# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(2-IPyH)2ClI
_database_code_depnum_ccdc_archive 'CCDC 1995437'
loop_
_audit_author_name
_audit_author_address
'Vladimir Stilinovic'
;Department of Chemistry, Faculty of Science, University of Zagreb
Croatia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;
_vrf_PLAT434_ALERT_2_B           
; 
PROBLEM:   Short Inter HL..HL Contact I1       ..I3               3.43 Ang.

RESPONSE:  This short contact corresponds to the halogen bond between iodine atom(I1) and iodide anion(I3).
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Cl I3 N2'
_chemical_formula_weight         574.35

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.2027(6)
_cell_length_b                   8.8661(5)
_cell_length_c                   11.4800(7)
_cell_angle_alpha                89.566(5)
_cell_angle_beta                 70.547(6)
_cell_angle_gamma                81.668(6)
_cell_volume                     778.18(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2325
_cell_measurement_theta_min      3.7466
_cell_measurement_theta_max      37.4488

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.451
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    6.176
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            5878
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.765
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3374
_reflns_number_gt                2243
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_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_solution    
;
SHELXT (Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3374
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.921
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.53067(7) -0.01259(6) 0.26798(5) 0.05151(18) Uani 1 1 d . . . . .
I2 I 0.36212(7) 0.48172(6) 0.82512(5) 0.05355(18) Uani 1 1 d . . . . .
I3 I 0.29343(8) -0.21485(7) 0.14670(6) 0.0612(2) Uani 1 1 d . . . . .
Cl1 Cl 0.2269(3) 0.3473(2) 0.5222(2) 0.0590(5) Uani 1 1 d . . . . .
N1 N 0.6060(8) 0.2056(7) 0.4330(5) 0.0398(13) Uani 1 1 d . . . . .
H1 H 0.497611 0.238777 0.444900 0.048 Uiso 1 1 calc R U . . .
N2 N 0.0381(9) 0.5425(7) 0.7596(6) 0.0468(15) Uani 1 1 d . . . . .
H2 H 0.095430 0.471028 0.704962 0.056 Uiso 1 1 calc R U . . .
C1 C 0.6826(10) 0.0852(8) 0.3555(7) 0.0398(16) Uani 1 1 d . . . . .
C2 C 0.8547(11) 0.0339(9) 0.3307(7) 0.0483(19) Uani 1 1 d . . . . .
H2A H 0.911147 -0.047191 0.274040 0.058 Uiso 1 1 calc R U . . .
C10 C -0.1226(12) 0.5985(10) 0.7691(8) 0.056(2) Uani 1 1 d . . . . .
H10 H -0.172366 0.558930 0.716437 0.067 Uiso 1 1 calc R U . . .
C5 C 0.6851(11) 0.2751(9) 0.4911(7) 0.0489(19) Uani 1 1 d . . . . .
H5 H 0.626343 0.358429 0.544919 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1114(11) 0.5939(8) 0.8318(7) 0.0463(18) Uani 1 1 d . . . . .
C3 C 0.9416(11) 0.1016(10) 0.3889(8) 0.059(2) Uani 1 1 d . . . . .
H3 H 1.059598 0.066571 0.373683 0.071 Uiso 1 1 calc R U . . .
C9 C -0.2192(13) 0.7115(10) 0.8524(8) 0.063(2) Uani 1 1 d . . . . .
H9 H -0.333536 0.748388 0.857531 0.076 Uiso 1 1 calc R U . . .
C8 C -0.1494(13) 0.7670(11) 0.9246(8) 0.066(3) Uani 1 1 d . . . . .
H8 H -0.213555 0.846103 0.981317 0.079 Uiso 1 1 calc R U . . .
C4 C 0.8591(13) 0.2231(11) 0.4716(8) 0.062(2) Uani 1 1 d . . . . .
H4 H 0.919626 0.269165 0.513387 0.075 Uiso 1 1 calc R U . . .
C7 C 0.0222(13) 0.7098(9) 0.9188(7) 0.059(2) Uani 1 1 d . . . . .
H7 H 0.073136 0.748272 0.971252 0.071 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 0.0515(3) 0.0511(3) 0.0550(3) -0.0096(2) -0.0248(3) -0.0003(2)
I2 0.0417(3) 0.0606(3) 0.0577(3) -0.0075(2) -0.0197(3) 0.0023(2)
I3 0.0475(3) 0.0660(4) 0.0747(4) -0.0239(3) -0.0332(3) 0.0085(3)
Cl1 0.0360(10) 0.0696(13) 0.0705(14) -0.0265(10) -0.0209(10) 0.0036(10)
N1 0.031(3) 0.045(3) 0.043(3) -0.003(3) -0.014(3) -0.005(3)
N2 0.040(4) 0.053(4) 0.047(4) -0.003(3) -0.018(3) 0.002(3)
C1 0.042(4) 0.036(4) 0.044(4) 0.006(3) -0.018(3) -0.006(3)
C2 0.044(5) 0.044(4) 0.054(5) -0.007(3) -0.019(4) 0.007(4)
C10 0.050(5) 0.067(5) 0.054(5) 0.008(4) -0.026(4) -0.003(4)
C5 0.039(5) 0.052(5) 0.052(5) -0.015(4) -0.013(4) -0.003(4)
C6 0.043(5) 0.044(4) 0.046(4) 0.003(3) -0.011(4) 0.004(4)
C3 0.032(4) 0.069(6) 0.069(6) 0.017(5) -0.012(4) 0.003(4)
C9 0.049(5) 0.080(6) 0.057(5) 0.004(5) -0.021(5) 0.005(5)
C8 0.060(6) 0.077(6) 0.044(5) -0.004(4) -0.006(4) 0.019(5)
C4 0.058(6) 0.075(6) 0.066(6) 0.007(5) -0.028(5) -0.032(5)
C7 0.066(6) 0.058(5) 0.048(5) -0.018(4) -0.014(4) 0.001(5)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C1 2.115(7) . ?
I2 C6 2.128(8) . ?
N1 C5 1.287(9) . ?
N1 C1 1.333(9) . ?
N2 C6 1.294(10) . ?
N2 C10 1.308(10) . ?
C1 C2 1.352(11) . ?
C2 C3 1.327(11) . ?
C10 C9 1.351(12) . ?
C5 C4 1.377(12) . ?
C6 C7 1.378(11) . ?
C3 C4 1.377(13) . ?
C9 C8 1.288(12) . ?
C8 C7 1.405(13) . ?

