#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:12:28 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286050 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/95/1569568.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1569568
loop_
_publ_author_name
'Sun, Jiyu'
'Decato, Daniel A.'
'Bryantsev, Vyacheslav S.'
'John, Eric A.'
'Berryman, Orion B.'
_publ_section_title
;
 The interplay between hydrogen and halogen bonding: substituent effects
 and their role in the hydrogen bond enhanced halogen bond.
;
_journal_issue                   33
_journal_name_full               'Chemical science'
_journal_page_first              8924
_journal_page_last               8935
_journal_paper_doi               10.1039/d3sc02348f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety
'C23 H12 F3 I2 N, C21 H43 N, 1.25(Cl), C6 H12.69 N0.25'
_chemical_formula_sum            'C50 H67.69 Cl1.25 F3 I2 N2.25'
_chemical_formula_weight         1055.37
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.9115(18)
_cell_length_b                   36.9115(18)
_cell_length_c                   8.3724(4)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.982
_cell_measurement_theta_min      2.49
_cell_volume                     11407.1(10)
_computing_cell_refinement       'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            86060
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.468
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.201
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1149 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.7676. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       needle
_exptl_crystal_F_000             4302
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 4004 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.034(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         10071
_refine_ls_number_restraints     92
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0334
_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)+(0.0237P)²+43.3286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                9215
_reflns_number_total             10071
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02348f2.cif
_cod_data_source_block           ob148_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1569562--1569572.cif.
;
_cod_original_cell_volume        11407.0(12)
_cod_database_code               1569568
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H49,H49A,H49B} of C49, All C(H,H) groups
 At 1.5 times of:
  {H41A,H41B,H41C} of C41, {H35A,H35B,H35C} of C35, {H29A,H29B,H29C} of C29,
  {H50D,H50E,H50F} of C50A, {H50A,H50B,H50C} of C50
2. Restrained distances
 N1-H1B = N1-H1A
 0.87 with sigma of 0.02
 F1-C23 \\sim F3A-C23 \\sim F3-C23 \\sim F2A-C23 \\sim F2-C23 \\sim F1A-C23
 with sigma of 0.02
 C50-C49 \\sim C50A-C49
 with sigma of 0.02
3. Restrained planarity
 N1, H1A, H1B, C9, C14
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F1A \\sim F2A \\sim F3A: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 F1, F2, F3, C23, F1A, F2A, F3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C43
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(H49A)=Sof(H49B)=Sof(C50A)=Sof(H50D)=Sof(H50E)=Sof(H50F)=1-FVAR(2)
 Sof(H49)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(H50C)=FVAR(2)
7.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,
 H28B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B),
 C34(H34A,H34B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B),
  C40(H40A,H40B), C42(H42A,H42B), C43(H43A,H43B), C45(H45A,H45B), C46(H46A,
 H46B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C12(H12), C19(H19), C20(H20),
 C21(H21), C22(H22), C49(H49)
7.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C35(H35A,H35B,H35C), C41(H41A,H41B,H41C), C50(H50A,H50B,
 H50C), C50A(H50D,H50E,H50F)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+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 0.70802(2) 0.44272(2) -0.28550(5) 0.03202(11) Uani 1 1 d . . . . .
I2 I 0.84300(2) 0.50867(2) -0.18597(5) 0.02877(10) Uani 1 1 d . . . . .
F1 F 0.6751(5) 0.6895(3) -0.421(3) 0.141(8) Uani 0.61(3) 1 d D U . A 1
F2 F 0.6720(4) 0.6652(3) -0.658(2) 0.123(8) Uani 0.61(3) 1 d D U . A 1
F3 F 0.7180(3) 0.6919(3) -0.5786(19) 0.071(4) Uani 0.61(3) 1 d D U . A 1
N1 N 0.74669(15) 0.53760(14) -0.2833(7) 0.0319(12) Uani 1 1 d D . . . .
H1A H 0.7683(12) 0.534(3) -0.247(8) 0.13(5) Uiso 1 1 d D . . . .
H1B H 0.7340(19) 0.5179(14) -0.278(11) 0.07(3) Uiso 1 1 d D . . . .
N2 N 0.5881(2) 0.78438(17) -0.2777(8) 0.0544(18) Uani 1 1 d . . . . .
C1 C 0.65238(17) 0.44646(16) -0.3408(7) 0.0272(14) Uani 1 1 d . . . . .
