#------------------------------------------------------------------------------
#$Date: 2020-05-13 04:35:15 +0300 (Wed, 13 May 2020) $
#$Revision: 252006 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240510.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_7240510
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_moiety         'C5 H5 I N, Br'
_chemical_formula_sum            'C5 H5 Br I N'
_chemical_formula_weight         285.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 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                 95.160(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.3789(3)
_cell_length_b                   8.5332(7)
_cell_length_c                   9.9405(6)
_cell_measurement_reflns_used    1476
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.4432
_cell_measurement_theta_min      4.0975
_cell_volume                     369.93(5)
_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      293(2)
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_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  0.0818
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1659
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         4.117
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    9.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15441
_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    2.567
_exptl_crystal_description       needle
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.574
_refine_diff_density_min         -2.093
_refine_diff_density_rms         0.291
_refine_ls_extinction_coef       0.101(11)
_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   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     30
_refine_ls_number_reflns         855
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0570
_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)+(0.1094P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.000
_reflns_number_gt                754
_reflns_number_total             855
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00534g2.cif
_cod_data_source_block           4-IPyHBr
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7240510
_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 P2(1)/m
    shelx.res
    created by SHELXL-2018/3 at 11:14:17 on 15-Oct-2019
CELL  0.71073   4.3789   8.5332   9.9405   90.000   95.160   90.000
ZERR     2.00   0.0003   0.0007   0.0006    0.000    0.006    0.000
LATT   1
SYMM  - X, 1/2 + Y, - Z
SFAC  C    H    N    BR   I
UNIT  10 10 2 2 2
MERG   2
OMIT    -4.00  54.00
OMIT     1   8   7
DELU     0.010   0.010 C3 C2
SIMU     0.040   0.080   1.700 C3 C2
DELU     0.010   0.010 C4 N1
SIMU     0.040   0.080   1.700 C4 N1
ISOR     0.100 C4 N1
EADP C3 C2
ISOR     0.050 C4 N1
FMAP   2
PLAN   20
ACTA
BOND
LIST   6
L.S.  40
WGHT    0.109400
EXTI    0.100528
FVAR       8.81049
I1    5    0.145045    0.750000    1.043435    10.50000    0.04454    0.04890 =
         0.03127    0.00000    0.00925    0.00000
BR1   4    0.979129    0.750000    0.366146    10.50000    0.05055    0.05539 =
         0.03227    0.00000    0.01345    0.00000
C4    1    0.323970    0.750000    0.853433    10.50000   10.03014   10.04941 =
        10.02240   10.00000    9.99247   10.00000
N1    3    0.603218    0.750000    0.625453    10.50000   10.04927   10.07263 =
        10.01895   10.00000    9.99316   10.00000
AFIX  43
H1    2    0.694822    0.749999    0.552469    10.50000   -1.20000
AFIX   0
C3    1    0.388273    0.612332    0.796074    11.00000    0.05770    0.04828 =
         0.03576   -0.00330    0.00349    0.00373
AFIX  43
H3    2    0.333964    0.518282    0.834751    11.00000   -1.20000
AFIX   0
C2    1    0.536674    0.612709    0.678473    11.00000    0.05770    0.04828 =
         0.03576   -0.00330    0.00349    0.00373
AFIX  43
H2    2    0.588131    0.519320    0.637892    11.00000   -1.20000
AFIX   0
HKLF    4




REM  shelxt_a.res in P2(1)/m
REM wR2 = 0.1573, GooF = S = 1.063, Restrained GooF = 1.052 for all data
REM R1 = 0.0570 for 754 Fo > 4sig(Fo) and 0.0611 for all 855 data
REM 30 parameters refined using 19 restraints