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
C5 N1 C1 123.7(7) . . ?
C6 N2 C10 120.5(8) . . ?
N1 C1 C2 119.7(7) . . ?
N1 C1 I1 118.0(5) . . ?
C2 C1 I1 122.2(6) . . ?
C3 C2 C1 118.7(8) . . ?
N2 C10 C9 122.7(9) . . ?
N1 C5 C4 118.3(8) . . ?
N2 C6 C7 120.5(8) . . ?
N2 C6 I2 118.5(6) . . ?
C7 C6 I2 120.7(7) . . ?
C4 C3 C2 120.8(8) . . ?
C8 C9 C10 118.5(9) . . ?
C9 C8 C7 121.0(9) . . ?
C3 C4 C5 118.7(8) . . ?
C6 C7 C8 116.8(9) . . ?

_refine_diff_density_max         0.662
_refine_diff_density_min         -1.182
_refine_diff_density_rms         0.182

_shelx_res_file                  
;
TITL shelxt_a.res in P-1
    shelx.res
    created by SHELXL-2018/3 at 12:03:28 on 28-Jun-2019
CELL  0.71073   8.2027   8.8661  11.4800   89.566   70.547   81.668
ZERR     2.00   0.0006   0.0005   0.0007    0.005    0.006    0.006
LATT   1
SFAC  C    H    I    N    CL
UNIT  20 20 6 4 2
MERG   2
omit -4 54
acta
FMAP   2
PLAN   20
BOND
LIST   6
L.S.  10
WGHT    0.055400
FVAR       4.44899
I1    3    0.530668   -0.012590    0.267977    11.00000    0.05148    0.05114 =
         0.05502   -0.00956   -0.02485   -0.00027
I2    3    0.362121    0.481715    0.825122    11.00000    0.04171    0.06055 =
         0.05768   -0.00754   -0.01967    0.00231
I3    3    0.293430   -0.214847    0.146697    11.00000    0.04755    0.06598 =
         0.07472   -0.02390   -0.03320    0.00855
CL1   5    0.226889    0.347311    0.522200    11.00000    0.03598    0.06963 =
         0.07054   -0.02647   -0.02091    0.00365
N1    4    0.606007    0.205622    0.433002    11.00000    0.03128    0.04519 =
         0.04339   -0.00273   -0.01351   -0.00472
AFIX  43
H1    2    0.497611    0.238777    0.444900    11.00000   -1.20000
AFIX   0
N2    4    0.038100    0.542517    0.759610    11.00000    0.03996    0.05334 =
         0.04717   -0.00262   -0.01840    0.00191
AFIX  43
H2    2    0.095430    0.471028    0.704962    11.00000   -1.20000
AFIX   0
C1    1    0.682636    0.085151    0.355454    11.00000    0.04236    0.03619 =
         0.04377    0.00603   -0.01832   -0.00645
C2    1    0.854749    0.033923    0.330731    11.00000    0.04431    0.04402 =
         0.05407   -0.00731   -0.01860    0.00681
AFIX  43
H2A   2    0.911147   -0.047191    0.274040    11.00000   -1.20000
AFIX   0
C10   1   -0.122595    0.598503    0.769129    11.00000    0.05027    0.06706 =
         0.05418    0.00802   -0.02624   -0.00297
AFIX  43
H10   2   -0.172366    0.558930    0.716437    11.00000   -1.20000
AFIX   0
C5    1    0.685148    0.275143    0.491095    11.00000    0.03938    0.05250 =
         0.05240   -0.01451   -0.01343   -0.00285
AFIX  43
H5    2    0.626343    0.358429    0.544919    11.00000   -1.20000
AFIX   0
C6    1    0.111396    0.593931    0.831827    11.00000    0.04280    0.04351 =
         0.04607    0.00347   -0.01059    0.00352
C3    1    0.941599    0.101614    0.388912    11.00000    0.03159    0.06851 =
         0.06903    0.01682   -0.01162    0.00285
AFIX  43
H3    2    1.059598    0.066571    0.373683    11.00000   -1.20000
AFIX   0
C9    1   -0.219187    0.711488    0.852408    11.00000    0.04925    0.08009 =
         0.05743    0.00411   -0.02092    0.00545
AFIX  43
H9    2   -0.333536    0.748388    0.857531    11.00000   -1.20000
AFIX   0
C8    1   -0.149398    0.766990    0.924574    11.00000    0.06050    0.07650 =
         0.04365   -0.00425   -0.00571    0.01879
AFIX  43
H8    2   -0.213555    0.846103    0.981317    11.00000   -1.20000
AFIX   0
C4    1    0.859066    0.223105    0.471550    11.00000    0.05808    0.07548 =
         0.06592    0.00747   -0.02845   -0.03245
AFIX  43
H4    2    0.919626    0.269165    0.513387    11.00000   -1.20000
AFIX   0
C7    1    0.022202    0.709787    0.918839    11.00000    0.06565    0.05768 =
         0.04769   -0.01823   -0.01400    0.00149
AFIX  43
H7    2    0.073136    0.748272    0.971252    11.00000   -1.20000
AFIX   0
HKLF    4