C2 C 0.63090(18) 0.41560(17) -0.3329(8) 0.0342(16) Uani 1 1 d . . . . .
H2 H 0.641358 0.393099 -0.302821 0.041 Uiso 1 1 calc R . . . .
C3 C 0.59454(19) 0.41746(19) -0.3686(9) 0.0390(18) Uani 1 1 d . . . . .
H3 H 0.579995 0.396260 -0.363115 0.047 Uiso 1 1 calc R . . . .
C4 C 0.57905(18) 0.45038(19) -0.4126(8) 0.0333(16) Uani 1 1 d . . . . .
H4 H 0.553929 0.451709 -0.436517 0.040 Uiso 1 1 calc R . . . .
C5 C 0.60019(18) 0.48088(19) -0.4214(8) 0.0320(15) Uani 1 1 d . . . . .
H5 H 0.589572 0.503203 -0.452918 0.038 Uiso 1 1 calc R . . . .
C6 C 0.63714(17) 0.47962(17) -0.3845(7) 0.0264(14) Uani 1 1 d . . . . .
C7 C 0.65834(17) 0.51210(17) -0.3925(8) 0.0273(14) Uani 1 1 d . . . . .
C8 C 0.67533(17) 0.53947(18) -0.3975(7) 0.0276(14) Uani 1 1 d . . . . .
C9 C 0.69758(18) 0.57174(17) -0.3991(8) 0.0306(15) Uani 1 1 d . . . . .
C10 C 0.68456(19) 0.60424(18) -0.4570(9) 0.0379(17) Uani 1 1 d . . . . .
H10 H 0.660608 0.605593 -0.498136 0.045 Uiso 1 1 calc R . . . .
C11 C 0.7062(2) 0.63492(19) -0.4556(10) 0.0425(19) Uani 1 1 d . . . . .
C12 C 0.74113(19) 0.63281(18) -0.3972(9) 0.0393(17) Uani 1 1 d . . . . .
H12 H 0.755836 0.653935 -0.398009 0.047 Uiso 1 1 calc R . . . .
C13 C 0.75531(17) 0.60102(17) -0.3378(8) 0.0307(15) Uani 1 1 d . . . . .
C14 C 0.73333(16) 0.56906(16) -0.3370(7) 0.0263(14) Uani 1 1 d . . . . .
C15 C 0.79194(17) 0.59838(15) -0.2870(8) 0.0307(14) Uani 1 1 d . . . . .
C16 C 0.82288(17) 0.59408(15) -0.2455(7) 0.0266(14) Uani 1 1 d . . . . .
C17 C 0.86081(17) 0.58966(15) -0.2041(8) 0.0282(13) Uani 1 1 d . . . . .
C18 C 0.87510(16) 0.55585(16) -0.1729(8) 0.0282(14) Uani 1 1 d . . . . .
C19 C 0.91167(18) 0.55255(19) -0.1372(8) 0.0346(16) Uani 1 1 d . . . . .
H19 H 0.921650 0.529359 -0.115108 0.042 Uiso 1 1 calc R . . . .
C20 C 0.93364(18) 0.5829(2) -0.1337(8) 0.0398(18) Uani 1 1 d . . . . .
H20 H 0.958739 0.580459 -0.110911 0.048 Uiso 1 1 calc R . . . .
C21 C 0.91905(18) 0.61709(19) -0.1635(8) 0.0373(16) Uani 1 1 d . . . . .
H21 H 0.934083 0.637963 -0.159659 0.045 Uiso 1 1 calc R . . . .
C22 C 0.88275(17) 0.62046(16) -0.1985(8) 0.0319(14) Uani 1 1 d . . . . .
H22 H 0.872661 0.643678 -0.218894 0.038 Uiso 1 1 calc R . . . .
C23 C 0.6926(2) 0.6699(2) -0.5229(14) 0.075(3) Uani 1 1 d D U . . .
C24 C 0.5943(3) 0.7514(2) -0.1742(10) 0.057(2) Uani 1 1 d . . . . .
H24A H 0.577743 0.752735 -0.081532 0.069 Uiso 1 1 calc R . . . .
H24B H 0.619405 0.752346 -0.132433 0.069 Uiso 1 1 calc R . . . .
C25 C 0.5888(3) 0.7146(2) -0.2562(9) 0.055(2) Uani 1 1 d . . . . .
H25A H 0.562787 0.711060 -0.279627 0.066 Uiso 1 1 calc R . . . .
