#------------------------------------------------------------------------------
#$Date: 2022-10-07 03:49:21 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278411 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567615.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_1567615
loop_
_publ_author_name
'Decato, Daniel A.'
'Sun, Jiyu'
'Boller, Madeleine R.'
'Berryman, Orion B.'
_publ_section_title
;
 Pushing the limits of the hydrogen bond enhanced halogen bond---the case
 of the C--H hydrogen bond
;
_journal_issue                   37
_journal_name_full               'Chemical Science'
_journal_page_first              11156
_journal_page_last               11162
_journal_paper_doi               10.1039/D2SC03792K
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C22 H14 I2 N, C F3 O3 S'
_chemical_formula_sum            'C23 H14 F3 I2 N O3 S'
_chemical_formula_weight         695.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-04-02 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                98.460(2)
_cell_angle_beta                 103.067(2)
_cell_angle_gamma                94.936(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1362(3)
_cell_length_b                   12.3559(6)
_cell_length_c                   14.2656(7)
_cell_measurement_reflns_used    9342
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.622
_cell_measurement_theta_min      2.953
_cell_volume                     1202.63(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_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_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            86479
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_min         2.953
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_type              fine-focus
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.750
_exptl_absorpt_correction_T_max  0.4935
_exptl_absorpt_correction_T_min  0.3601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0747 before and 0.0471 after correction.
The Ratio of minimum to maximum transmission is 0.7297.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.148
_refine_diff_density_min         -1.406
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0275
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0136P)²+5.2915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5332
_reflns_number_total             5965
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03792k2.cif
_cod_data_source_block           umt_ob191
_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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1567609--1567616.cif.
;
_cod_database_code               1567615
_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   0.922
_shelx_estimated_absorpt_t_min   0.609
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.25641(3) 0.18596(2) 0.40948(2) 0.01386(5) Uani 1 1 d . . . . .
I2 I 0.20482(4) 0.47185(2) 0.83851(2) 0.02706(7) Uani 1 1 d . . . . .
N1 N 0.2389(4) 0.7936(2) 0.4647(2) 0.0126(5) Uani 1 1 d . . . . .
C1 C 0.2814(4) 0.2235(3) 0.2741(2) 0.0133(6) Uani 1 1 d . . . . .
C2 C 0.2939(5) 0.1391(3) 0.2009(3) 0.0179(7) Uani 1 1 d . . . . .
H2 H 0.289848 0.065107 0.212152 0.021 Uiso 1 1 calc R U . . .
C3 C 0.3124(5) 0.1629(3) 0.1115(3) 0.0220(7) Uani 1 1 d . . . . .
H3 H 0.321456 0.105045 0.061522 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3180(5) 0.2705(3) 0.0939(2) 0.0215(7) Uani 1 1 d . . . . .
H4 H 0.330561 0.286053 0.032227 0.026 Uiso 1 1 calc R U . . .
C5 C 0.3052(5) 0.3545(3) 0.1661(2) 0.0178(6) Uani 1 1 d . . . . .
H5 H 0.308309 0.428032 0.153758 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2876(4) 0.3330(3) 0.2581(2) 0.0130(6) Uani 1 1 d . . . . .
C7 C 0.2754(5) 0.4227(3) 0.3312(2) 0.0156(6) Uani 1 1 d . . . . .
C8 C 0.2639(5) 0.5013(3) 0.3880(2) 0.0154(6) Uani 1 1 d . . . . .
C9 C 0.2485(5) 0.6012(3) 0.4495(2) 0.0143(6) Uani 1 1 d . . . . .
C10 C 0.2482(4) 0.6977(3) 0.4104(2) 0.0137(6) Uani 1 1 d . . . . .
H10 H 0.254601 0.695376 0.344304 0.016 Uiso 1 1 calc R U . . .
C11 C 0.2365(5) 0.6060(3) 0.5462(3) 0.0166(6) Uani 1 1 d . . . . .
H11 H 0.236179 0.540845 0.574235 0.020 Uiso 1 1 calc R U . . .
C12 C 0.2277(4) 0.8009(3) 0.5581(2) 0.0138(6) Uani 1 1 d . . . . .
H12 H 0.221322 0.870481 0.594967 0.017 Uiso 1 1 calc R U . . .
