The interplay between hydrogen and halogen bonding: substituent effects and their role in the hydrogen bond enhanced halogen bond.
Sun, Jiyu; Decato, Daniel A.; Bryantsev, Vyacheslav S.; John, Eric A.; Berryman, Orion B.; Chemical science 14 (2023) 8924–8935; doi:10.1039/d3sc02348f

data_1569562
_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         'C25 H10 F9 I2 N'
_chemical_formula_sum            'C25 H10 F9 I2 N'
_chemical_formula_weight         749.14
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-29
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.370(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0483(14)
_cell_length_b                   4.7023(4)
_cell_length_c                   30.687(3)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    105
_cell_measurement_theta_max      27.366
_cell_measurement_theta_min      3.074
_cell_volume                     2393.4(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      105
_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       '\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  0.0667
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            51830
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_min         3.073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.714
_exptl_absorpt_correction_T_max  0.6468
_exptl_absorpt_correction_T_min  0.5063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0760 before and 0.0603 after correction. The Ratio of minimum to maximum transmission is 0.7828. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.079
_exptl_crystal_description       needle
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.080
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5489
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0364
_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/[\s^2^(Fo^2^)+(0.0353P)^2^+4.0864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0805
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4239
_reflns_number_total             5489
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02348f2.cif
_cod_data_source_block           umt_ob112
_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        2393.4(3)
_cod_database_code               1569562
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.368
_olex2_refinement_description
;
1. Restrained distances
 N1-H1B = N1-H1A
 0.87 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C11(H11), C12(H12), C14(H14), C19(H19), C20(H20), C22(H22)
;
_shelx_res_checksum              68221
_olex2_submission_special_instructions 'No special instructions were received'