H25B H 0.602187 0.714253 -0.358788 0.066 Uiso 1 1 calc R . . . .
C26 C 0.6022(3) 0.6841(2) -0.1509(10) 0.061(2) Uani 1 1 d . . . . .
H26A H 0.588989 0.684826 -0.048028 0.073 Uiso 1 1 calc R . . . .
H26B H 0.628249 0.687818 -0.127971 0.073 Uiso 1 1 calc R . . . .
C27 C 0.5970(2) 0.6469(2) -0.2272(10) 0.054(2) Uani 1 1 d . . . . .
H27A H 0.571085 0.643402 -0.252646 0.065 Uiso 1 1 calc R . . . .
H27B H 0.610800 0.645911 -0.328596 0.065 Uiso 1 1 calc R . . . .
C28 C 0.6096(3) 0.6165(2) -0.1190(12) 0.072(3) Uani 1 1 d . . . . .
H28A H 0.636039 0.618418 -0.100863 0.087 Uiso 1 1 calc R . . . .
H28B H 0.597239 0.618217 -0.014366 0.087 Uiso 1 1 calc R . . . .
C29 C 0.6011(3) 0.5816(3) -0.1949(19) 0.110(4) Uani 1 1 d . . . . .
H29A H 0.613833 0.579821 -0.297274 0.165 Uiso 1 1 calc GR . . . .
H29B H 0.574909 0.579908 -0.213081 0.165 Uiso 1 1 calc GR . . . .
H29C H 0.608828 0.561763 -0.124904 0.165 Uiso 1 1 calc GR . . . .
C30 C 0.5950(2) 0.8172(2) -0.1699(9) 0.0472(19) Uani 1 1 d . . . . .
H30A H 0.577865 0.816141 -0.079008 0.057 Uiso 1 1 calc R . . . .
H30B H 0.619801 0.815303 -0.125820 0.057 Uiso 1 1 calc R . . . .
C31 C 0.5910(2) 0.8536(2) -0.2512(9) 0.052(2) Uani 1 1 d . . . . .
H31A H 0.565733 0.856911 -0.287492 0.063 Uiso 1 1 calc R . . . .
H31B H 0.607061 0.854672 -0.345939 0.063 Uiso 1 1 calc R . . . .
C32 C 0.6012(2) 0.8838(2) -0.1337(9) 0.048(2) Uani 1 1 d . . . . .
H32A H 0.584422 0.883126 -0.041592 0.058 Uiso 1 1 calc R . . . .
H32B H 0.626007 0.879364 -0.092858 0.058 Uiso 1 1 calc R . . . .
C33 C 0.5998(2) 0.92106(19) -0.2086(10) 0.0500(19) Uani 1 1 d . . . . .
H33A H 0.574816 0.925822 -0.245481 0.060 Uiso 1 1 calc R . . . .
H33B H 0.615828 0.921333 -0.303561 0.060 Uiso 1 1 calc R . . . .
C34 C 0.6113(3) 0.9513(2) -0.0967(10) 0.056(2) Uani 1 1 d . . . . .
H34A H 0.636013 0.946168 -0.056522 0.067 Uiso 1 1 calc R . . . .
H34B H 0.594720 0.951788 -0.003818 0.067 Uiso 1 1 calc R . . . .
C35 C 0.6110(3) 0.9883(2) -0.1777(11) 0.068(3) Uani 1 1 d . . . . .
H35A H 0.625901 0.987367 -0.274559 0.102 Uiso 1 1 calc GR . . . .
H35B H 0.620901 1.006477 -0.104408 0.102 Uiso 1 1 calc GR . . . .
H35C H 0.586105 0.994772 -0.206093 0.102 Uiso 1 1 calc GR . . . .
C36 C 0.5498(3) 0.7851(2) -0.3429(9) 0.061(3) Uani 1 1 d . . . . .
H36A H 0.547439 0.806213 -0.414809 0.073 Uiso 1 1 calc R . . . .
H36B H 0.546089 0.763022 -0.408212 0.073 Uiso 1 1 calc R . . . .
C37 C 0.5201(2) 0.7870(3) -0.2202(10) 0.060(2) Uani 1 1 d . . . . .
H37A H 0.521155 0.810494 -0.163739 0.072 Uiso 1 1 calc R . . . .
H37B H 0.523338 0.767393 -0.140555 0.072 Uiso 1 1 calc R . . . .
