#------------------------------------------------------------------------------
#$Date: 2022-10-07 03:49:21 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278411 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567611.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_1567611
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             2020-06-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-02 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                74.307(2)
_cell_angle_beta                 71.324(2)
_cell_angle_gamma                79.269(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5783(4)
_cell_length_b                   11.1636(6)
_cell_length_c                   13.3063(7)
_cell_measurement_reflns_used    9051
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.715
_cell_measurement_theta_min      2.804
_cell_volume                     1155.23(10)
_computing_cell_refinement       'SAINT V8.38A (BRUKER, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER, 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      100.0
_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 0.999
_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  0.0493
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36937
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.759
_diffrn_reflns_theta_min         2.521
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.863
_exptl_absorpt_correction_T_max  0.6037
_exptl_absorpt_correction_T_min  0.4467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0746 before and 0.0561 after correction. The Ratio of minimum to maximum transmission is 0.7399. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_description       rod
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.996
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0276
_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)+(0.0126P)²+1.9348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0474
_refine_ls_wR_factor_ref         0.0517
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4802
_reflns_number_total             5990
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03792k2.cif
_cod_data_source_block           umt_ob149
_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               1567611
_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   0.894
_shelx_estimated_absorpt_t_min   0.283
_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), C10(H10), C11(H11), C12(H12), C13(H13), 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 0.90176(2) 0.26869(2) 0.42900(2) 0.01437(5) Uani 1 1 d . . . . .
I2 I 0.29462(2) 0.50110(2) 0.80800(2) 0.01591(5) Uani 1 1 d . . . . .
S1 S 0.54082(9) 0.20019(7) 0.70616(6) 0.01737(15) Uani 1 1 d . . . . .
F1 F 0.7078(2) 0.06187(17) 0.84038(16) 0.0281(4) Uani 1 1 d . . . . .
F2 F 0.5737(2) 0.23043(17) 0.88750(14) 0.0253(4) Uani 1 1 d . . . . .
F3 F 0.4432(2) 0.07419(18) 0.90893(14) 0.0293(4) Uani 1 1 d . . . . .
O1 O 0.6711(3) 0.2799(2) 0.65231(18) 0.0329(6) Uani 1 1 d . . . . .
O2 O 0.3758(3) 0.2649(2) 0.72855(18) 0.0266(5) Uani 1 1 d . . . . .
O3 O 0.5576(3) 0.0894(2) 0.66629(18) 0.0310(6) Uani 1 1 d . . . . .
N1 N 0.7520(3) 0.7090(2) 0.46853(18) 0.0118(5) Uani 1 1 d . . . . .
C1 C 0.8817(3) 0.7260(3) 0.3760(2) 0.0141(6) Uani 1 1 d . . . . .
C2 C 0.9301(4) 0.8453(3) 0.3272(2) 0.0161(6) Uani 1 1 d . . . . .
H2 H 1.017324 0.858226 0.261208 0.019 Uiso 1 1 calc R . . . .
C3 C 0.8524(4) 0.9451(3) 0.3738(2) 0.0158(6) Uani 1 1 d . . . . .
H3 H 0.885356 1.026571 0.340231 0.019 Uiso 1 1 calc R . . . .
C4 C 0.7253(3) 0.9248(3) 0.4704(2) 0.0149(6) Uani 1 1 d . . . . .
H4 H 0.673039 0.992093 0.504684 0.018 Uiso 1 1 calc R . . . .
C5 C 0.6748(3) 0.8061(3) 0.5168(2) 0.0127(5) Uani 1 1 d . . . . .
C6 C 0.9652(3) 0.6208(3) 0.3325(2) 0.0140(6) Uani 1 1 d . . . . .
C7 C 1.0426(3) 0.5350(3) 0.2938(2) 0.0133(6) Uani 1 1 d . . . . .
C8 C 1.1341(3) 0.4350(3) 0.2435(2) 0.0132(6) Uani 1 1 d . . . . .
C9 C 1.0928(3) 0.3109(3) 0.2845(2) 0.0135(6) Uani 1 1 d . . . . .
C10 C 1.1824(4) 0.2172(3) 0.2325(2) 0.0176(6) Uani 1 1 d . . . . .
H10 H 1.155590 0.133525 0.261226 0.021 Uiso 1 1 calc R . . . .
C11 C 1.3115(4) 0.2456(3) 0.1383(2) 0.0197(6) Uani 1 1 d . . . . .
H11 H 1.370642 0.181627 0.101374 0.024 Uiso 1 1 calc R . . . .
C12 C 1.3547(4) 0.3667(3) 0.0977(2) 0.0183(6) Uani 1 1 d . . . . .
H12 H 1.444426 0.385122 0.033828 0.022 Uiso 1 1 calc R . . . .
C13 C 1.2682(3) 0.4604(3) 0.1494(2) 0.0150(6) Uani 1 1 d . . . . .
H13 H 1.299416 0.542978 0.121388 0.018 Uiso 1 1 calc R . . . .
C14 C 0.5447(3) 0.7836(3) 0.6157(2) 0.0146(6) Uani 1 1 d . . . . .
C15 C 0.4378(4) 0.7746(3) 0.7006(2) 0.0150(6) Uani 1 1 d . . . . .
C16 C 0.3113(3) 0.7734(3) 0.8020(2) 0.0140(6) Uani 1 1 d . . . . .