REM  shelxt_a.res in P-1
REM wR2 = 0.1126, GooF = S = 0.921, Restrained GooF = 0.921 for all data
REM R1 = 0.0414 for 2243 Fo > 4sig(Fo) and 0.0647 for all 3374 data
REM 145 parameters refined using 0 restraints

END

WGHT      0.0562      0.0000

REM Highest difference peak  0.662,  deepest hole -1.182,  1-sigma level  0.182
Q1    1   0.4345  0.4340  0.5649  11.00000  0.05    0.66
Q2    1   0.5519  0.0752  0.2254  11.00000  0.05    0.66
Q3    1   0.2727 -0.0762  0.1388  11.00000  0.05    0.65
Q4    1   0.3148 -0.3045  0.1377  11.00000  0.05    0.63
Q5    1   0.4065 -0.0140  0.3649  11.00000  0.05    0.62
Q6    1   0.4140 -0.3317  0.0235  11.00000  0.05    0.61
Q7    1   0.6694  0.0838  0.3269  11.00000  0.05    0.61
Q8    1   0.1914 -0.2070  0.2274  11.00000  0.05    0.57
Q9    1   0.2359 -0.4047  0.1338  11.00000  0.05    0.57
Q10   1  -0.1383  0.5855  0.7346  11.00000  0.05    0.57
Q11   1   0.4916  0.0609  0.2950  11.00000  0.05    0.56
Q12   1  -0.1162  0.7791  0.9373  11.00000  0.05    0.55
Q13   1   0.4729  0.2772  0.5893  11.00000  0.05    0.54
Q14   1   0.4278 -0.2089  0.0433  11.00000  0.05    0.54
Q15   1  -0.2832  0.4686  0.7123  11.00000  0.05    0.54
Q16   1   0.4982  0.4396  0.4212  11.00000  0.05    0.51
Q17   1   0.3700  0.5841  0.8063  11.00000  0.05    0.51
Q18   1  -0.2628  0.7018  1.0681  11.00000  0.05    0.51
Q19   1   0.6757 -0.1223  0.3130  11.00000  0.05    0.51
Q20   1   0.9533  0.0868  0.4209  11.00000  0.05    0.50
;
_shelx_res_checksum              55896
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(3-IPyHCl)2H2O
_database_code_depnum_ccdc_archive 'CCDC 1995442'
loop_
_audit_author_name
_audit_author_address
'Vladimir Stilinovic'
;Department of Chemistry, Faculty of Science, University of Zagreb
Croatia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C5 H5 I N), 2(Cl), H2 O'
_chemical_formula_sum            'C10 H12 Cl2 I2 N2 O'
_chemical_formula_weight         500.92

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.0102(9)
_cell_length_b                   8.0918(10)
_cell_length_c                   14.0480(18)
_cell_angle_alpha                90.722(10)
_cell_angle_beta                 99.454(10)
_cell_angle_gamma                119.570(13)
_cell_volume                     776.53(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2711
_cell_measurement_theta_min      3.9134
_cell_measurement_theta_max      36.6148