END

WGHT      0.1086      0.0000

REM Highest difference peak  1.574,  deepest hole -2.093,  1-sigma level  0.291
Q1    1   0.2148  0.7500  0.9227  10.50000  0.05    1.57
Q2    1   0.2199  0.8350  0.9964  11.00000  0.05    1.43
Q3    1   0.4011  0.7500  1.0159  10.50000  0.05    1.38
Q4    1  -0.1190  0.7500  1.0689  10.50000  0.05    1.34
Q5    1   0.0765  0.7500  1.1630  10.50000  0.05    1.09
Q6    1   0.8774  0.8407  0.4106  11.00000  0.05    1.01
Q7    1   0.0338  0.8563  1.0884  11.00000  0.05    0.89
Q8    1   1.2293  0.7500  0.3413  10.50000  0.05    0.88
Q9    1   1.0490  0.7500  0.2438  10.50000  0.05    0.86
Q10   1   1.0660  0.8472  0.3225  11.00000  0.05    0.81
Q11   1   0.9050  0.7500  0.4857  10.50000  0.05    0.81
Q12   1   0.1390  0.9005  1.0431  11.00000  0.05    0.76
Q13   1   0.2441  0.5737  0.9372  11.00000  0.05    0.69
Q14   1  -0.0474  0.7500  0.9472  10.50000  0.05    0.67
Q15   1   0.6644  0.7500  0.6649  10.50000  0.05    0.66
Q16   1   0.8671  0.9332  0.4716  11.00000  0.05    0.64
Q17   1   0.4610  0.7500  1.2207  10.50000  0.05    0.64
Q18   1   0.3309  0.7500  1.1458  10.50000  0.05    0.64
Q19   1  -0.1089  0.9554  0.9929  11.00000  0.05    0.61
Q20   1   0.7111  0.7500  0.3930  10.50000  0.05    0.60
;
_shelx_res_checksum              84094
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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 0.14504(14) 0.750000 1.04344(6) 0.0412(4) Uani 1 2 d S T P . .
Br1 Br 0.9791(3) 0.750000 0.36615(10) 0.0455(4) Uani 1 2 d S T P . .
C4 C 0.324(2) 0.750000 0.8534(9) 0.035 Uani 1 2 d S TU P . .
N1 N 0.603(2) 0.750000 0.6255(8) 0.048 Uani 1 2 d S TU P . .
H1 H 0.694822 0.749999 0.552469 0.057 Uiso 1 2 calc R U P . .
C3 C 0.3883(18) 0.6123(10) 0.7961(7) 0.0473(12) Uani 1 1 d . U . . .
H3 H 0.333964 0.518282 0.834751 0.057 Uiso 1 1 calc R U . . .
C2 C 0.5367(18) 0.6127(10) 0.6785(8) 0.0473(12) Uani 1 1 d . U . . .
H2 H 0.588131 0.519320 0.637892 0.057 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 0.0445(5) 0.0489(6) 0.0313(5) 0.000 0.0093(3) 0.000
Br1 0.0505(7) 0.0554(8) 0.0323(6) 0.000 0.0135(4) 0.000
C4 0.030 0.049 0.022 0.000 -0.008 0.000
N1 0.049 0.073 0.019 0.000 -0.007 0.000
C3 0.058(3) 0.048(3) 0.036(3) -0.003(2) 0.003(2) 0.004(2)
C2 0.058(3) 0.048(3) 0.036(3) -0.003(2) 0.003(2) 0.004(2)
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'
Br Br -0.2901 2.4595 '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
C3 C4 C3 121.5(10) 4_575 . ?
C3 C4 I1 119.2(5) 4_575 . ?
C3 C4 I1 119.2(5) . . ?
C2 N1 C2 123.9(10) 4_575 . ?
C4 C3 C2 119.1(9) . . ?
N1 C2 C3 118.2(8) . . ?
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 C4 2.109(10) . ?
C4 C3 1.347(9) 4_575 ?
C4 C3 1.347(9) . ?
N1 C2 1.328(9) 4_575 ?
N1 C2 1.328(9) . ?
C3 C2 1.388(11) . ?
