The intramolecular hydrogen bonded-halogen bond: a new strategy for preorganization and enhanced binding.
Riel, Asia Marie S.; Decato, Daniel A.; Sun, Jiyu; Massena, Casey J.; Jessop, Morly J.; Berryman, Orion B.; Chemical science 9 (2018) 5828–5836; doi:10.1039/c8sc01973h

data_1549579
_publ_section_title
;
 The intramolecular hydrogen bonded-halogen bond: a new strategy for
 preorganization and enhanced binding.
;
_journal_issue                   26
_journal_name_full               'Chemical science'
_journal_page_first              5828
_journal_page_last               5836
_journal_paper_doi               10.1039/c8sc01973h
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C22 H16 F I2 N3, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H16 F7 I2 N3 O6 S2'
_chemical_formula_weight         893.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-02-22 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                99.618(2)
_cell_angle_beta                 91.239(2)
_cell_angle_gamma                104.624(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0582(3)
_cell_length_b                   11.0044(4)
_cell_length_c                   17.7067(6)
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.026
_cell_measurement_theta_min      2.938
_cell_volume                     1494.58(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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  0.0515
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44120
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.087
_diffrn_reflns_theta_max         25.087
_diffrn_reflns_theta_min         2.938
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.332
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0631 before and 0.0562 after correction. The Ratio of minimum to maximum transmission is 0.8920. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.985
_exptl_crystal_description       needle
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.052
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         5299
_refine_ls_number_restraints     527
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0426P)^2^+3.6052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4480
_reflns_number_total             5299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01973h2.cif
_cod_data_source_block           g2xbmeotf
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1549577--1549583.cif.
;
_cod_database_code               1549579
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.561
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F5-C24 \\sim F5'-C24
 with sigma of 0.02
 S1-C23 \\sim S1'-C23'
 with sigma of 0.02
 S1-O3 \\sim S1'-O3' \\sim S1-O1 \\sim S1'-O1' \\sim S1-O2 \\sim S1'-O2'
 with sigma of 0.02
 F3-C23 \\sim F3'-C23' \\sim F4-C23 \\sim F4'-C23' \\sim F2-C23 \\sim F2'-C23'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C23) = Uanis(C23')
Uanis(C5) = Uanis(C5')
Uanis(C24') = Uanis(C24)
Uanis(O5) = Uanis(O5')
4. Rigid body (RIGU) restrains
 S1', O1', O2', O3', C23', F2', F3', F4'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O2, S1, O1, O3, C23, F2, F3, F4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O6, S2, O4, C24, F5, F7, F6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O4', S2', O5', O6', C24', F5', F6, F7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, I1, C1, C5, C2, C4, C6, N3, H2, H4, C3, C7, C5', C21, H3, C8, C1', C0AA,
 H21A, H21B, H21C, C9, I1', C2', C3', H0AA, H9, C10, N2, C13, H2', N3', H3', F1,
  C11, H2A, H2B, C14, C21', H11, C15, H21D, H21E, H21F, C16, C17, C19, H17, C18,
  I2, C20, N1, H18, H20, C22, H22A, H22B, H22C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(I1')=Sof(S2')=Sof(F5')=Sof(O4')=Sof(O5')=Sof(O6')=Sof(C5')=Sof(C1')=
 Sof(C2')=Sof(H2')=Sof(N3')=Sof(C3')=Sof(H3')=Sof(C0AA)=Sof(H0AA)=Sof(C21')=
 Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C24')=Sof(S1')=Sof(F2')=Sof(F3')=Sof(F4')=
 Sof(O1')=Sof(O2')=Sof(O3')=Sof(C23')=1-FVAR(1)
 Sof(I1)=Sof(S2)=Sof(F5)=Sof(O4)=Sof(O5)=Sof(O6)=Sof(C5)=Sof(C4)=Sof(H4)=
 Sof(C3)=Sof(H3)=Sof(N3)=Sof(C2)=Sof(H2)=Sof(C1)=Sof(C21)=Sof(H21A)=Sof(H21B)=
 Sof(H21C)=Sof(C24)=Sof(S1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(O1)=Sof(O2)=Sof(O3)=
 Sof(C23)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2), C9(H9), C11(H11), C17(H17), C18(H18), C20(H20),
 C2'(H2'), C3'(H3'), C0AA(H0AA)
6.b Fitted hexagon refined as free rotating group:
 C5(C4,C3,N3,C2,C1), C5'(C1',C2',N3',C3',C0AA)
6.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
6.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C21'(H21D,H21E,H21F)
;
_shelx_res_checksum              52440
_olex2_submission_special_instructions 'No special instructions were received'