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.142
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    4.381
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.39500
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            5112
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.919
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             3240
_reflns_number_gt                2434
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_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_solution    
;
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112-122.
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0100(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3240
_refine_ls_number_parameters     163
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.910
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I2 I 0.23662(4) 0.79351(4) 0.65869(2) 0.04190(12) Uani 1 1 d . . . . .
I1 I 0.95052(5) 0.76236(4) 0.90090(2) 0.04717(12) Uani 1 1 d . . . . .
Cl1 Cl 0.22896(19) 0.72741(17) 0.35228(8) 0.0512(3) Uani 1 1 d . . . . .
Cl2 Cl 0.57503(18) 0.7336(2) 0.77213(8) 0.0603(4) Uani 1 1 d . . . . .
O1 O 0.1809(7) 0.3376(6) 0.7763(3) 0.0699(10) Uani 1 1 d D . . . .
N1A N -0.2280(6) 0.9122(5) 0.5805(3) 0.0483(9) Uani 1 1 d . . . . .
H1A H -0.257677 0.990753 0.603967 0.058 Uiso 1 1 calc R U . . .
N1 N 1.3383(6) 0.7783(5) 1.1527(2) 0.0501(10) Uani 1 1 d . . . . .
H1 H 1.341424 0.788292 1.214079 0.060 Uiso 1 1 calc R U . . .
C5 C 1.4778(7) 0.7460(7) 1.0258(3) 0.0544(12) Uani 1 1 d . . . . .
H5 H 1.575673 0.735258 1.003693 0.065 Uiso 1 1 calc R U . . .
C5A C -0.3007(7) 0.6721(6) 0.4622(3) 0.0489(11) Uani 1 1 d . . . . .
H5A H -0.380497 0.589813 0.406614 0.059 Uiso 1 1 calc R U . . .
C2A C -0.0661(7) 0.9152(6) 0.6260(3) 0.0421(10) Uani 1 1 d . . . . .
H2A H 0.010697 0.999452 0.681398 0.051 Uiso 1 1 calc R U . . .
C4 C 1.3291(7) 0.7470(6) 0.9611(3) 0.0486(11) Uani 1 1 d . . . . .
H4 H 1.325884 0.735906 0.894723 0.058 Uiso 1 1 calc R U . . .
C6A C -0.3454(7) 0.7963(7) 0.5018(3) 0.0498(12) Uani 1 1 d . . . . .
H6A H -0.457257 0.799479 0.473833 0.060 Uiso 1 1 calc R U . . .
C2 C 1.1942(7) 0.7809(6) 1.0925(3) 0.0474(11) Uani 1 1 d . . . . .
H2 H 1.099695 0.793925 1.117014 0.057 Uiso 1 1 calc R U . . .
C6 C 1.4792(8) 0.7609(7) 1.1226(4) 0.0548(13) Uani 1 1 d . . . . .
H6 H 1.577398 0.758966 1.167391 0.066 Uiso 1 1 calc R U . . .
C3A C -0.0155(6) 0.7923(6) 0.5895(3) 0.0355(9) Uani 1 1 d . . . . .
C3 C 1.1838(7) 0.7646(6) 0.9944(3) 0.0416(10) Uani 1 1 d . . . . .
C4A C -0.1336(7) 0.6713(6) 0.5066(3) 0.0463(11) Uani 1 1 d . . . . .
H4A H -0.100455 0.588080 0.480171 0.056 Uiso 1 1 calc R U . . .
H7 H 0.290(6) 0.443(6) 0.768(4) 0.10(2) Uiso 1 1 d D . . . .
H8 H 0.094(9) 0.355(10) 0.727(4) 0.15(3) Uiso 1 1 d D . . . .

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
I2 0.03494(19) 0.04523(19) 0.04462(18) 0.00392(12) 0.00499(12) 0.02032(16)
I1 0.0416(2) 0.0506(2) 0.04760(19) 0.00607(13) 0.00611(14) 0.02267(17)
Cl1 0.0461(7) 0.0537(7) 0.0528(6) 0.0058(5) 0.0067(5) 0.0253(6)
Cl2 0.0400(8) 0.0908(10) 0.0546(7) 0.0156(6) 0.0098(6) 0.0360(8)
O1 0.052(3) 0.063(3) 0.089(3) 0.017(2) 0.002(2) 0.028(2)
N1A 0.049(3) 0.053(2) 0.057(2) 0.0124(18) 0.019(2) 0.034(2)
N1 0.057(3) 0.057(2) 0.0361(18) 0.0009(16) 0.0039(18) 0.030(2)
C5 0.041(3) 0.052(3) 0.072(3) 0.006(2) 0.018(2) 0.023(3)
C5A 0.034(3) 0.047(3) 0.049(2) 0.006(2) 0.003(2) 0.009(2)
C2A 0.041(3) 0.045(3) 0.040(2) 0.0036(18) 0.0074(19) 0.022(2)
C4 0.043(3) 0.051(3) 0.049(2) 0.007(2) 0.019(2) 0.019(3)
C6A 0.037(3) 0.061(3) 0.053(3) 0.024(2) 0.014(2) 0.025(3)
C2 0.049(3) 0.049(3) 0.049(2) 0.003(2) 0.013(2) 0.028(3)
C6 0.044(3) 0.054(3) 0.065(3) 0.003(2) -0.005(2) 0.028(3)
C3A 0.027(2) 0.039(2) 0.040(2) 0.0090(17) 0.0093(18) 0.015(2)
C3 0.039(3) 0.032(2) 0.044(2) 0.0013(18) 0.005(2) 0.012(2)
C4A 0.041(3) 0.040(2) 0.057(3) 0.006(2) 0.006(2) 0.020(2)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
I2 C3A 2.087(4) . ?
I1 C3 2.092(5) . ?
N1A C6A 1.322(5) . ?
N1A C2A 1.336(5) . ?
N1 C2 1.324(5) . ?
N1 C6 1.336(6) . ?
C5 C6 1.361(6) . ?
C5 C4 1.379(6) . ?
C5A C6A 1.362(6) . ?
C5A C4A 1.383(6) . ?
C2A C3A 1.367(5) . ?
C4 C3 1.390(6) . ?
C2 C3 1.369(6) . ?
C3A C4A 1.381(6) . ?