C38 C 0.4836(3) 0.7828(3) -0.3036(11) 0.074(3) Uani 1 1 d . . . . .
H38A H 0.482036 0.800546 -0.391970 0.089 Uiso 1 1 calc R . . . .
H38B H 0.482005 0.758239 -0.350672 0.089 Uiso 1 1 calc R . . . .
C39 C 0.4518(3) 0.7884(3) -0.1930(13) 0.084(3) Uani 1 1 d . . . . .
H39A H 0.453172 0.813100 -0.147552 0.101 Uiso 1 1 calc R . . . .
H39B H 0.453691 0.770968 -0.103359 0.101 Uiso 1 1 calc R . . . .
C40 C 0.4147(3) 0.7835(3) -0.2748(11) 0.079(3) Uani 1 1 d . . . . .
H40A H 0.413579 0.799506 -0.369511 0.095 Uiso 1 1 calc R . . . .
H40B H 0.412557 0.758179 -0.312644 0.095 Uiso 1 1 calc R . . . .
C41 C 0.3834(3) 0.7917(4) -0.1698(15) 0.108(5) Uani 1 1 d . . . . .
H41A H 0.360814 0.787029 -0.227632 0.162 Uiso 1 1 calc GR . . . .
H41B H 0.384299 0.817219 -0.137631 0.162 Uiso 1 1 calc GR . . . .
H41C H 0.384456 0.776292 -0.074558 0.162 Uiso 1 1 calc GR . . . .
C42 C 0.6125(3) 0.7845(2) -0.4224(11) 0.069(3) Uani 1 1 d . . . . .
H42A H 0.607577 0.806695 -0.485324 0.083 Uiso 1 1 calc R . . . .
H42B H 0.606390 0.763432 -0.490146 0.083 Uiso 1 1 calc R . . . .
C43 C 0.6528(3) 0.7832(3) -0.3833(16) 0.092(4) Uani 1 1 d . U . . .
H43A H 0.658411 0.802720 -0.306062 0.110 Uiso 1 1 calc R . . . .
H43B H 0.658236 0.759787 -0.330938 0.110 Uiso 1 1 calc R . . . .
C44 C 0.6754(6) 0.7871(6) -0.517(2) 0.211(11) Uani 1 1 d . . . . .
F1A F 0.6579(3) 0.6722(5) -0.524(3) 0.083(9) Uani 0.39(3) 1 d D U . A 2
F2A F 0.7050(10) 0.6751(8) -0.664(3) 0.151(15) Uani 0.39(3) 1 d D U . A 2
F3A F 0.7039(9) 0.6978(4) -0.441(4) 0.132(15) Uani 0.39(3) 1 d D U . A 2
Cl1 Cl 0.79136(4) 0.43982(4) -0.2137(2) 0.0361(4) Uani 1 1 d . . . . .
Cl2 Cl 0.500000 0.500000 0.500000 0.0386(8) Uani 1 4 d S T P . .
N3 N 0.500000 0.500000 0.000000 0.038(3) Uani 1 4 d S T P . .
C45 C 0.53316(18) 0.4995(2) 0.1082(8) 0.0366(16) Uani 1 1 d . . . . .
H45A H 0.530381 0.479665 0.186598 0.044 Uiso 1 1 calc R . . . .
H45B H 0.533996 0.522598 0.168544 0.044 Uiso 1 1 calc R . . . .
C46 C 0.5693(2) 0.4946(2) 0.0207(8) 0.0398(17) Uani 1 1 d . . . . .
H46A H 0.571634 0.469139 -0.014796 0.048 Uiso 1 1 calc R . . . .
H46B H 0.569716 0.510280 -0.075271 0.048 Uiso 1 1 calc R . . . .
C47 C 0.60101(19) 0.5043(2) 0.1289(8) 0.0381(17) Uani 1 1 d . . . . .
H47A H 0.598853 0.529987 0.161267 0.046 Uiso 1 1 calc R . . . .
H47B H 0.599743 0.489293 0.226826 0.046 Uiso 1 1 calc R . . . .
C48 C 0.6376(2) 0.4985(3) 0.0497(9) 0.057(2) Uani 1 1 d . . . . .
H48A H 0.640440 0.472405 0.025797 0.068 Uiso 1 1 calc R . . . .
H48B H 0.637834 0.511721 -0.053200 0.068 Uiso 1 1 calc R . . . .
