Tridentate C‒I⋯O−‒N+ halogen bonds
Topić, Filip; Puttreddy, Rakesh; Rautiainen, J. Mikko; Tuononen, Heikki M.; Rissanen, Kari; CrystEngComm  (2017) –; doi:10.1039/C7CE01381G

data_7228931
_publ_section_title
;
 Tridentate C--I&#x22EF;O&#x2212;--N+ halogen bonds
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01381G
_journal_year                    2017
_chemical_formula_moiety         '3.6(C4 F8 I2), 2(C9 H13 N O)'
_chemical_formula_sum            'C32.4 H26 F28.8 I7.2 N2 O2'
_chemical_formula_weight         1936.23
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-06-22 deposited with the CCDC.
2017-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.4035(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.6238(3)
_cell_length_b                   11.3737(3)
_cell_length_c                   21.9526(4)
_cell_measurement_reflns_used    6123
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      26.373
_cell_measurement_theta_min      0.407
_cell_volume                     3038.72(12)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) & WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '\f scans + \w scans'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22249
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         26.851
_diffrn_reflns_theta_min         2.033
_exptl_absorpt_coefficient_mu    3.793
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.116
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1782
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.047
_refine_diff_density_max         1.679
_refine_diff_density_min         -0.988
_refine_diff_density_rms         0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     643
_refine_ls_number_reflns         6428
_refine_ls_number_restraints     2839
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0944P)^2^+14.9138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1726
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5185
_reflns_number_total             6428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01381g2.cif
_cod_data_source_block           2_DI4
_cod_original_formula_sum        'C32.40 H26 F28.80 I7.20 N2 O2'
_cod_database_code               7228931
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.350
_shelx_estimated_absorpt_t_max   0.842
_shelx_res_checksum              46840
_shelx_hkl_checksum              7433