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_7118328
_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         'C7 H5 N O3 S, C5 H5 N O'
_chemical_formula_sum            'C12 H10 N2 O4 S'
_chemical_formula_weight         278.28
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-18
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_audit_update_record
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2015-09-21 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                98.755(5)
_cell_angle_beta                 106.766(5)
_cell_angle_gamma                93.582(5)
_cell_formula_units_Z            2
_cell_length_a                   6.8571(4)
_cell_length_b                   8.4482(5)
_cell_length_c                   11.3117(6)
_cell_measurement_reflns_used    2588
_cell_measurement_temperature    123
_cell_measurement_theta_max      28.6700
_cell_measurement_theta_min      3.8180
_cell_volume                     616.19(6)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -87.00   12.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368  -77.0000   30.0000 99

  2 omega  -86.00    7.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368  -19.0000 -150.0000 93

  3 omega  -44.00   46.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368   77.0000  150.0000 90

  4 omega  -93.00  -40.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.1368 -178.0000  120.0000 53

  5 omega   24.00   61.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3868  -99.0000  -60.0000 37
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.0291600000
_diffrn_orient_matrix_UB_12      0.0829525000
_diffrn_orient_matrix_UB_13      0.0258948000
_diffrn_orient_matrix_UB_21      -0.0958153000
_diffrn_orient_matrix_UB_22      0.0055450000
_diffrn_orient_matrix_UB_23      0.0116434000
_diffrn_orient_matrix_UB_31      0.0423024000
_diffrn_orient_matrix_UB_32      -0.0199203000
_diffrn_orient_matrix_UB_33      0.0601937000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4086
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_min         3.122
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88977
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.2357
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.0497
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2224
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0434P)^2^+0.3115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1015
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1968
_reflns_number_total             2224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc09487a2.cif
_cod_data_source_block           1_NSacH
_cod_depositor_comments
'Adding full bibliography for 7118322--7118329.cif.'
_cod_database_code               7118328
_chemical_oxdiff_formula         'C10 H10 N2 S1 O3'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N2-H2
 1 with sigma of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5)
;
_shelx_res_checksum              56663
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'