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_1569571
_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 H16 F3 I2 N, C16 H36 N, Cl'
_chemical_formula_sum            'C41 H52 Cl F3 I2 N2'
_chemical_formula_weight         919.09
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-13
_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                107.965(2)
_cell_angle_beta                 108.3600(10)
_cell_angle_gamma                93.925(2)
_cell_formula_units_Z            2
_cell_length_a                   12.2702(5)
_cell_length_b                   13.0397(5)
_cell_length_c                   14.4541(6)
_cell_measurement_reflns_used    9515
_cell_measurement_temperature    100
_cell_measurement_theta_max      35.683
_cell_measurement_theta_min      2.655
_cell_volume                     2052.49(15)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0233
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            119487
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.654
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_correction_T_min  0.5589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0735 before and 0.0444 after correction. The Ratio of minimum to maximum transmission is 0.7482. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       prisim
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.81
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.374
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         9379
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0232
_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^)+(0.0206P)^2^+3.2063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0590
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8469
_reflns_number_total             9379
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02348f2.cif
_cod_data_source_block           umt_ob196
_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_database_code               1569571
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.840
_shelx_estimated_absorpt_t_min   0.350
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F3A-C24 \\sim F2-C24 \\sim F2AA-C24 \\sim F2A-C24 \\sim F3-C24 \\sim F0AA-C24
\\sim F1A-C24 \\sim F1-C24
 \\sim F1AA-C24
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C29 \\sim C29A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
4. Rigid body (RIGU) restrains
 F1, F2, F3, C24, F1A, F2A, F3A, F0AA, F1AA, F2AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 1*[Sof(F1A)+Sof(F2A)+Sof(F3A)]+1*[Sof(F1)+Sof(F2)+Sof(F3)]+1*[Sof(F0AA)+
 Sof(F1AA)+Sof(F2AA)]=1 with esd of 0.0001
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2)
 Sof(F0AA)=Sof(F1AA)=Sof(F2AA)=FVAR(3)
 Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(4)
 Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(4)
6.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C28(H28C,H28D), C30(H30A,
 H30B), C31(H31A,H31B), C32(H32A,H32B), C34(H34A,H34B), C35(H35A,H35B),
 C36(H36A,H36B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C11(H11), C13(H13), C19(H19), C20(H20), C22(H22)
6.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C29(H29A,H29B,H29C), C33(H33A,H33B,
 H33C), C37(H37A,H37B,H37C), C41(H41A,H41B,H41C), C29A(H29D,H29E,H29F)
;
_shelx_res_checksum              74581
_olex2_submission_special_instructions 'No special instructions were received'