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_1549582
_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         'C36 H44 F I2 N3, 2(I)'
_chemical_formula_sum            'C36 H44 F I4 N3'
_chemical_formula_weight         1045.34
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-21
_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                90
_cell_angle_beta                 111.458(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.086(3)
_cell_length_b                   18.092(3)
_cell_length_c                   13.3174(18)
_cell_measurement_reflns_used    9280
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      24.857
_cell_measurement_theta_min      3.261
_cell_volume                     3831.3(11)
_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      100.0
_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 0.997
_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  0.0972
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            145488
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.133
_diffrn_reflns_theta_max         25.133
_diffrn_reflns_theta_min         3.060
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.286
_exptl_absorpt_correction_T_max  0.0912
_exptl_absorpt_correction_T_min  0.0532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1133 before and 0.0959 after correction. The Ratio of minimum to maximum transmission is 0.5833. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_description       plate
_exptl_crystal_F_000             2008
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.318
_refine_diff_density_min         -1.542
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         6814
_refine_ls_number_restraints     145
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0452P)^2^+28.7820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5271
_reflns_number_total             6814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01973h2.cif
_cod_data_source_block           umt_ob24a
_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_original_cell_volume        3831.4(9)
_cod_database_code               1549582
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.368
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2B = N2-H2A
 0.87 with sigma of 0.02
 C31-C30 \\sim C31B-C30
 with sigma of 0.02
 C32-C31 \\sim C32B-C31B
 with sigma of 0.02
 C33-C32 \\sim C32B-C33B
 with sigma of 0.02
 C33-C34 \\sim C33B-C34
 with sigma of 0.02
 C35-C36 \\sim C35B-C36B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C29, C30, C31, C32, C33, C34, C35, C36, C31B, C32B, C33B, C35B, C36B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C21, C21B, C22B, C22, C23, C24, C25, C26, C27, C28
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H23C)=Sof(H23D)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(C22B)=Sof(H22C)=
 Sof(H22D)=1-FVAR(1)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H23A)=Sof(H23B)=
 FVAR(1)
 Sof(H30C)=Sof(H30D)=Sof(H34C)=Sof(H34D)=Sof(C31B)=Sof(H31C)=Sof(H31D)=
 Sof(C32B)=Sof(H32C)=Sof(H32D)=Sof(C33B)=Sof(H33C)=Sof(H33D)=Sof(C35B)=
 Sof(H35C)=Sof(H35D)=Sof(C36B)=Sof(H36D)=Sof(H36E)=Sof(H36F)=1-FVAR(2)
 Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=
 Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H34A)=Sof(H34B)=Sof(C35)=Sof(H35A)=Sof(H35B)=
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C23(H23C,H23D), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C29(H29A,H29B),
 C30(H30A,H30B), C30(H30C,H30D), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B),
  C34(H34A,H34B), C34(H34C,H34D), C35(H35A,H35B), C21B(H21C,H21D), C22B(H22C,
 H22D), C31B(H31C,H31D), C32B(H32C,H32D), C33B(H33C,H33D), C35B(H35C,H35D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C11(H11), C17(H17), C18(H18), C20(H20)
5.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C36(H36A,H36B,H36C), C36B(H36D,H36E,H36F)
;
_shelx_res_checksum              79012
_olex2_submission_special_instructions 'No special instructions were received'