C13 C 0.2252(4) 0.7067(3) 0.6013(2) 0.0147(6) Uani 1 1 d . . . . .
C14 C 0.2132(5) 0.7165(3) 0.7007(2) 0.0162(6) Uani 1 1 d . . . . .
C15 C 0.2046(5) 0.7182(3) 0.7832(3) 0.0165(6) Uani 1 1 d . . . . .
C16 C 0.1961(5) 0.7208(3) 0.8827(2) 0.0169(6) Uani 1 1 d . . . . .
C17 C 0.1955(5) 0.6243(3) 0.9230(3) 0.0208(7) Uani 1 1 d . . . . .
C18 C 0.1865(6) 0.6295(4) 1.0201(3) 0.0301(9) Uani 1 1 d . . . . .
H18 H 0.187980 0.564281 1.048024 0.036 Uiso 1 1 calc R U . . .
C19 C 0.1756(6) 0.7287(4) 1.0760(3) 0.0337(10) Uani 1 1 d . . . . .
H19 H 0.166821 0.731153 1.141769 0.040 Uiso 1 1 calc R U . . .
C20 C 0.1773(6) 0.8248(4) 1.0367(3) 0.0302(9) Uani 1 1 d . . . . .
H20 H 0.171554 0.893139 1.075715 0.036 Uiso 1 1 calc R U . . .
C21 C 0.1874(5) 0.8212(3) 0.9409(3) 0.0217(7) Uani 1 1 d . . . . .
H21 H 0.188518 0.887191 0.914170 0.026 Uiso 1 1 calc R U . . .
C22 C 0.2492(5) 0.8963(3) 0.4228(3) 0.0173(6) Uani 1 1 d . . . . .
H22A H 0.172370 0.948093 0.451232 0.026 Uiso 1 1 calc R U . . .
H22B H 0.197681 0.878906 0.351800 0.026 Uiso 1 1 calc R U . . .
H22C H 0.384513 0.929697 0.437574 0.026 Uiso 1 1 calc R U . . .
S1 S 0.28790(13) 0.17282(7) 0.68893(6) 0.01875(17) Uani 1 1 d . . . . .
F1 F 0.3169(4) 0.1633(3) 0.87355(17) 0.0443(7) Uani 1 1 d . . . . .
F2 F 0.0855(4) 0.0505(2) 0.77565(19) 0.0392(6) Uani 1 1 d . . . . .
F3 F 0.3794(4) 0.0178(2) 0.7918(2) 0.0490(7) Uani 1 1 d . . . . .
O1 O 0.1503(4) 0.2503(2) 0.6933(2) 0.0304(6) Uani 1 1 d . . . . .
O2 O 0.4873(4) 0.2191(3) 0.7153(2) 0.0325(7) Uani 1 1 d . . . . .
O3 O 0.2341(5) 0.0868(2) 0.6039(2) 0.0316(6) Uani 1 1 d . . . . .
C23 C 0.2659(6) 0.0973(3) 0.7873(3) 0.0237(7) Uani 1 1 d . . . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C12 121.9(3) . . ?
C10 N1 C22 119.5(3) . . ?
C12 N1 C22 118.6(3) . . ?
C2 C1 I1 119.2(2) . . ?
C2 C1 C6 120.5(3) . . ?
C6 C1 I1 120.3(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 C7 122.6(3) . . ?
C5 C6 C7 119.0(3) . . ?
C8 C7 C6 176.2(3) . . ?
C7 C8 C9 175.0(3) . . ?
C10 C9 C8 117.8(3) . . ?
C10 C9 C11 118.9(3) . . ?
C11 C9 C8 123.2(3) . . ?
N1 C10 C9 120.5(3) . . ?
N1 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C9 C11 H11 120.2 . . ?
C13 C11 C9 119.5(3) . . ?
C13 C11 H11 120.2 . . ?
N1 C12 H12 119.9 . . ?
N1 C12 C13 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C13 C12 118.8(3) . . ?
C11 C13 C14 121.9(3) . . ?
C12 C13 C14 119.3(3) . . ?
C15 C14 C13 176.2(4) . . ?
C14 C15 C16 179.5(4) . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 C21 119.3(3) . . ?