C17 C 0.2288(3) 0.6682(3) 0.8615(2) 0.0151(6) Uani 1 1 d . . . . .
C18 C 0.1055(4) 0.6740(3) 0.9582(2) 0.0202(6) Uani 1 1 d . . . . .
H18 H 0.045787 0.603969 0.997113 0.024 Uiso 1 1 calc R . . . .
C19 C 0.0689(4) 0.7815(3) 0.9985(3) 0.0241(7) Uani 1 1 d . . . . .
H19 H -0.015416 0.784659 1.064829 0.029 Uiso 1 1 calc R . . . .
C20 C 0.1553(4) 0.8844(3) 0.9421(3) 0.0231(7) Uani 1 1 d . . . . .
H20 H 0.132390 0.956979 0.970921 0.028 Uiso 1 1 calc R . . . .
C21 C 0.2747(4) 0.8812(3) 0.8439(2) 0.0175(6) Uani 1 1 d . . . . .
H21 H 0.332153 0.952339 0.804609 0.021 Uiso 1 1 calc R . . . .
C22 C 0.6950(4) 0.5821(3) 0.5161(2) 0.0169(6) Uani 1 1 d . . . . .
H22A H 0.781599 0.524270 0.542765 0.025 Uiso 1 1 calc GR . . . .
H22B H 0.671991 0.552085 0.460049 0.025 Uiso 1 1 calc GR . . . .
H22C H 0.594064 0.586370 0.576617 0.025 Uiso 1 1 calc GR . . . .
C23 C 0.5678(4) 0.1388(3) 0.8422(2) 0.0164(6) 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
O1 S1 O2 114.93(15) . . ?
O1 S1 O3 115.93(15) . . ?
O1 S1 C23 102.97(14) . . ?
O2 S1 C23 102.53(13) . . ?
O3 S1 O2 114.42(14) . . ?
O3 S1 C23 103.50(13) . . ?
C1 N1 C22 118.8(2) . . ?
C5 N1 C1 120.9(2) . . ?
C5 N1 C22 120.3(2) . . ?
N1 C1 C2 119.5(2) . . ?
N1 C1 C6 119.0(2) . . ?
C2 C1 C6 121.5(3) . . ?
C3 C2 C1 120.5(3) . . ?
C2 C3 C4 119.1(3) . . ?
C5 C4 C3 119.9(3) . . ?
N1 C5 C4 120.0(3) . . ?
N1 C5 C14 119.3(2) . . ?
C4 C5 C14 120.7(3) . . ?
C7 C6 C1 176.7(3) . . ?
C6 C7 C8 177.7(3) . . ?
C9 C8 C7 122.1(3) . . ?
C13 C8 C7 119.5(3) . . ?
C13 C8 C9 118.4(3) . . ?
C8 C9 I1 119.2(2) . . ?
C10 C9 I1 120.4(2) . . ?
C10 C9 C8 120.4(3) . . ?
C9 C10 C11 120.0(3) . . ?
C12 C11 C10 120.3(3) . . ?
C13 C12 C11 120.3(3) . . ?
C12 C13 C8 120.6(3) . . ?
C15 C14 C5 173.9(3) . . ?
C14 C15 C16 175.7(3) . . ?
C17 C16 C15 122.6(3) . . ?
C17 C16 C21 119.5(3) . . ?
C21 C16 C15 117.9(3) . . ?
C16 C17 I2 120.4(2) . . ?
C18 C17 I2 119.9(2) . . ?
C18 C17 C16 119.7(3) . . ?
C19 C18 C17 120.4(3) . . ?
C18 C19 C20 120.2(3) . . ?
C21 C20 C19 119.9(3) . . ?
C20 C21 C16 120.3(3) . . ?
F1 C23 S1 111.9(2) . . ?
F2 C23 S1 111.68(19) . . ?
F2 C23 F1 107.2(2) . . ?
F3 C23 S1 111.3(2) . . ?
F3 C23 F1 107.2(2) . . ?
F3 C23 F2 107.3(2) . . ?
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 C9 2.094(3) . ?
I2 C17 2.092(3) . ?
S1 O1 1.438(2) . ?
S1 O2 1.442(2) . ?
S1 O3 1.440(2) . ?
S1 C23 1.827(3) . ?
F1 C23 1.337(3) . ?
F2 C23 1.336(3) . ?
F3 C23 1.335(3) . ?
N1 C1 1.365(4) . ?
N1 C5 1.365(3) . ?
N1 C22 1.490(3) . ?
C1 C2 1.391(4) . ?
C1 C6 1.421(4) . ?
C2 C3 1.378(4) . ?
C3 C4 1.389(4) . ?
C4 C5 1.387(4) . ?
C5 C14 1.424(4) . ?
C6 C7 1.197(4) . ?
C7 C8 1.433(4) . ?
C8 C9 1.412(4) . ?
C8 C13 1.407(4) . ?
C9 C10 1.384(4) . ?
C10 C11 1.387(4) . ?
C11 C12 1.386(4) . ?
C12 C13 1.375(4) . ?
C14 C15 1.198(4) . ?
C15 C16 1.434(4) . ?
C16 C17 1.398(4) . ?
C16 C21 1.403(4) . ?
C17 C18 1.388(4) . ?
C18 C19 1.387(4) . ?
C19 C20 1.388(5) . ?
C20 C21 1.383(4) . ?
