Supramolecular Networks by Imine Halogen Bonding
Nieland, Esther; Komisarek, Daniel; Hohloch, Stephan; Wurst, Klaus; Vasylyeva, Vera; Weingart, Oliver; Schmidt, Bernd M.; Chemical Communications  (2022) –; doi:10.1039/D2CC00799A

data_7129911
_publ_section_title
;
 Supramolecular Networks by Imine Halogen Bonding
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00799A
_journal_year                    2022
_chemical_formula_moiety         'C6 F5 I, C48 H48 N6, C H4 O'
_chemical_formula_sum            'C55 H52 F5 I N6 O'
_chemical_formula_weight         1034.92
_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   geom
_audit_creation_date             2022-03-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-18 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                116.465(5)
_cell_angle_beta                 108.720(5)
_cell_angle_gamma                90.484(7)
_cell_formula_units_Z            2
_cell_length_a                   12.0972(18)
_cell_length_b                   15.049(3)
_cell_length_c                   15.5995(18)
_cell_measurement_reflns_used    9122
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.890
_cell_measurement_theta_min      2.622
_cell_volume                     2369.1(7)
_computing_cell_refinement       'SAINT V8.40A (2016)'
_computing_data_collection       'Bruker Apex3 suite, 2021'
_computing_data_reduction        'SAINT V8.40A (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      153.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'omega phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            80779
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_min         1.806
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1232 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.9064.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       block
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         9695
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0285P)^2^+2.0023P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7992
_reflns_number_total             9695
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00799a2.cif
_cod_data_source_block           sh_bms_034_0m
_cod_original_cell_volume        2369.1(6)
_cod_database_code               7129911
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details   'Blessing, 1995'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C101-I10A
 2.01 with sigma of 0.01
 C100-F11A
 1.34 with sigma of 0.01
 C105-F11A
 2.35 with sigma of 0.01
 C101-F11A
 2.35 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(F11A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Sof(I10A)=Sof(F11A)=1-FVAR(1)
 Sof(I10)=Sof(F11)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C10(H10A,H10B), C30(H30A,H30B), C39(H39A,H39B), C20(H20A,
 H20B), C29(H29A,H29B)
5.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C23(H23), C31(H31), C13(H13), C33(H33), C11(H11), C18(H18),
 C38(H38), C28(H28), C25(H25), C37(H37), C17(H17), C35(H35), C27(H27), C36(H36),
  C16(H16), C15(H15), C26(H26)
5.c Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C7(H7A,H7B,H7C), C9A(H9AA,H9AB,H9AC), C9(H9A,H9B,H9C),
 C8(H8A,H8B,H8C), C8A(H8AA,H8AB,H8AC), C200(H20C,H20D,H20E)
5.d Idealised tetrahedral OH refined as rotating group:
 O200(H200)
;
_shelx_res_checksum              48012
_shelx_hkl_checksum              27716
_olex2_submission_special_instructions 'No special instructions were received'