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_7118325
_publ_section_title
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 Very strong (-)N-X(+)(-)O-N(+) halogen bonds.
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_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         'C12 H9 I N2 O4 S'
_chemical_formula_sum            'C12 H9 I N2 O4 S'
_chemical_formula_weight         404.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-09
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
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2015-09-21 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.68(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1370(14)
_cell_length_b                   22.707(5)
_cell_length_c                   8.8248(18)
_cell_measurement_temperature    170
_cell_volume                     1430.0(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0642
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8791
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_min         1.794
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.398
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0839 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.7159.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.779
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0614
_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^)+(0.0204P)^2^+10.8462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1946
_reflns_number_total             2576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc09487a2.cif
_cod_data_source_block           1_NISac
_cod_depositor_comments
'Adding full bibliography for 7118322--7118329.cif.'
_cod_original_cell_volume        1430.1(5)
_cod_database_code               7118325
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.719(2) 0.281(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C5) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C1(H1), C2(H2), C9(H9), C10(H10), C11(H11), C12(H12)
4.b Fitted hexagon refined as free rotating group:
 C3(C4,C5,N1,C1,C2)
;
_shelx_res_checksum              66466
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'