#------------------------------------------------------------------------------
#$Date: 2016-05-04 21:43:54 +0300 (Wed, 04 May 2016) $
#$Revision: 182546 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/04/2020445.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2020445
loop_
_publ_author_name
'Bartashevich, E. V.'
'Batalov, V. I.'
'Yushina, I. D.'
'Stash, A. I.'
'Chen, Y. S.'
_publ_contact_author             'Adam Stash'
_publ_section_title
;
 Nontypical iodine--halogen bonds in the crystal structure of
 (3E)-8-chloro-3-iodomethylidene-2,3-dihydro-1,4-oxazino[2,3,4-ij]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
'(3E)-8-Chloro-3-iodomethylidene-2,3-dihydro-1,4-oxazino[2,3,4-ij]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 ACD/ChemSketch
(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       φ-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/[σ²(Fo²)+(0.0066P)²+1.3647P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2.013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
I I1 0.66498(2) 0.62361(2) 0.89967(2) 0.01440(3) Uani d 1
I I2 0.73791(2) 0.93112(2) 0.88024(2) 0.01641(3) Uani d 1
I I3 0.56775(2) 0.82664(2) 0.72026(2) 0.01462(3) Uani d 1
I I4 0.41517(2) 0.71760(2) 0.57124(2) 0.01730(4) Uani d 1
Cl Cl1 0.31958(7) 0.08762(4) 0.56172(3) 0.01759(10) Uani d 1
O O1 0.5294(2) 0.31342(10) 0.87713(9) 0.0146(3) Uani d 1
N N1 0.3789(2) 0.40884(12) 0.72295(11) 0.0122(3) Uani d 1
C C1 0.2998(3) 0.45397(14) 0.65133(13) 0.0151(4) Uani d 1
H H1 0.2873 0.5217 0.6516 0.018 Uiso calc 1
C C2 0.2358(3) 0.40311(15) 0.57665(14) 0.0166(4) Uani d 1
H H2 0.1778 0.4360 0.5267 0.020 Uiso calc 1
C C3 0.2567(3) 0.30512(15) 0.57515(14) 0.0153(4) Uani d 1
H H3 0.2150 0.2705 0.5239 0.018 Uiso calc 1
C C4 0.3397(3) 0.25623(14) 0.64956(13) 0.0117(4) Uani d 1
C C5 0.3740(3) 0.15615(14) 0.65342(13) 0.0138(4) Uani d 1
C C6 0.4558(3) 0.11316(14) 0.72781(14) 0.0172(4) Uani d 1
H H6 0.4793 0.0462 0.7286 0.021 Uiso calc 1
C C7 0.5055(3) 0.16687(14) 0.80322(14) 0.0166(4) Uani d 1
H H7 0.5597 0.1356 0.8547 0.020 Uiso calc 1
C C8 0.4766(3) 0.26435(14) 0.80322(13) 0.0129(4) Uani d 1
C C9 0.3973(3) 0.30951(14) 0.72569(12) 0.0110(3) Uani d 1
C C10 0.4431(3) 0.40542(14) 0.87812(13) 0.0140(4) Uani d 1
H H101 0.5007 0.4417 0.9295 0.017 Uiso calc 1
H H102 0.3154 0.3961 0.8803 0.017 Uiso calc 1
C C11 0.4574(3) 0.46079(14) 0.79981(13) 0.0122(4) Uani d 1
C C12 0.5393(3) 0.54442(14) 0.79424(13) 0.0137(4) Uani d 1
H H12 0.5404 0.5692 0.7391 0.016 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0000 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0020 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.0550 0.0530 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -1.9000 0.6850 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
I4 I3 I2 176.897(6)
C8 O1 C10 113.73(15)
C1 N1 C9 121.30(17)
C1 N1 C11 121.96(17)
C9 N1 C11 116.66(16)
N1 C1 C2 121.02(19)
N1 C1 H1 119.5
C2 C1 H1 119.5
C3 C2 C1 119.96(19)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C4 119.99(19)
C2 C3 H3 120.0
C4 C3 H3 120.0
C3 C4 C5 124.10(19)
C3 C4 C9 118.81(18)
C5 C4 C9 117.08(18)
C6 C5 C4 121.13(19)
C6 C5 Cl1 119.11(16)
C4 C5 Cl1 119.72(16)
C5 C6 C7 120.76(19)
C5 C6 H6 119.6
C7 C6 H6 119.6
C8 C7 C6 120.67(19)
C8 C7 H7 119.7
C6 C7 H7 119.7
O1 C8 C7 118.60(18)
O1 C8 C9 122.72(17)
C7 C8 C9 118.66(19)
N1 C9 C8 119.55(17)
N1 C9 C4 118.81(17)
C8 C9 C4 121.62(18)
O1 C10 C11 109.83(17)
O1 C10 H101 109.7
C11 C10 H101 109.7
O1 C10 H102 109.7
C11 C10 H102 109.7
H101 C10 H102 108.2
C12 C11 N1 119.93(18)
C12 C11 C10 128.45(19)
N1 C11 C10 111.49(16)
C11 C12 I1 123.66(16)
C11 C12 H12 118.2
I1 C12 H12 118.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C12 2.082(2)
I2 I3 3.0048(2)
I3 I4 2.8708(2)
Cl1 C5 1.731(2)
O1 C8 1.356(2)
O1 C10 1.443(2)
N1 C1 1.340(3)
N1 C9 1.392(2)
N1 C11 1.450(3)
C1 C2 1.391(3)
C1 H1 0.9500
C2 C3 1.377(3)
C2 H2 0.9500
C3 C4 1.408(3)
C3 H3 0.9500
C4 C5 1.419(3)
C4 C9 1.420(3)
C5 C6 1.367(3)
C6 C7 1.407(3)
C6 H6 0.9500
C7 C8 1.377(3)
C7 H7 0.9500
C8 C9 1.414(3)
C10 C11 1.496(3)
C10 H101 0.9900
C10 H102 0.9900
C11 C12 1.334(3)
C12 H12 0.9500