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
C6A N1A C2A 124.3(4) . . ?
C2 N1 C6 123.1(4) . . ?
C6 C5 C4 119.0(4) . . ?
C6A C5A C4A 118.5(4) . . ?
N1A C2A C3A 118.8(4) . . ?
C5 C4 C3 120.4(4) . . ?
N1A C6A C5A 119.2(4) . . ?
N1 C2 C3 120.1(4) . . ?
N1 C6 C5 119.5(4) . . ?
C2A C3A C4A 118.3(4) . . ?
C2A C3A I2 119.8(3) . . ?
C4A C3A I2 121.9(3) . . ?
C2 C3 C4 117.9(4) . . ?
C2 C3 I1 119.3(4) . . ?
C4 C3 I1 122.8(3) . . ?
C3A C4A C5A 121.0(4) . . ?

_refine_diff_density_max         0.817
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.107

_shelx_res_file                  
;
TITL OPTI_TRIKLINSKI in P-1
    shelx.res
    created by SHELXL-2018/3 at 14:10:18 on 15-Oct-2019
CELL  0.71073   8.0102   8.0918  14.0480   90.722   99.454  119.570
ZERR     2.00   0.0009   0.0010   0.0018    0.010    0.010    0.013
LATT   1
SFAC  C    H    N    CL   I    O
UNIT  20 24 4 4 4 2
MERG   2
OMIT    -4.00  54.00
OMIT    -1   1   3
OMIT     0   2   0
OMIT    -1  -1   3
OMIT     1  -1   2
DFIX  0.96 0.04 O1 H7 O1 H8
dang   1.5   0.08   H7 H8
DELU     0.010   0.010 CL1 CL2 O1
SIMU     0.040   0.080   1.700 CL1 CL2 O1
FMAP   2
PLAN   20
ACTA
L.S.  50
WGHT    0.031700
EXTI    0.010046
FVAR       4.61435
I2    5    0.236616    0.793510    0.658690    11.00000    0.03494    0.04523 =
         0.04462    0.00392    0.00499    0.02032
I1    5    0.950516    0.762359    0.900901    11.00000    0.04163    0.05061 =
         0.04760    0.00607    0.00611    0.02267
CL1   4    0.228964    0.727407    0.352278    11.00000    0.04611    0.05370 =
         0.05279    0.00583    0.00667    0.02526
CL2   4    0.575033    0.733583    0.772130    11.00000    0.04003    0.09082 =
         0.05457    0.01558    0.00976    0.03597
O1    6    0.180900    0.337563    0.776336    11.00000    0.05209    0.06327 =
         0.08883    0.01734    0.00232    0.02801
N1A   3   -0.227955    0.912169    0.580503    11.00000    0.04943    0.05337 =
         0.05699    0.01244    0.01916    0.03418
AFIX  43
H1A   2   -0.257677    0.990753    0.603967    11.00000   -1.20000
AFIX   0
N1    3    1.338317    0.778311    1.152710    11.00000    0.05660    0.05738 =
         0.03609    0.00087    0.00394    0.02998
AFIX  43
H1    2    1.341424    0.788292    1.214079    11.00000   -1.20000
AFIX   0
C5    1    1.477808    0.745977    1.025800    11.00000    0.04110    0.05247 =
         0.07224    0.00602    0.01850    0.02328
AFIX  43
H5    2    1.575673    0.735258    1.003693    11.00000   -1.20000
AFIX   0
C5A   1   -0.300656    0.672131    0.462203    11.00000    0.03410    0.04716 =
         0.04882    0.00634    0.00284    0.00947
AFIX  43
H5A   2   -0.380497    0.589813    0.406614    11.00000   -1.20000
AFIX   0
C2A   1   -0.066131    0.915221    0.625965    11.00000    0.04106    0.04511 =
         0.04020    0.00356    0.00736    0.02193
AFIX  43
H2A   2    0.010697    0.999452    0.681398    11.00000   -1.20000
AFIX   0
C4    1    1.329070    0.747013    0.961056    11.00000    0.04341    0.05145 =
         0.04877    0.00740    0.01868    0.01943
AFIX  43
H4    2    1.325884    0.735906    0.894723    11.00000   -1.20000
AFIX   0
C6A   1   -0.345443    0.796256    0.501794    11.00000    0.03707    0.06150 =
         0.05308    0.02447    0.01411    0.02459
AFIX  43
H6A   2   -0.457257    0.799479    0.473833    11.00000   -1.20000
AFIX   0
C2    1    1.194154    0.780934    1.092533    11.00000    0.04937    0.04930 =
         0.04907    0.00297    0.01302    0.02798
AFIX  43
H2    2    1.099695    0.793925    1.117014    11.00000   -1.20000
AFIX   0
C6    1    1.479181    0.760891    1.122595    11.00000    0.04443    0.05351 =
         0.06496    0.00289   -0.00518    0.02832
AFIX  43
H6    2    1.577398    0.758966    1.167391    11.00000   -1.20000
AFIX   0
C3A   1   -0.015474    0.792286    0.589536    11.00000    0.02702    0.03869 =
         0.03993    0.00905    0.00934    0.01492
C3    1    1.183825    0.764564    0.994350    11.00000    0.03882    0.03220 =
         0.04442    0.00128    0.00536    0.01183
C4A   1   -0.133639    0.671321    0.506588    11.00000    0.04110    0.03974 =
         0.05669    0.00598    0.00624    0.02026
AFIX  43
H4A   2   -0.100455    0.588080    0.480171    11.00000   -1.20000
AFIX   0
H7    2    0.290286    0.442842    0.767630    11.00000    0.09712
H8    2    0.093672    0.355315    0.727227    11.00000    0.15286
HKLF    4




