#------------------------------------------------------------------------------
#$Date: 2021-07-16 08:08:54 +0300 (Fri, 16 Jul 2021) $
#$Revision: 267585 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/88/2108837.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_2108837
loop_
_publ_author_name
'Yushina, Irina'
'Krylov, Alexander'
'Leonidov, Ivan I.'
'Batalov, Vladimir'
'Chen, Yu-Sheng'
'Wang, Suyin Grass'
'Stash, Adam'
'Bartashevich, Ekaterina'
_publ_contact_author             'Adam Stash'
_publ_section_title
;
 The influence of chalcogen atom on conformation and phase transition in
 chalcogenazinoquinolinium monoiodides
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520621004571
_journal_volume                  77
_journal_year                    2021
_chemical_formula_moiety         'C12 H10  N O Cl I, I'
_chemical_formula_sum            'C12 H10 Cl I2 N O'
_chemical_formula_weight         473.46
_chemical_name_systematic
;
8-chloro-3-(iodomethyl)-2,3-dihydro-[1,4]oxazino[2,3,4-ij]
quinolin-4-ium monoiodide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 96.1485(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.7324(4)
_cell_length_b                   24.4482(7)
_cell_length_c                   8.2375(2)
_cell_measurement_reflns_used    9627
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.790
_cell_measurement_theta_min      2.570
_cell_volume                     2749.69(13)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_device_type
;
Huber 3 circle diffractometer with PILATUS3 X CdTe 1M detector
;
_diffrn_measurement_method       φ-scan
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41426
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            154365
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        14.392
_diffrn_reflns_theta_max         24.496
_diffrn_reflns_theta_min         0.971
_diffrn_source                   'Advanced photon source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.103
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2014/4 - Bruker AXS area detector scaling 
 and absorption correction 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.287
_exptl_crystal_description       prism
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.061
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.031
_refine_diff_density_max         1.613
_refine_diff_density_min         -1.706
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         10087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0247
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0319P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0648
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8037
_reflns_number_total             10087
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            xk5079sup1.cif
_cod_data_source_block           KB01
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2108837
_publcif_datablock.id            {dac57631-7ece-47d5-ad2e-5751958b0063}
_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.
;
_shelx_estimated_absorpt_t_min   0.936
_shelx_estimated_absorpt_t_max   0.967
_publcif_info_exptl_table_max_cols 5
_publcif_info_exptl_table_use_headnotes n
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.98096(2) 0.58483(2) 1.00429(2) 0.01881(2) Uani 1 1 d . . . . .
I2 I 0.76580(2) 0.62511(2) 0.33833(2) 0.01710(2) Uani 1 1 d . . . . .
Cl1 Cl 0.50011(3) 0.76195(2) 0.99506(5) 0.02884(7) Uani 1 1 d . . . . .
O1 O 0.62732(7) 0.53378(4) 0.89172(12) 0.02179(16) Uani 1 1 d . . . . .
N1 N 0.74591(8) 0.62207(4) 0.80335(12) 0.01572(15) Uani 1 1 d . . . . .
C1 C 0.79838(9) 0.66272(5) 0.74698(14) 0.01793(18) Uani 1 1 d . . . . .
H1A H 0.856908 0.654538 0.699989 0.022 Uiso 1 1 calc R U . . .
C2 C 0.76754(9) 0.71763(5) 0.75673(15) 0.01979(19) Uani 1 1 d . . . . .
H2A H 0.804212 0.746162 0.713922 0.024 Uiso 1 1 calc R U . . .
C3 C 0.68376(9) 0.72963(5) 0.82883(14) 0.01856(18) Uani 1 1 d . . . . .
H3A H 0.663080 0.766546 0.836210 0.022 Uiso 1 1 calc R U . . .
C4 C 0.54252(9) 0.69549(5) 0.97295(14) 0.01953(19) Uani 1 1 d . . . . .
C5 C 0.49252(9) 0.65179(6) 1.03226(16) 0.0230(2) Uani 1 1 d . . . . .
H5A H 0.437988 0.658333 1.091481 0.028 Uiso 1 1 calc R U . . .
C6 C 0.52246(9) 0.59753(6) 1.00483(15) 0.0215(2) Uani 1 1 d . . . . .
H6A H 0.486660 0.567863 1.043432 0.026 Uiso 1 1 calc R U . . .
