Diiodomethyl-sulfonyl moiety: An unexplored halogen bond-donor motif
Dichiarante, Valentina; Kaiho, Tatsuo; Metrangolo, Pierangelo; Pilati, Tullio; Resnati, Giuseppe; Terraneo, Giancarlo; Ursini, Maurizio; Chemical Communications  (2019) –; doi:10.1039/C9CC01092K

data_7123167
_publ_section_title
;
 Diiodomethyl-sulfonyl moiety: An unexplored halogen bond-donor motif
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01092K
_journal_year                    2019
_chemical_formula_moiety         'C8 H8 I2 O2 S, C10 H8 N2'
_chemical_formula_sum            'C18 H16 I2 N2 O2 S'
_chemical_formula_weight         578.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-02-04 deposited with the CCDC.    2019-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                93.590(5)
_cell_angle_beta                 96.031(5)
_cell_angle_gamma                114.648(5)
_cell_formula_units_Z            2
_cell_length_a                   8.6591(8)
_cell_length_b                   9.7178(8)
_cell_length_c                   13.0375(15)
_cell_measurement_reflns_used    5666
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      32.70
_cell_measurement_theta_min      2.62
_cell_volume                     984.70(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS (Sheldrick, 2013)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15401
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.976
_diffrn_reflns_theta_min         3.699
_diffrn_source                   'sealed tube'
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    3.313
_exptl_absorpt_correction_T_max  0.5297
_exptl_absorpt_correction_T_min  0.4751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.950
_exptl_crystal_description       wedge
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.286
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         6968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0254P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0651
_reflns_number_gt                5426
_reflns_number_total             6968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01092k2.cif
_cod_data_source_block           vd027b
_cod_database_code               7123167
_shelx_estimated_absorpt_t_min   0.480
_shelx_estimated_absorpt_t_max   0.826
_shelxl_version_number           2013-2
_shelx_res_checksum              66212
_shelx_hkl_checksum              92409