Very strong (-)N-X(+)(-)O-N(+) halogen bonds.
Puttreddy, Rakesh; Jurček, Ondřej; Bhowmik, Sandip; Mäkelä, Toni; Rissanen, Kari; Chemical communications (Cambridge, England) 52 (2016) 2338–2341; doi:10.1039/c5cc09487a

data_7118326
_publ_section_title
;
 Very strong (-)N-X(+)(-)O-N(+) halogen bonds.
;
_journal_issue                   11
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2338
_journal_page_last               2341
_journal_paper_doi               10.1039/c5cc09487a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C13 H11 I N2 O4 S'
_chemical_formula_sum            'C13 H11 I N2 O4 S'
_chemical_formula_weight         418.20
_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
_audit_creation_date             2015-08-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-09-21 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                109.12(3)
_cell_angle_beta                 99.97(3)
_cell_angle_gamma                90.54(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2705(15)
_cell_length_b                   8.7631(18)
_cell_length_c                   12.765(3)
_cell_measurement_temperature    170
_cell_volume                     754.9(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0266
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7107
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         25.243
_diffrn_reflns_theta_min         1.719
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.275
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0687 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.7845.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0184P)^2^+0.8524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0606
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2489
_reflns_number_total             2738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc09487a2.cif
_cod_data_source_block           2_NISac
_cod_depositor_comments
'Adding full bibliography for 7118322--7118329.cif.'
_cod_database_code               7118326
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              9826
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'