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_7123165
_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_absolute_configuration ad
_chemical_formula_moiety         'C8 H8 I2 O2 S'
_chemical_formula_sum            'C8 H8 I2 O2 S'
_chemical_formula_weight         422.00
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
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_audit_update_record
;
2019-02-04 deposited with the CCDC.    2019-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.0268(7)
_cell_length_b                   7.3586(3)
_cell_length_c                   8.0423(3)
_cell_measurement_reflns_used    9530
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      39.57
_cell_measurement_theta_min      2.75
_cell_volume                     1126.01(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.966
_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  0.0224
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            61066
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         39.807
_diffrn_reflns_theta_min         2.533
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    5.739
_exptl_absorpt_correction_T_max  0.4105
_exptl_absorpt_correction_T_min  0.2812
_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    2.489
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 2782 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.002(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         6641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.191
_refine_ls_R_factor_all          0.0145
_refine_ls_R_factor_gt           0.0139
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0085P)^2^+0.3143P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0286
_refine_ls_wR_factor_ref         0.0287
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                6532
_reflns_number_total             6641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01092k2.cif
_cod_data_source_block           vd066
_cod_database_code               7123165
_shelx_estimated_absorpt_t_min   0.269
_shelx_estimated_absorpt_t_max   0.571
_shelxl_version_number           2013-2
_shelx_res_checksum              8327
_shelx_hkl_checksum              23407