Nontypical iodine–halogen bonds in the crystal structure of (3<i>E</i>)-8-chloro-3-iodomethylidene-2,3-dihydro-1,4-oxazino[2,3,4-<i>ij</i>]quinolin-4-ium triiodide
Bartashevich, E. V.; Batalov, V. I.; Yushina, I. D.; Stash, A. I.; Chen, Y. S.; Acta Crystallographica Section C 72 (2016) 341–345; doi:10.1107/S2053229616003934

data_2020445
_publ_contact_author             'Adam Stash'
_publ_section_title
;
 Nontypical iodine--halogen bonds in the crystal structure of
 (3<i>E</i>)-8-chloro-3-iodomethylidene-2,3-dihydro-1,4-oxazino[2,3,4-<i>ij</i>]quinolin-4-ium
 triiodide
;
_journal_coeditor_code           LG3186
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              341
_journal_page_last               345
_journal_paper_doi               10.1107/S2053229616003934
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C12 H8 Cl I N O +, I3 -'
_chemical_formula_moiety         'C12 H8 Cl I N O +, I3 -'
_chemical_formula_sum            'C12 H8 Cl I4 N O'
_chemical_formula_weight         725.24
_chemical_name_systematic
'(3<i>E</i>)-8-Chloro-3-iodomethylidene-2,3-dihydro-1,4-oxazino[2,3,4-<i>ij</i>]quinolin-4-ium triiodide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 101.6439(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6227(2)
_cell_length_b                   13.9464(4)
_cell_length_c                   16.0161(4)
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      17.160
_cell_measurement_theta_min      2.324
_cell_volume                     1667.62(8)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2013) and <i>ACD</i>/<i>ChemSketch</i>
(Advanced Chemistry Development Inc., 2015)
;
_computing_publication_material
;
SHELXTL (Bruker, 2013)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       \f-scan
_diffrn_radiation_monochromator  'diamond (111)'
_diffrn_radiation_source         'Advanced photon source'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            45635
_diffrn_reflns_theta_full        14.357
_diffrn_reflns_theta_max         17.172
_diffrn_reflns_theta_min         1.510
_exptl_absorpt_coefficient_mu    1.753
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2013)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.889
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.042
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.522
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         5066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0163
_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^)+(0.0066P)^2^+1.3647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0336
_refine_ls_wR_factor_ref         0.0350
_reflns_number_gt                4500
_reflns_number_total             5066
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lg3186sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2020445.cif.'
_cod_database_code               2020445
_cod_database_fobs_code          2020445
_shelx_hkl_checksum              63563
_shelx_res_checksum              18434
_shelxl_version_number           2.013