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_1569568
_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
'C23 H12 F3 I2 N, C21 H43 N, 1.25(Cl), C6 H12.69 N0.25'
_chemical_formula_sum            'C50 H67.69 Cl1.25 F3 I2 N2.25'
_chemical_formula_weight         1055.37
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-14
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.9115(18)
_cell_length_b                   36.9115(18)
_cell_length_c                   8.3724(4)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.982
_cell_measurement_theta_min      2.49
_cell_volume                     11407.1(10)
_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 0.998
_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  0.0551
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            86060
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.468
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.201
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1149 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.7676. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       needle
_exptl_crystal_F_000             4302
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 4004 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.034(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         10071
_refine_ls_number_restraints     92
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0237P)^2^+43.3286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                9215
_reflns_number_total             10071
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02348f2.cif
_cod_data_source_block           ob148_sq
_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        11407.0(12)
_cod_database_code               1569568
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H49,H49A,H49B} of C49, All C(H,H) groups
 At 1.5 times of:
  {H41A,H41B,H41C} of C41, {H35A,H35B,H35C} of C35, {H29A,H29B,H29C} of C29,
  {H50D,H50E,H50F} of C50A, {H50A,H50B,H50C} of C50
2. Restrained distances
 N1-H1B = N1-H1A
 0.87 with sigma of 0.02
 F1-C23 \\sim F3A-C23 \\sim F3-C23 \\sim F2A-C23 \\sim F2-C23 \\sim F1A-C23
 with sigma of 0.02
 C50-C49 \\sim C50A-C49
 with sigma of 0.02
3. Restrained planarity
 N1, H1A, H1B, C9, C14
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F1A \\sim F2A \\sim F3A: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 F1, F2, F3, C23, F1A, F2A, F3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C43
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(H49A)=Sof(H49B)=Sof(C50A)=Sof(H50D)=Sof(H50E)=Sof(H50F)=1-FVAR(2)
 Sof(H49)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(H50C)=FVAR(2)
7.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,
 H28B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B),
 C34(H34A,H34B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B),
  C40(H40A,H40B), C42(H42A,H42B), C43(H43A,H43B), C45(H45A,H45B), C46(H46A,
 H46B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C12(H12), C19(H19), C20(H20),
 C21(H21), C22(H22), C49(H49)
7.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C35(H35A,H35B,H35C), C41(H41A,H41B,H41C), C50(H50A,H50B,
 H50C), C50A(H50D,H50E,H50F)
;
_shelx_res_checksum              92415
_shelx_fab_checksum              80432
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'