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_7228930
_publ_section_title
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 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         'C6 H7 N O'
_chemical_formula_sum            'C6 H7 N O'
_chemical_formula_weight         109.13
_space_group_crystal_system      tetragonal
_space_group_IT_number           141
_space_group_name_Hall           '-I 4bd 2'
_space_group_name_H-M_alt        'I 41/a m d'
_symmetry_space_group_name_Hall  '-I 4bd 2'
_symmetry_space_group_name_H-M   'I 41/a m d :2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
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_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
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.920(3)
_cell_length_b                   7.920(3)
_cell_length_c                   19.588(4)
_cell_measurement_reflns_used    1504
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.407
_cell_volume                     1228.7(7)
_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      170.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1126
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4574
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.878
_diffrn_reflns_theta_min         2.774
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.4695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0895 before and 0.0624 after correction.
The Ratio of minimum to maximum transmission is 0.6295.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     29
_refine_ls_number_reflns         454
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1579
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+1.6047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1644
_reflns_Friedel_coverage         0.000
_reflns_number_gt                189
_reflns_number_total             454
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01381g2.cif
_cod_data_source_block           3
_cod_original_cell_volume        1228.7(10)
_cod_database_code               7228930
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups
2. Others
 Fixed Sof: H4B(0.5) H4A(0.25)
3.a Riding coordinates:
 C4(H4B,H4A)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
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_shelx_res_checksum              22757
_shelx_hkl_checksum              43276
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'