C21 C16 C15 119.8(3) . . ?
C16 C17 I2 120.8(3) . . ?
C18 C17 I2 119.7(3) . . ?
C18 C17 C16 119.5(4) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(4) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.5(4) . . ?
C20 C21 H21 119.8 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 S1 O3 114.44(18) . . ?
O1 S1 C23 103.13(18) . . ?
O2 S1 O1 115.67(19) . . ?
O2 S1 O3 115.09(19) . . ?
O2 S1 C23 103.58(18) . . ?
O3 S1 C23 102.37(18) . . ?
F1 C23 S1 111.2(3) . . ?
F1 C23 F2 107.8(3) . . ?
F2 C23 S1 111.7(3) . . ?
F3 C23 S1 111.6(3) . . ?
F3 C23 F1 107.0(3) . . ?
F3 C23 F2 107.3(3) . . ?
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 2.094(3) . ?
I2 C17 2.096(4) . ?
N1 C10 1.332(4) . ?
N1 C12 1.344(4) . ?
N1 C22 1.484(4) . ?
C1 C2 1.388(5) . ?
C1 C6 1.402(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.408(5) . ?
C6 C7 1.428(5) . ?
C7 C8 1.192(5) . ?
C8 C9 1.432(5) . ?
C9 C10 1.389(4) . ?
C9 C11 1.395(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C13 1.389(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.395(4) . ?
C13 C14 1.429(5) . ?
C14 C15 1.189(5) . ?
C15 C16 1.431(5) . ?
C16 C17 1.398(5) . ?
C16 C21 1.402(5) . ?
C17 C18 1.395(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(5) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
S1 O1 1.434(3) . ?
S1 O2 1.431(3) . ?
S1 O3 1.445(3) . ?
S1 C23 1.824(4) . ?
F1 C23 1.328(5) . ?
F2 C23 1.328(5) . ?
F3 C23 1.325(5) . ?
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 C1 C2 C3 -179.3(3) . . . . ?
I1 C1 C6 C5 179.7(2) . . . . ?
I1 C1 C6 C7 -0.7(4) . . . . ?
I2 C17 C18 C19 -178.4(3) . . . . ?
N1 C12 C13 C11 0.6(5) . . . . ?
N1 C12 C13 C14 180.0(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
C2 C1 C6 C7 -179.9(3) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C4 C5 C6 C7 179.8(3) . . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
C8 C9 C10 N1 -178.3(3) . . . . ?
C8 C9 C11 C13 178.9(3) . . . . ?
C9 C11 C13 C12 -0.5(5) . . . . ?
C9 C11 C13 C14 -179.9(3) . . . . ?
C10 N1 C12 C13 0.0(5) . . . . ?
C10 C9 C11 C13 -0.2(5) . . . . ?
C11 C9 C10 N1 0.8(5) . . . . ?
C12 N1 C10 C9 -0.7(5) . . . . ?
C15 C16 C17 I2 -0.5(4) . . . . ?
C15 C16 C17 C18 -179.8(3) . . . . ?
C15 C16 C21 C20 179.4(3) . . . . ?
C16 C17 C18 C19 0.9(6) . . . . ?
C17 C16 C21 C20 -0.4(5) . . . . ?
C17 C18 C19 C20 -1.3(6) . . . . ?
C18 C19 C20 C21 0.9(6) . . . . ?
C19 C20 C21 C16 0.0(6) . . . . ?
C21 C16 C17 I2 179.3(3) . . . . ?
C21 C16 C17 C18 -0.1(5) . . . . ?
C22 N1 C10 C9 176.8(3) . . . . ?
C22 N1 C12 C13 -177.5(3) . . . . ?
O1 S1 C23 F1 -63.1(3) . . . . ?
O1 S1 C23 F2 57.5(3) . . . . ?
O1 S1 C23 F3 177.6(3) . . . . ?
O2 S1 C23 F1 57.9(3) . . . . ?
O2 S1 C23 F2 178.4(3) . . . . ?
O2 S1 C23 F3 -61.5(3) . . . . ?
O3 S1 C23 F1 177.9(3) . . . . ?
O3 S1 C23 F2 -61.6(3) . . . . ?
O3 S1 C23 F3 58.5(3) . . . . ?
