#------------------------------------------------------------------------------
#$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $
#$Revision: 252006 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240506.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_7240506
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 I2 N'
_chemical_formula_weight         332.90
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0849(7)
_cell_length_b                   4.7247(2)
_cell_length_c                   11.2538(4)
_cell_measurement_reflns_used    4246
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.2759
_cell_measurement_theta_min      3.8616
_cell_volume                     802.08(6)
_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    'SHELXS-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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  0.0294
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6146
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         4.314
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    7.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60257
_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            yellow
_exptl_crystal_density_diffrn    2.757
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 657 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_coef       0.0261(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1695
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.871
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0191
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0282P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0413
_refine_ls_wR_factor_ref         0.0422
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                1538
_reflns_number_total             1695
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00534g2.cif
_cod_data_source_block           2-IPyHI
_cod_database_code               7240506
_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.
;
_shelx_res_file
;
TITL shelxt_a.res in Pca2(1)
    shelx.res
    created by SHELXL-2018/3 at 14:55:00 on 26-Jun-2019
CELL  0.71073  15.0849   4.7247  11.2538   90.000   90.000   90.000
ZERR     4.00   0.0007   0.0002   0.0004    0.000    0.000    0.000
LATT  -1
SYMM  - X, - Y, 1/2 + Z
SYMM  1/2 + X, - Y,   Z
SYMM  1/2 - X,   Y, 1/2 + Z
SFAC  C    H    N    I
UNIT  20   20   4    8
MERG   2
OMIT    -4.00  54.00
FMAP   2
PLAN   20
ACTA
BOND
LIST   6
L.S.  20
WGHT    0.028200
EXTI    0.026058
FVAR       4.59412
I1    4    0.375387    0.711737    0.706634    11.00000    0.04653    0.05633 =
         0.03997   -0.00365    0.00231    0.00086
I2    4    0.599447    1.129524    0.505544    11.00000    0.04857    0.04567 =
         0.04121    0.00227   -0.00169   -0.00545
C2    1    0.366597    0.582202    0.528878    11.00000    0.03486    0.04346 =
         0.03935    0.00256   -0.00241    0.00998
C3    1    0.306538    0.386580    0.490497    11.00000    0.03812    0.05199 =
         0.04923    0.00218   -0.00294   -0.00435
AFIX  43
H3    2    0.265636    0.308352    0.542887    11.00000   -1.20000
AFIX   0
N1    3    0.424035    0.694862    0.451057    11.00000    0.03786    0.04174 =
         0.04147   -0.00240    0.00005    0.00065
AFIX  43
H1    2    0.462392    0.815874    0.475862    11.00000   -1.20000
AFIX   0
C4    1    0.307598    0.305767    0.370847    11.00000    0.05420    0.05127 =
         0.05221   -0.00063   -0.01395   -0.00513
AFIX  43
H4    2    0.268328    0.168797    0.343432    11.00000   -1.20000
AFIX   0
C5    1    0.366866    0.429510    0.294018    11.00000    0.05464    0.06081 =
         0.04137   -0.00858   -0.00948    0.00888
AFIX  43
H5    2    0.367694    0.378630    0.214195    11.00000   -1.20000
AFIX   0
C6    1    0.423266    0.623810    0.335478    11.00000    0.04993    0.05574 =
         0.03911   -0.00259    0.00775    0.00275
AFIX  43
H6    2    0.462613    0.711260    0.283521    11.00000   -1.20000
AFIX   0
HKLF    4




REM  shelxt_a.res in Pca2(1)
REM wR2 = 0.0422, GooF = S = 0.871, Restrained GooF = 0.871 for all data
REM R1 = 0.0191 for 1538 Fo > 4sig(Fo) and 0.0232 for all 1695 data
REM 74 parameters refined using 1 restraints