C49 C 0.6696(2) 0.5108(3) 0.1484(12) 0.071(3) Uani 1 1 d D . . . .
H49 H 0.666608 0.511206 0.261121 0.086 Uiso 0.305(18) 1 calc R . . B 1
H49A H 0.664967 0.504936 0.261963 0.086 Uiso 0.695(18) 1 calc R . . B 2
H49B H 0.691359 0.497242 0.114317 0.086 Uiso 0.695(18) 1 calc R . . B 2
C50 C 0.7017(6) 0.5213(8) 0.091(3) 0.050(9) Uani 0.305(18) 1 d D . . B 1
H50A H 0.698014 0.536606 -0.003546 0.076 Uiso 0.305(18) 1 calc GR . . B 1
H50B H 0.715871 0.499871 0.060559 0.076 Uiso 0.305(18) 1 calc GR . . B 1
H50C H 0.714822 0.534998 0.172507 0.076 Uiso 0.305(18) 1 calc GR . . B 1
C50A C 0.6765(4) 0.5478(4) 0.1350(19) 0.073(5) Uani 0.695(18) 1 d D . . B 2
H50D H 0.656036 0.561443 0.179022 0.109 Uiso 0.695(18) 1 calc GR . . B 2
H50E H 0.679726 0.554084 0.022256 0.109 Uiso 0.695(18) 1 calc GR . . B 2
H50F H 0.698564 0.553768 0.194408 0.109 Uiso 0.695(18) 1 calc GR . . B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
C24 N2 C30 105.9(6) . . ?
C24 N2 C36 111.1(7) . . ?
C36 N2 C30 110.7(6) . . ?
C42 N2 C24 111.9(6) . . ?
C42 N2 C30 111.8(7) . . ?
C42 N2 C36 105.5(7) . . ?
C2 C1 I1 119.4(5) . . ?
C2 C1 C6 120.1(6) . . ?
C6 C1 I1 120.5(4) . . ?
C3 C2 C1 120.4(6) . . ?
C2 C3 C4 120.1(6) . . ?
C5 C4 C3 119.8(6) . . ?
C4 C5 C6 121.0(7) . . ?
C1 C6 C5 118.7(6) . . ?
C1 C6 C7 121.7(6) . . ?
C5 C6 C7 119.6(6) . . ?
C8 C7 C6 178.6(7) . . ?
C7 C8 C9 176.9(7) . . ?
C10 C9 C8 121.4(6) . . ?
C10 C9 C14 120.8(6) . . ?
C14 C9 C8 117.8(6) . . ?
C9 C10 C11 120.4(7) . . ?
C10 C11 C23 120.6(7) . . ?
C12 C11 C10 119.7(7) . . ?
C12 C11 C23 119.7(6) . . ?
C13 C12 C11 122.0(6) . . ?
C12 C13 C14 119.2(6) . . ?
C12 C13 C15 121.9(6) . . ?
C15 C13 C14 118.8(6) . . ?
N1 C14 C9 121.6(5) . . ?
N1 C14 C13 120.5(6) . . ?
C9 C14 C13 117.8(6) . . ?
C16 C15 C13 176.3(6) . . ?
C15 C16 C17 176.9(7) . . ?
C18 C17 C16 121.0(5) . . ?
C18 C17 C22 120.5(6) . . ?
C22 C17 C16 118.4(5) . . ?
C17 C18 I2 121.5(5) . . ?
C17 C18 C19 119.5(6) . . ?
C19 C18 I2 119.0(5) . . ?
C20 C19 C18 120.2(7) . . ?
C19 C20 C21 120.2(6) . . ?
C22 C21 C20 119.7(6) . . ?
C21 C22 C17 119.9(6) . . ?
F1 C23 F2 109.6(13) . . ?
F1 C23 F3 104.1(10) . . ?
F1 C23 C11 113.7(11) . . ?
F2 C23 C11 112.8(8) . . ?
F3 C23 F2 100.4(11) . . ?
F3 C23 C11 115.1(8) . . ?
F1A C23 C11 113.3(10) . . ?
F1A C23 F3A 105.6(18) . . ?
F2A C23 C11 111.0(13) . . ?
F2A C23 F1A 109.8(19) . . ?
F2A C23 F3A 105(2) . . ?
F3A C23 C11 112.0(11) . . ?
N2 C24 C25 115.9(7) . . ?
C26 C25 C24 110.7(7) . . ?
