#------------------------------------------------------------------------------
#$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $
#$Revision: 252006 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240504.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7240504
loop_
_publ_author_name
'Fotović, Luka'
'Stilinovic, Vladimir'
_publ_section_title
;
 Halogenide anions as halogen and hydrogen bond acceptors in
 iodopyridinium halogenides
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00534G
_journal_year                    2020
_chemical_formula_sum            'C5 H5 Cl I N'
_chemical_formula_weight         241.45
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.886(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.4564(3)
_cell_length_b                   10.8438(7)
_cell_length_c                   14.8824(11)
_cell_measurement_reflns_used    1443
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      38.2095
_cell_measurement_theta_min      3.9931
_cell_volume                     716.57(9)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution
;
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112-122.
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1385
_diffrn_reflns_av_unetI/netI     0.1139
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5186
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.991
_diffrn_reflns_theta_min         4.002
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.238
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.885
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.800
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1550
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      0.797
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0413
_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/[σ²(Fo²)+(0.0155P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.000
_reflns_number_gt                883
_reflns_number_total             1550
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00534g2.cif
_cod_data_source_block           2-IPyHCl
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7240504
_shelx_shelxl_version_number     2018/3
_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.
;
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_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 0.55398(10) -0.03734(5) 0.85787(3) 0.05882(19) Uani 1 1 d . . . . .
Cl1 Cl 0.0646(5) 0.18139(17) 0.67268(11) 0.0703(6) Uani 1 1 d . . . . .
N1 N 0.5204(13) 0.2352(6) 0.8281(3) 0.0557(16) Uani 1 1 d . . . . .
H1 H 0.393098 0.212828 0.784445 0.067 Uiso 1 1 calc R U . . .
C4 C 0.9112(19) 0.3073(8) 0.9652(5) 0.081(3) Uani 1 1 d . U . . .
H4 H 1.039500 0.332536 1.014381 0.097 Uiso 1 1 calc R U . . .
C2 C 0.6597(15) 0.1474(6) 0.8820(4) 0.0512(18) Uani 1 1 d . . . . .
C3 C 0.8578(15) 0.1845(7) 0.9511(4) 0.065(2) Uani 1 1 d . U . . .
H3 H 0.956890 0.126375 0.988760 0.078 Uiso 1 1 calc R U . . .
C6 C 0.5751(17) 0.3532(8) 0.8410(4) 0.068(2) Uani 1 1 d . U . . .
H6 H 0.472219 0.410461 0.803372 0.082 Uiso 1 1 calc R U . . .
C5 C 0.7776(18) 0.3939(8) 0.9077(5) 0.081(2) Uani 1 1 d . U . . .
H5 H 0.824030 0.477222 0.914107 0.098 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C6 N1 C2 121.7(6) . . ?
C6 N1 H1 119.1 . . ?
C2 N1 H1 119.1 . . ?
C3 C4 C5 120.7(7) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C3 C2 N1 118.3(7) . . ?
C3 C2 I1 122.6(5) . . ?
N1 C2 I1 119.1(5) . . ?
C2 C3 C4 119.9(7) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
N1 C6 C5 121.8(7) . . ?
N1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C5 C4 117.4(8) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
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 C2 2.082(7) . ?
N1 C6 1.314(9) . ?
N1 C2 1.360(8) . ?
N1 H1 0.8600 . ?
C4 C3 1.366(10) . ?
C4 C5 1.372(10) . ?
C4 H4 0.9300 . ?
C2 C3 1.358(8) . ?
C3 H3 0.9300 . ?
C6 C5 1.357(8) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 0.6(10) . . . . ?
C6 N1 C2 I1 179.0(5) . . . . ?
N1 C2 C3 C4 0.3(11) . . . . ?
I1 C2 C3 C4 -178.0(6) . . . . ?
C5 C4 C3 C2 -3.1(13) . . . . ?
C2 N1 C6 C5 1.2(12) . . . . ?
N1 C6 C5 C4 -3.9(13) . . . . ?
C3 C4 C5 C6 4.8(14) . . . . ?