REM  OPTI_TRIKLINSKI in P-1
REM wR2 = 0.0678, GooF = S = 0.910, Restrained GooF = 0.910 for all data
REM R1 = 0.0297 for 2434 Fo > 4sig(Fo) and 0.0426 for all 3240 data
REM 163 parameters refined using 3 restraints

END

WGHT      0.0317      0.0000

REM Highest difference peak  0.817,  deepest hole -0.840,  1-sigma level  0.107
Q1    1   0.9974  0.6978  0.8820  11.00000  0.05    0.82
Q2    1   0.2955  0.7181  0.6463  11.00000  0.05    0.60
Q3    1   0.2084  0.8615  0.6813  11.00000  0.05    0.56
Q4    1   0.2935  0.7496  0.7203  11.00000  0.05    0.54
Q5    1   0.1759  0.8309  0.5893  11.00000  0.05    0.53
Q6    1  -0.4664  0.8286  0.4208  11.00000  0.05    0.51
Q7    1   0.2462  0.7560  0.5743  11.00000  0.05    0.50
Q8    1   0.8590  0.8363  0.8987  11.00000  0.05    0.49
Q9    1   0.9783  0.7438  0.8142  11.00000  0.05    0.46
Q10   1   0.2411  0.8530  0.7529  11.00000  0.05    0.44
Q11   1   0.8807  0.7898  0.8340  11.00000  0.05    0.44
Q12   1   1.0160  0.7210  0.9620  11.00000  0.05    0.43
Q13   1   1.6556  0.7275  1.1495  11.00000  0.05    0.39
Q14   1  -0.1856  0.3774  0.4563  11.00000  0.05    0.38
Q15   1   0.9418  0.7793  0.9745  11.00000  0.05    0.37
Q16   1   0.4734  0.8815  0.7492  11.00000  0.05    0.34
Q17   1   0.5850  0.6412  0.7706  11.00000  0.05    0.34
Q18   1  -0.1835  0.7217  0.4832  11.00000  0.05    0.33
Q19   1   1.0263  0.8997  0.8568  11.00000  0.05    0.31
Q20   1   0.7386  0.5786  0.8889  11.00000  0.05    0.31
;
_shelx_res_checksum              79194
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3-IPyHBr
_database_code_depnum_ccdc_archive 'CCDC 1995443'
loop_
_audit_author_name
_audit_author_address
'Vladimir Stilinovic'
;Department of Chemistry, Faculty of Science, University of Zagreb
Croatia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H5 I N, Br'
_chemical_formula_sum            'C5 H5 Br I N'
_chemical_formula_weight         285.91

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.5838(2)
_cell_length_b                   14.8642(5)
_cell_length_c                   10.6931(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.693(3)
_cell_angle_gamma                90
_cell_volume                     728.25(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3351
_cell_measurement_theta_min      3.8139
_cell_measurement_theta_max      36.5721

