41 1.379(7) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2A I2 0.99 3.25 3.852(3) 121.0 4_565 yes
C3 H3B F12 0.99 2.54 3.456(4) 154.8 4_565 yes
C5 H5B F4 0.99 2.55 3.530(3) 169.5 2_655 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C24 C25 F1 -3.1(3) . . . . ?
I1 C24 C25 C26 175.48(19) . . . . ?
I1 C24 C29 F5 2.8(3) . . . . ?
I1 C24 C29 C28 -176.29(18) . . . . ?
F1 C25 C26 F2 -0.2(4) . . . . ?
F1 C25 C26 C27 179.7(2) . . . . ?
F2 C26 C27 F3 1.6(4) . . . . ?
F2 C26 C27 C28 -179.7(2) . . . . ?
F3 C27 C28 F4 -1.1(3) . . . . ?
F3 C27 C28 C29 177.3(2) . . . . ?
F4 C28 C29 F5 0.0(3) . . . . ?
F4 C28 C29 C24 179.0(2) . . . . ?
C24 C25 C26 F2 -178.7(2) . . . . ?
C24 C25 C26 C27 1.1(4) . . . . ?
C25 C24 C29 F5 179.9(2) . . . . ?
C25 C24 C29 C28 0.8(4) . . . . ?
C25 C26 C27 F3 -178.2(2) . . . . ?
C25 C26 C27 C28 0.4(4) . . . . ?
C26 C27 C28 F4 -179.7(2) . . . . ?
C26 C27 C28 C29 -1.3(4) . . . . ?
C27 C28 C29 F5 -178.4(2) . . . . ?
C27 C28 C29 C24 0.7(4) . . . . ?
C29 C24 C25 F1 179.8(2) . . . . ?
C29 C24 C25 C26 -1.7(4) . . . . ?
I2 C30 C31 F6 -3.2(4) . . . . ?
I2 C30 C31 C32 177.0(2) . . . . ?
I2 C30 C35 F10 3.7(3) . . . . ?
I2 C30 C35 C34 -177.0(2) . . . . ?
F6 C31 C32 F7 -0.9(4) . . . . ?
F6 C31 C32 C33 -179.5(3) . . . . ?
F7 C32 C33 F8 0.1(4) . . . . ?
F7 C32 C33 C34 -178.8(3) . . . . ?
F8 C33 C34 F9 0.3(4) . . . . ?
F8 C33 C34 C35 -178.7(3) . . . . ?
F9 C34 C35 F10 0.0(4) . . . . ?
F9 C34 C35 C30 -179.3(2) . . . . ?
C30 C31 C32 F7 178.9(3) . . . . ?
C30 C31 C32 C33 0.2(4) . . . . ?
C31 C30 C35 F10 -178.8(2) . . . . ?
C31 C30 C35 C34 0.5(4) . . . . ?
C31 C32 C33 F8 178.8(3) . . . . ?
C31 C32 C33 C34 -0.1(4) . . . . ?
C32 C33 C34 F9 179.1(3) . . . . ?
C32 C33 C34 C35 0.1(4) . . . . ?
C33 C34 C35 F10 179.0(2) . . . . ?
C33 C34 C35 C30 -0.4(4) . . . . ?
C35 C30 C31 F6 179.3(2) . . . . ?
C35 C30 C31 C32 -0.4(4) . . . . ?
N1 C15 C16 C17 179.4(2) . . . . ?
N1 C15 C16 C21 -0.2(3) . . . . ?
N1 C15 C20 C19 -178.9(2) . . . . ?
N1 C15 C20 C23 1.0(3) . . . . ?
N2 C2 C3 C4 78.5(3) . . . . ?
N2 C6 C7 C8 177.3(2) . . . . ?
N2 C6 C7 C12 -6.6(3) . . . . ?
N2 C6 C11 C10 -177.7(2) . . . . ?
N2 C6 C11 C14 2.6(3) . . . . ?
C1 N1 C5 C4 85.7(3) . . . . ?
C1 N1 C15 C16 97.3(3) . . . . ?
C1 N1 C15 C20 -84.4(3) . . . . ?
C1 N2 C2 C3 -23.5(4) . . . . ?
