Pushing the limits of the hydrogen bond enhanced halogen bond—the case of the C–H hydrogen bond
Decato, Daniel A.; Sun, Jiyu; Boller, Madeleine R.; Berryman, Orion B.; Chemical Science 13 (2022) 11156–11162; doi:10.1039/D2SC03792K

data_1567611
_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       '\w and \f 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
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_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 \l/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/[\s^2^(Fo^2^)+(0.0126P)^2^+1.9348P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              3845
_shelx_hkl_checksum              87078
_olex2_submission_special_instructions 'No special instructions were received'