#------------------------------------------------------------------------------
#$Date: 2020-05-13 03:35:15 +0200 (Wed 13 de May de 2020) $
#$Revision: 252006 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/05/7240507.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_7240507
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      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                   14.9620(7)
_cell_length_b                   4.5454(2)
_cell_length_c                   10.9014(5)
_cell_measurement_reflns_used    2649
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.4733
_cell_measurement_theta_min      3.9724
_cell_volume                     741.39(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
;
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 0.993
_diffrn_measured_fraction_theta_max 0.994
_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  0.0414
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4389
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.993
_diffrn_reflns_theta_min         4.484
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    9.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28909
_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    2.561
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.139
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.11(3)
_refine_ls_extinction_coef       0.0354(16)
_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   0.880
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         1548
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      0.876
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0287
_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)+(0.0387P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0625
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                1228
_reflns_number_total             1548
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00534g2.cif
_cod_data_source_block           2-IPyHBr
_cod_database_code               7240507
_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 10:30:54 on 15-Oct-2019
CELL  0.71073  14.9620   4.5454  10.9014   90.000   90.000   90.000
ZERR     4.00   0.0007   0.0002   0.0005    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    BR   I
UNIT  20 20 4 4 4
MERG   2
OMIT    -4.00  54.00
omit 4 0 0
omit 0 0 4
omit 0 0 -4
TWIN
DELU     0.010   0.010 C4 C5
SIMU     0.040   0.080   1.700 C4 C5
DELU     0.010   0.010 C3 C6
SIMU     0.040   0.080   1.700 C3 C6
DELU     0.010   0.010 C2 C3 C6
SIMU     0.040   0.080   1.700 C2 C3 C6
FMAP   2
PLAN   20
ACTA
BOND
LIST   6
L.S.  30
WGHT    0.038700
EXTI    0.035393
BASF   0.11185
FVAR       4.54954
I1    5    0.621726    0.741327    0.714064    11.00000    0.04126    0.05055 =
         0.04149   -0.00353   -0.00316   -0.00018
BR1   4    0.401992    1.108095    0.505261    11.00000    0.05262    0.05817 =
         0.04159    0.00141    0.00175    0.01195
C2    1    0.631475    0.606493    0.530007    11.00000    0.02749    0.04005 =
         0.04423    0.00181   -0.00052   -0.00646
C3    1    0.695421    0.411207    0.491361    11.00000    0.03566    0.05644 =
         0.04969    0.00315    0.00290    0.00241
AFIX  43
H3    2    0.738029    0.338429    0.545556    11.00000   -1.20000
AFIX   0
N1    3    0.572342    0.714338    0.449513    11.00000    0.02930    0.04544 =
         0.04270   -0.00511   -0.00040   -0.00579
AFIX  43
H1    2    0.532477    0.836178    0.474988    11.00000   -1.20000
AFIX   0
C4    1    0.694853    0.324545    0.368466    11.00000    0.03554    0.06276 =
         0.06109   -0.00490    0.01348    0.00103
AFIX  43
H4    2    0.735712    0.185113    0.341022    11.00000   -1.20000
AFIX   0
C6    1    0.573087    0.639812    0.331780    11.00000    0.04348    0.05347 =
         0.04465    0.00020   -0.00748   -0.00658
AFIX  43
H6    2    0.531450    0.721784    0.278451    11.00000   -1.20000
AFIX   0
C5    1    0.634687    0.443234    0.288343    11.00000    0.05085    0.07371 =
         0.04542   -0.00830    0.01043   -0.01425
AFIX  43
H5    2    0.635560    0.391447    0.205820    11.00000   -1.20000
AFIX   0
HKLF    4




REM  shelxt_a.res in Pca2(1)
REM wR2 = 0.0625, GooF = S = 0.880, Restrained GooF = 0.876 for all data
REM R1 = 0.0287 for 1228 Fo > 4sig(Fo) and 0.0359 for all 1548 data
REM 75 parameters refined using 15 restraints