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.608
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    9.782
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30647
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            8044
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.052
_diffrn_reflns_theta_max         26.981
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1565
_reflns_number_gt                1151
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_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_solution    
;
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1565
_refine_ls_number_parameters     73
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0625
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_restrained_S_all      0.892
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.73156(7) 0.37211(2) -0.07312(3) 0.04676(13) Uani 1 1 d . . . . .
Br1 Br 0.92493(11) 0.10998(3) 0.12602(4) 0.04760(15) Uani 1 1 d . . . . .
N1 N 0.6423(8) 0.4389(3) 0.3124(3) 0.0501(10) Uani 1 1 d . . . . .
H1 H 0.722126 0.478022 0.361775 0.060 Uiso 1 1 calc R U . . .
C5 C 0.3216(9) 0.3185(4) 0.2815(4) 0.0493(12) Uani 1 1 d . U . . .
H5 H 0.182211 0.279423 0.312098 0.059 Uiso 1 1 calc R U . . .
C3 C 0.6049(9) 0.3730(3) 0.1134(4) 0.0370(10) Uani 1 1 d . U . . .
C4 C 0.4051(10) 0.3118(3) 0.1594(4) 0.0455(11) Uani 1 1 d . U . . .
H4 H 0.328502 0.266627 0.107934 0.055 Uiso 1 1 calc R U . . .
C2 C 0.7208(9) 0.4364(3) 0.1937(4) 0.0443(11) Uani 1 1 d . U . . .
H2 H 0.855097 0.477902 0.164942 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4440(11) 0.3827(4) 0.3578(5) 0.0537(13) Uani 1 1 d . U . . .
H6 H 0.389770 0.387324 0.440657 0.064 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 0.0550(2) 0.0467(2) 0.03879(17) -0.00303(14) 0.00401(13) -0.00319(14)
Br1 0.0542(3) 0.0498(3) 0.0389(2) 0.0022(2) 0.0032(2) 0.0013(2)
N1 0.057(3) 0.054(3) 0.040(2) -0.011(2) -0.0013(19) 0.001(2)
C5 0.043(3) 0.048(3) 0.057(3) 0.012(2) 0.008(2) -0.001(2)
C3 0.042(3) 0.033(2) 0.036(2) 0.0039(18) -0.0007(18) 0.0033(18)
C4 0.050(3) 0.040(3) 0.047(2) 0.001(2) -0.003(2) 0.000(2)
C2 0.047(3) 0.042(3) 0.044(2) 0.001(2) 0.004(2) 0.001(2)
C6 0.059(3) 0.063(4) 0.039(2) 0.007(2) 0.007(2) 0.009(2)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C3 2.093(4) . ?
N1 C2 1.331(5) . ?
N1 C6 1.336(6) . ?
C5 C6 1.365(7) . ?
C5 C4 1.376(6) . ?
C3 C2 1.372(6) . ?
C3 C4 1.391(6) . ?

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
C2 N1 C6 122.4(4) . . ?
C6 C5 C4 119.8(4) . . ?
C2 C3 C4 118.4(4) . . ?
C2 C3 I1 119.2(3) . . ?
C4 C3 I1 122.5(3) . . ?
C5 C4 C3 119.5(4) . . ?
N1 C2 C3 120.4(4) . . ?
N1 C6 C5 119.5(4) . . ?

_refine_diff_density_max         0.838
_refine_diff_density_min         -1.093
_refine_diff_density_rms         0.123

_shelx_res_file                  
;
TITL PRELIM in P2(1)/c
    shelx.res
    created by SHELXL-2018/3 at 10:45:10 on 15-Oct-2019
CELL  0.71073   4.5838  14.8642  10.6931   90.000   91.693   90.000
ZERR     4.00   0.0002   0.0005   0.0003    0.000    0.003    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    BR   I
UNIT  20 20 4 4 4
MERG   2
OMIT    -4.00  54.00
OMIT     0   0   2
OMIT     0   4   0
DELU     0.010   0.010 C5 C4 C2 C6 c3
SIMU     0.040   0.080   1.700 C5 C4 C2 C6 c3
FMAP   2
PLAN   25
ACTA
L.S.  50
WGHT    0.036200
FVAR       3.75219
I1    5    0.731556    0.372110   -0.073118    11.00000    0.05496    0.04669 =
         0.03879   -0.00303    0.00401   -0.00319
BR1   4    0.924928    0.109984    0.126022    11.00000    0.05418    0.04983 =
         0.03889    0.00216    0.00323    0.00126
N1    3    0.642318    0.438860    0.312437    11.00000    0.05651    0.05366 =
         0.04011   -0.01066   -0.00132    0.00129
AFIX  43
H1    2    0.722126    0.478022    0.361775    11.00000   -1.20000
AFIX   0
C5    1    0.321626    0.318502    0.281544    11.00000    0.04314    0.04809 =
         0.05719    0.01220    0.00812   -0.00069
AFIX  43
H5    2    0.182211    0.279423    0.312098    11.00000   -1.20000
AFIX   0
C3    1    0.604878    0.372961    0.113362    11.00000    0.04239    0.03277 =
         0.03566    0.00385   -0.00066    0.00334
C4    1    0.405103    0.311773    0.159388    11.00000    0.04964    0.03987 =
         0.04665    0.00077   -0.00306   -0.00011
AFIX  43
H4    2    0.328502    0.266627    0.107934    11.00000   -1.20000
AFIX   0
C2    1    0.720847    0.436393    0.193666    11.00000    0.04728    0.04216 =
         0.04364    0.00120    0.00439    0.00060
AFIX  43
H2    2    0.855097    0.477902    0.164942    11.00000   -1.20000
AFIX   0
C6    1    0.444027    0.382711    0.357783    11.00000    0.05939    0.06282 =
         0.03915    0.00678    0.00715    0.00931
AFIX  43
H6    2    0.389770    0.387324    0.440657    11.00000   -1.20000
AFIX   0
HKLF    4