C1 N2 C6 C7 96.7(3) . . . . ?
C1 N2 C6 C11 -88.3(3) . . . . ?
C2 N2 C1 Se1 159.3(2) . . . . ?
C2 N2 C1 N1 -19.9(4) . . . . ?
C2 N2 C6 C7 -81.0(3) . . . . ?
C2 N2 C6 C11 94.0(3) . . . . ?
C2 C3 C4 C5 -37.7(3) . . . . ?
C3 C4 C5 N1 -48.0(3) . . . . ?
C5 N1 C1 Se1 159.24(18) . . . . ?
C5 N1 C1 N2 -21.6(3) . . . . ?
C5 N1 C15 C16 -71.7(3) . . . . ?
C5 N1 C15 C20 106.6(3) . . . . ?
C6 N2 C1 Se1 -18.0(3) . . . . ?
C6 N2 C1 N1 162.8(2) . . . . ?
C6 N2 C2 C3 154.0(2) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C7 C6 C11 C10 -2.9(4) . . . . ?
C7 C6 C11 C14 177.4(2) . . . . ?
C7 C8 C9 C10 -2.0(4) . . . . ?
C7 C8 C9 C13 175.2(2) . . . . ?
C8 C9 C10 C11 1.6(4) . . . . ?
C9 C10 C11 C6 0.8(4) . . . . ?
C9 C10 C11 C14 -179.5(2) . . . . ?
C11 C6 C7 C8 2.5(4) . . . . ?
C11 C6 C7 C12 178.6(2) . . . . ?
C12 C7 C8 C9 -176.2(2) . . . . ?
C13 C9 C10 C11 -175.6(2) . . . . ?
C15 N1 C1 Se1 -9.2(3) . . . . ?
C15 N1 C1 N2 170.0(2) . . . . ?
C15 N1 C5 C4 -105.4(2) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C15 C20 C19 -0.7(3) . . . . ?
C16 C15 C20 C23 179.2(2) . . . . ?
C16 C17 C18 C19 -1.1(3) . . . . ?
C16 C17 C18 C22 178.0(2) . . . . ?
C17 C18 C19 C20 1.6(4) . . . . ?
C18 C19 C20 C15 -0.7(3) . . . . ?
C18 C19 C20 C23 179.3(2) . . . . ?
C20 C15 C16 C17 1.2(3) . . . . ?
C20 C15 C16 C21 -178.5(2) . . . . ?
C21 C16 C17 C18 179.4(2) . . . . ?
C22 C18 C19 C20 -177.5(2) . . . . ?
I3 C36 C37 F11 1.6(12) . . . . ?
I3 C36 C37 C38 179.8(6) . . . . ?
I3 C36 C41 F15 2.2(6) . . . . ?
I3 C36 C41 C40 -178.7(7) . . . . ?
F11 C37 C38 F12 -1.8(11) . . . . ?
F11 C37 C38 C39 176.7(6) . . . . ?
F12 C38 C39 F13 0.9(7) . . . . ?
F12 C38 C39 C40 -179.9(4) . . . . ?
F13 C39 C40 F14 -1.0(7) . . . . ?
F13 C39 C40 C41 178.7(5) . . . . ?
F14 C40 C41 F15 -1.8(10) . . . . ?
F14 C40 C41 C36 179.1(4) . . . . ?
C36 C37 C38 F12 179.9(7) . . . . ?
C36 C37 C38 C39 -1.5(11) . . . . ?
C37 C36 C41 F15 -178.6(10) . . . . ?
C37 C36 C41 C40 0.5(8) . . . . ?
C37 C38 C39 F13 -177.7(6) . . . . ?
C37 C38 C39 C40 1.5(8) . . . . ?
C38 C39 C40 F14 179.9(4) . . . . ?
C38 C39 C40 C41 -0.4(8) . . . . ?
C39 C40 C41 F15 178.5(6) . . . . ?
C39 C40 C41 C36 -0.6(8) . . . . ?
C41 C36 C37 F11 -177.7(6) . . . . ?
C41 C36 C37 C38 0.5(11) . . . . ?

_cod_database_fobs_code 2109067