C7 C 0.60318(9) 0.58705(5) 0.92255(14) 0.01783(18) Uani 1 1 d . . . . .
C8 C 0.62826(8) 0.68693(5) 0.89215(13) 0.01622(17) Uani 1 1 d . . . . .
C9 C 0.65916(8) 0.63172(4) 0.87182(13) 0.01526(16) Uani 1 1 d . . . . .
C10 C 0.77961(9) 0.56403(5) 0.79087(14) 0.01760(18) Uani 1 1 d . . . . .
H10A H 0.820041 0.560709 0.697353 0.021 Uiso 1 1 calc R U . . .
C11 C 0.68760(10) 0.52888(5) 0.75711(16) 0.0219(2) Uani 1 1 d . . . . .
H11A H 0.649702 0.540939 0.654331 0.026 Uiso 1 1 calc R U . . .
H11B H 0.706430 0.490165 0.744138 0.026 Uiso 1 1 calc R U . . .
C12 C 0.84024(9) 0.54540(5) 0.94802(14) 0.01893(18) Uani 1 1 d . . . . .
H12A H 0.851262 0.505505 0.940532 0.023 Uiso 1 1 calc R U . . .
H12B H 0.801058 0.551627 1.040443 0.023 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0001 0.0005 '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 0.0005 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0017 0.0018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.0557 0.0533 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -1.8844 0.6897 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C11 112.71(9) . . ?
C1 N1 C9 122.02(10) . . ?
C1 N1 C10 119.80(10) . . ?
C9 N1 C10 118.17(9) . . ?
N1 C1 C2 120.65(11) . . ?
N1 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
C3 C2 C1 119.65(11) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C8 120.31(10) . . ?
C2 C3 H3A 119.8 . . ?
C8 C3 H3A 119.8 . . ?
C5 C4 C8 121.01(11) . . ?
C5 C4 Cl1 119.86(9) . . ?
C8 C4 Cl1 119.13(9) . . ?
C4 C5 C6 120.19(11) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C7 C6 C5 120.93(12) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
O1 C7 C6 119.19(11) . . ?
O1 C7 C9 121.61(10) . . ?
C6 C7 C9 119.19(11) . . ?
C3 C8 C4 124.29(11) . . ?
C3 C8 C9 118.16(10) . . ?
C4 C8 C9 117.55(10) . . ?
N1 C9 C7 120.10(10) . . ?
N1 C9 C8 119.02(10) . . ?
C7 C9 C8 120.88(10) . . ?
N1 C10 C11 106.82(9) . . ?
N1 C10 C12 111.55(9) . . ?
C11 C10 C12 110.52(10) . . ?
N1 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C12 C10 H10A 109.3 . . ?
O1 C11 C10 109.93(9) . . ?
O1 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
O1 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C10 C12 I1 116.14(8) . . ?
C10 C12 H12A 108.3 . . ?
I1 C12 H12A 108.3 . . ?
C10 C12 H12B 108.3 . . ?
I1 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C12 2.1648(12) . ?
Cl1 C4 1.7421(13) . ?
O1 C7 1.3743(15) . ?
O1 C11 1.4580(16) . ?
N1 C1 1.3394(15) . ?
N1 C9 1.3917(15) . ?
N1 C10 1.4993(14) . ?
C1 C2 1.4127(16) . ?
C1 H1A 0.9500 . ?
C2 C3 1.3816(17) . ?
C2 H2A 0.9500 . ?
C3 C8 1.4241(16) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3868(19) . ?
C4 C8 1.4287(16) . ?
C5 C6 1.414(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.3837(17) . ?
C6 H6A 0.9500 . ?
C7 C9 1.4237(16) . ?
C8 C9 1.4302(15) . ?
C10 C11 1.5287(18) . ?
C10 C12 1.5316(16) . ?
C10 H10A 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
loop_
_publcif_info_cif.paper_type
CB
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{dbc98eae-4d1d-4e7d-9e09-99afb1cee94c} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{c729a655-eabd-4f8c-a5ec-06a1023ba6af} y y y
{dbc98eae-4d1d-4e7d-9e09-99afb1cee94c} y y y
{dac57631-7ece-47d5-ad2e-5751958b0063} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_exptl_table_header_item
Datablock_name

_cod_database_fobs_code 2108837