END

WGHT      0.0212      0.0000

REM Highest difference peak  0.502,  deepest hole -0.478,  1-sigma level  0.089
Q1    1   0.4344  0.7197  0.7026  11.00000  0.05    0.50
Q2    1   0.6678  1.1388  0.5104  11.00000  0.05    0.37
Q3    1   0.3033  0.7416  0.7015  11.00000  0.05    0.36
Q4    1   0.3770  1.0395  0.7036  11.00000  0.05    0.36
Q5    1   0.5328  1.1215  0.5123  11.00000  0.05    0.29
Q6    1   0.6781  1.4104  0.5075  11.00000  0.05    0.28
Q7    1   0.5941  0.6613  0.5055  11.00000  0.05    0.28
Q8    1   0.3317  0.3028  0.7092  11.00000  0.05    0.28
Q9    1   0.4920  1.2002  0.5192  11.00000  0.05    0.27
Q10   1   0.5574  0.9133  0.2044  11.00000  0.05    0.26
Q11   1   0.2015  0.1096  0.5102  11.00000  0.05    0.26
Q12   1   0.2779  0.5093  0.7006  11.00000  0.05    0.25
Q13   1   0.3890  0.2869  0.4801  11.00000  0.05    0.25
Q14   1   0.5223  1.3868  0.5144  11.00000  0.05    0.25
Q15   1   0.7138  1.2572  0.4604  11.00000  0.05    0.25
Q16   1   0.2877  0.9496  0.7034  11.00000  0.05    0.24
Q17   1   0.3982  0.3214  0.2194  11.00000  0.05    0.24
Q18   1   0.3973  0.3211  0.5634  11.00000  0.05    0.23
Q19   1   0.3727  0.1989  0.1598  11.00000  0.05    0.23
Q20   1   0.1174  0.2487  0.3411  11.00000  0.05    0.23
;
_shelx_res_checksum              60330
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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 0.37539(3) 0.71174(10) 0.70663(5) 0.04761(15) Uani 1 1 d . . . . .
I2 I 0.59945(3) 1.12952(9) 0.50554(5) 0.04515(15) Uani 1 1 d . . . . .
C2 C 0.3666(4) 0.5822(14) 0.5289(6) 0.0392(14) Uani 1 1 d . . . . .
C3 C 0.3065(4) 0.3866(13) 0.4905(8) 0.0464(15) Uani 1 1 d . . . . .
H3 H 0.265636 0.308352 0.542887 0.056 Uiso 1 1 calc R U . . .
N1 N 0.4240(4) 0.6949(11) 0.4511(5) 0.0404(12) Uani 1 1 d . . . . .
H1 H 0.462392 0.815874 0.475862 0.048 Uiso 1 1 calc R U . . .
C4 C 0.3076(5) 0.3058(17) 0.3708(7) 0.0526(18) Uani 1 1 d . . . . .
H4 H 0.268328 0.168797 0.343432 0.063 Uiso 1 1 calc R U . . .
C5 C 0.3669(5) 0.4295(17) 0.2940(7) 0.0523(17) Uani 1 1 d . . . . .
H5 H 0.367694 0.378630 0.214195 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4233(5) 0.6238(16) 0.3355(6) 0.0483(17) Uani 1 1 d . . . . .
H6 H 0.462613 0.711260 0.283521 0.058 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0465(2) 0.0563(3) 0.0400(2) -0.0036(3) 0.0023(3) 0.0009(2)
I2 0.0486(2) 0.0457(2) 0.0412(2) 0.0023(2) -0.0017(2) -0.00545(18)
C2 0.035(3) 0.043(3) 0.039(4) 0.003(3) -0.002(3) 0.010(2)
C3 0.038(3) 0.052(3) 0.049(4) 0.002(4) -0.003(3) -0.004(3)
N1 0.038(3) 0.042(3) 0.041(3) -0.002(3) 0.000(2) 0.001(2)
C4 0.054(5) 0.051(4) 0.052(4) -0.001(3) -0.014(4) -0.005(3)
C5 0.055(4) 0.061(4) 0.041(3) -0.009(4) -0.009(3) 0.009(4)
C6 0.050(4) 0.056(4) 0.039(4) -0.003(3) 0.008(3) 0.003(3)
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'
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
N1 C2 C3 119.4(6) . . ?
N1 C2 I1 117.8(5) . . ?
C3 C2 I1 122.8(5) . . ?
C2 C3 C4 118.8(7) . . ?
C2 N1 C6 121.8(6) . . ?
C5 C4 C3 119.8(7) . . ?
C6 C5 C4 119.1(7) . . ?
C5 C6 N1 121.0(7) . . ?
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 2.096(6) . ?
C2 N1 1.342(9) . ?
C2 C3 1.364(9) . ?
C3 C4 1.400(12) . ?
N1 C6 1.343(9) . ?
C4 C5 1.374(12) . ?
C5 C6 1.336(11) . ?