END

WGHT      0.0360      0.0000

REM Highest difference peak  0.538,  deepest hole -0.775,  1-sigma level  0.139
Q1    1   0.6193  0.5214  0.7132  11.00000  0.05    0.54
Q2    1   0.6184  0.9612  0.7264  11.00000  0.05    0.51
Q3    1   0.6180  0.8854  0.7716  11.00000  0.05    0.51
Q4    1   0.4047  1.2546  0.4428  11.00000  0.05    0.50
Q5    1   0.3992  0.8981  0.5036  11.00000  0.05    0.48
Q6    1   0.6217  0.6010  0.6389  11.00000  0.05    0.43
Q7    1   0.4069  1.3427  0.5122  11.00000  0.05    0.41
Q8    1   0.6213  0.6012  0.7828  11.00000  0.05    0.40
Q9    1   0.6614  0.2484  0.2197  11.00000  0.05    0.40
Q10   1   0.5887  0.8449  0.2346  11.00000  0.05    0.40
Q11   1   0.6373  0.4070  0.5053  11.00000  0.05    0.37
Q12   1   0.4725  0.9721  0.2973  11.00000  0.05    0.37
Q13   1   0.5955  0.6619  0.2074  11.00000  0.05    0.36
Q14   1   0.3995  1.0226  0.4278  11.00000  0.05    0.36
Q15   1   0.7797  0.1963  0.3886  11.00000  0.05    0.36
Q16   1   0.4110  0.9779  0.5869  11.00000  0.05    0.35
Q17   1   0.6113  0.7963  0.8612  11.00000  0.05    0.35
Q18   1   0.6217  0.2584  0.7156  11.00000  0.05    0.34
Q19   1   0.7927 -0.0065  0.3032  11.00000  0.05    0.33
Q20   1   0.7060  0.4834  0.6154  11.00000  0.05    0.33
;
_shelx_res_checksum              81695
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 0.62173(3) 0.74133(13) 0.71406(10) 0.0444(2) Uani 1 1 d . . . . .
Br1 Br 0.40199(6) 1.10810(18) 0.50526(11) 0.0508(3) Uani 1 1 d . . . . .
C2 C 0.6315(5) 0.6065(19) 0.5300(8) 0.037(2) Uani 1 1 d . U . . .
C3 C 0.6954(6) 0.4112(16) 0.4914(11) 0.047(2) Uani 1 1 d . U . . .
H3 H 0.738029 0.338429 0.545556 0.057 Uiso 1 1 calc R U . . .
N1 N 0.5723(5) 0.7143(14) 0.4495(7) 0.0391(17) Uani 1 1 d . . . . .
H1 H 0.532477 0.836178 0.474988 0.047 Uiso 1 1 calc R U . . .
C4 C 0.6949(7) 0.325(2) 0.3685(9) 0.053(2) Uani 1 1 d . U . . .
H4 H 0.735712 0.185113 0.341022 0.064 Uiso 1 1 calc R U . . .
C6 C 0.5731(7) 0.640(2) 0.3318(9) 0.047(2) Uani 1 1 d . . . . .
H6 H 0.531450 0.721784 0.278451 0.057 Uiso 1 1 calc R U . . .
C5 C 0.6347(7) 0.443(2) 0.2883(9) 0.057(3) Uani 1 1 d . U . . .
H5 H 0.635560 0.391447 0.205820 0.068 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 0.0413(3) 0.0506(3) 0.0415(3) -0.0035(3) -0.0032(3) -0.0002(3)
Br1 0.0526(5) 0.0582(5) 0.0416(4) 0.0014(6) 0.0018(6) 0.0119(4)
C2 0.027(4) 0.040(4) 0.044(6) 0.002(4) -0.001(3) -0.006(3)
C3 0.036(4) 0.056(5) 0.050(5) 0.003(5) 0.003(5) 0.002(4)
N1 0.029(4) 0.045(4) 0.043(4) -0.005(3) 0.000(3) -0.006(3)
C4 0.036(5) 0.063(6) 0.061(6) -0.005(4) 0.013(4) 0.001(4)
C6 0.043(6) 0.053(5) 0.045(5) 0.000(5) -0.007(4) -0.007(4)
C5 0.051(6) 0.074(7) 0.045(5) -0.008(5) 0.010(4) -0.014(5)
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
N1 C2 C3 119.8(8) . . ?
N1 C2 I1 118.2(6) . . ?
C3 C2 I1 122.0(7) . . ?
C2 C3 C4 118.2(9) . . ?
C6 N1 C2 122.3(8) . . ?
C5 C4 C3 120.4(9) . . ?
N1 C6 C5 120.5(9) . . ?
C4 C5 C6 118.7(10) . . ?
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 2.103(8) . ?
C2 N1 1.339(11) . ?
C2 C3 1.371(12) . ?
C3 C4 1.396(16) . ?
N1 C6 1.327(12) . ?
C4 C5 1.365(15) . ?
C6 C5 1.368(14) . ?
