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_7123166
_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         'C12 H10 N2, 2(C8 H8 O2 I2 S)'
_chemical_formula_sum            'C28 H26 I4 N2 O4 S2'
_chemical_formula_weight         1026.23
_chemical_name_systematic
;
 ?
;
_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
_atom_sites_solution_secondary   difmap
_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                114.136(2)
_cell_angle_beta                 90.987(2)
_cell_angle_gamma                97.782(2)
_cell_formula_units_Z            4
_cell_length_a                   11.1342(6)
_cell_length_b                   17.3124(10)
_cell_length_c                   19.0131(11)
_cell_measurement_reflns_used    9172
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.27
_cell_volume                     3303.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
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
;
SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., 
Giacovazzo, C., Polidori, G. & Spagna, R. (2003). 
J. Appl. Cryst. 36, 1103.)
;
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            217267
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.317
_diffrn_reflns_theta_min         1.177
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    3.935
_exptl_absorpt_correction_T_max  0.4426
_exptl_absorpt_correction_T_min  0.3530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.064
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         4.637
_refine_diff_density_min         -2.621
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         15974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0082P)^2^+20.6526P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0628
_reflns_number_gt                14207
_reflns_number_total             15974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01092k2.cif
_cod_data_source_block           VD057
_cod_database_code               7123166