C25 C26 C27 112.6(7) . . ?
C28 C27 C26 112.2(7) . . ?
C29 C28 C27 109.0(9) . . ?
C31 C30 N2 114.9(6) . . ?
C30 C31 C32 109.5(6) . . ?
C33 C32 C31 112.7(6) . . ?
C32 C33 C34 113.7(7) . . ?
C33 C34 C35 112.5(7) . . ?
C37 C36 N2 115.8(6) . . ?
C36 C37 C38 109.1(7) . . ?
C39 C38 C37 113.1(7) . . ?
C38 C39 C40 113.7(8) . . ?
C41 C40 C39 113.9(8) . . ?
N2 C42 C43 114.2(8) . . ?
C44 C43 C42 114.0(16) . . ?
C45 N3 C45 107.0(5) 3_565 4_655 ?
C45 N3 C45 110.7(3) 3_565 2_665 ?
C45 N3 C45 110.7(3) 4_655 2_665 ?
C45 N3 C45 110.7(3) 3_565 . ?
C45 N3 C45 110.7(3) 4_655 . ?
C45 N3 C45 107.0(5) 2_665 . ?
N3 C45 C46 114.6(5) . . ?
C47 C46 C45 110.9(6) . . ?
C48 C47 C46 113.0(6) . . ?
C49 C48 C47 114.4(7) . . ?
C50 C49 C48 125.6(15) . . ?
C50A C49 C48 113.2(10) . . ?
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 2.110(6) . ?
I2 C18 2.109(6) . ?
F1 C23 1.295(14) . ?
F2 C23 1.371(14) . ?
F3 C23 1.325(12) . ?
N1 C14 1.340(8) . ?
N2 C24 1.512(9) . ?
N2 C30 1.530(10) . ?
N2 C36 1.517(11) . ?
N2 C42 1.509(11) . ?
C1 C2 1.389(9) . ?
C1 C6 1.396(9) . ?
C2 C3 1.377(10) . ?
C3 C4 1.393(10) . ?
C4 C5 1.372(9) . ?
C5 C6 1.399(9) . ?
C6 C7 1.433(9) . ?
C7 C8 1.190(9) . ?
C8 C9 1.447(9) . ?
C9 C10 1.380(10) . ?
C9 C14 1.422(9) . ?
C10 C11 1.386(10) . ?
C11 C12 1.381(10) . ?
C11 C23 1.495(12) . ?
C12 C13 1.378(9) . ?
C13 C14 1.432(8) . ?
C13 C15 1.421(9) . ?
C15 C16 1.204(8) . ?
C16 C17 1.452(9) . ?
C17 C18 1.380(8) . ?
C17 C22 1.397(8) . ?
C18 C19 1.388(9) . ?
C19 C20 1.384(10) . ?
C20 C21 1.394(10) . ?
C21 C22 1.377(9) . ?
C23 F1A 1.285(14) . ?
C23 F2A 1.284(18) . ?
C23 F3A 1.305(16) . ?
C24 C25 1.534(11) . ?
C25 C26 1.513(11) . ?
C26 C27 1.526(11) . ?
C27 C28 1.515(12) . ?
C28 C29 1.471(15) . ?
C30 C31 1.514(10) . ?
C31 C32 1.535(11) . ?
C32 C33 1.511(10) . ?
C33 C34 1.516(11) . ?
C34 C35 1.525(11) . ?
C36 C37 1.503(12) . ?
C37 C38 1.528(12) . ?
C38 C39 1.508(14) . ?
C39 C40 1.543(12) . ?
C40 C41 1.482(15) . ?
C42 C43 1.523(16) . ?
C43 C44 1.401(17) . ?
N3 C45 1.523(7) 3_565 ?
N3 C45 1.523(7) 4_655 ?
N3 C45 1.523(7) 2_665 ?
N3 C45 1.523(7) . ?
C45 C46 1.532(10) . ?
C46 C47 1.524(10) . ?
C47 C48 1.519(11) . ?
C48 C49 1.512(11) . ?
C49 C50 1.34(2) . ?
C49 C50A 1.391(15) . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 0.366 208 41 ' '
2 0.250 0.750 0.538 413 83 ' '
3 0.250 0.250 0.657 412 83 ' '
4 0.500 1.000 0.522 208 41 ' '
5 0.750 0.250 0.038 413 83 ' '
6 0.750 0.750 0.157 412 83 ' '
