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_7228932
_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         '2(C2 F4 I2), C7 H9 N O'
_chemical_formula_sum            'C11 H9 F8 I4 N O'
_chemical_formula_weight         830.79
_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                 90.345(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8260(10)
_cell_length_b                   19.3955(8)
_cell_length_c                   13.3936(6)
_cell_measurement_reflns_used    10523
_cell_measurement_temperature    123.0(1)
_cell_measurement_theta_max      28.8180
_cell_measurement_theta_min      3.4590
_cell_volume                     4111.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_publication_material
'OLEX2 (Dolomanov et al., 2009) & WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      123.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26758
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         28.946
_diffrn_reflns_theta_min         2.998
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.108
_exptl_absorpt_correction_T_max  0.773
_exptl_absorpt_correction_T_min  0.326
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
 a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2992
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.952
_refine_diff_density_min         -1.499
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         9592
_refine_ls_number_restraints     2355
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0450P)^2^+10.0041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8589
_reflns_number_total             9592
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01381g2.cif
_cod_data_source_block           4_DI2
_cod_database_code               7228932
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.286
_shelx_estimated_absorpt_t_max   0.496
_shelx_res_checksum              59001
_shelx_hkl_checksum              8755