REM  PRELIM in P2(1)/c
REM wR2 = 0.0651, GooF = S = 0.900, Restrained GooF = 0.892 for all data
REM R1 = 0.0290 for 1151 Fo > 4sig(Fo) and 0.0442 for all 1565 data
REM 73 parameters refined using 31 restraints

END

WGHT      0.0358      0.0000

REM Highest difference peak  0.838,  deepest hole -1.093,  1-sigma level  0.123
Q1    1   0.7321  0.4301 -0.0704  11.00000  0.05    0.84
Q2    1   0.5977  0.3717  0.0001  11.00000  0.05    0.61
Q3    1   0.7384  0.3116 -0.0641  11.00000  0.05    0.52
Q4    1   0.7564  0.1116  0.2007  11.00000  0.05    0.41
Q5    1   0.4112  0.3719 -0.1731  11.00000  0.05    0.40
Q6    1   0.6255  0.3914  0.5109  11.00000  0.05    0.38
Q7    1   0.6866  0.2057  0.2454  11.00000  0.05    0.37
Q8    1   0.8382  0.1191  0.2134  11.00000  0.05    0.36
Q9    1   0.6587  0.5611  0.2156  11.00000  0.05    0.35
Q10   1   0.8243  0.3742 -0.1512  11.00000  0.05    0.35
Q11   1   0.9342  0.1681  0.1326  11.00000  0.05    0.34
Q12   1   0.1669  0.3895  0.1162  11.00000  0.05    0.34
Q13   1   0.0937  0.3806  0.4652  11.00000  0.05    0.34
Q14   1   0.3012  0.4498  0.0162  11.00000  0.05    0.34
Q15   1   0.8459  0.5751  0.0186  11.00000  0.05    0.33
Q16   1   0.7339  0.0506  0.2531  11.00000  0.05    0.33
Q17   1   1.0960  0.3674 -0.1350  11.00000  0.05    0.32
Q18   1   0.3000  0.3773  0.5845  11.00000  0.05    0.32
Q19   1   0.7895  0.2464 -0.1040  11.00000  0.05    0.31
Q20   1   0.3202  0.3796  0.3112  11.00000  0.05    0.31
Q21   1   0.8463  0.5477  0.1613  11.00000  0.05    0.30
Q22   1   0.8307  0.3726  0.2180  11.00000  0.05    0.30
Q23   1   0.9264  0.0520  0.1345  11.00000  0.05    0.30
Q24   1   0.5852  0.3394  0.1243  11.00000  0.05    0.30
Q25   1   1.1943  0.1129  0.1835  11.00000  0.05    0.30
;
_shelx_res_checksum              13737
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4-IPyHI
_database_code_depnum_ccdc_archive 'CCDC 1995447'
loop_
_audit_author_name
_audit_author_address
'Vladimir Stilinovic'
;Department of Chemistry, Faculty of Science, University of Zagreb
Croatia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H5 I N, I'
_chemical_formula_sum            'C5 H5 I2 N'
_chemical_formula_weight         332.90

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.57920(10)
_cell_length_b                   21.7962(6)
_cell_length_c                   8.1293(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.885(3)
_cell_angle_gamma                90
_cell_volume                     793.99(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5056
_cell_measurement_theta_min      3.7306
_cell_measurement_theta_max      36.2588

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.785
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.36
_exptl_absorpt_coefficient_mu    7.829
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40369
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            12719
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.739
_diffrn_reflns_theta_max         26.957
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1717
_reflns_number_gt                1241
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_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_solution    
;
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112-122.
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1717
_refine_ls_number_parameters     61
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0618
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_restrained_S_all      0.896
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I2 I -0.44803(8) 0.18289(2) 1.23061(5) 0.04858(13) Uani 1 1 d . . . . .
I1 I 0.29451(9) -0.02395(2) 0.74396(5) 0.05097(13) Uani 1 1 d . . . . .
N1 N 0.0105(10) 0.1885(2) 0.7236(6) 0.0528(12) Uani 1 1 d . U . . .
H1 H -0.046657 0.226140 0.718482 0.063 Uiso 1 1 calc R U . . .
C3 C 0.2422(12) 0.1076(2) 0.6139(7) 0.0505(10) Uani 1 1 d . U . . .
H3 H 0.342877 0.092204 0.534426 0.061 Uiso 1 1 calc R U . . .
C2 C 0.1590(13) 0.1676(2) 0.6086(7) 0.0500(9) Uani 1 1 d . U . . .
H2 H 0.204120 0.193674 0.526806 0.060 Uiso 1 1 calc R U . . .
C6 C -0.0516(12) 0.1527(2) 0.8460(8) 0.0500(9) Uani 1 1 d . U . . .
H6 H -0.147247 0.169225 0.926228 0.060 Uiso 1 1 calc R U . . .
C5 C 0.0248(12) 0.0923(2) 0.8531(7) 0.0505(10) Uani 1 1 d . U . . .
H5 H -0.024767 0.066778 0.934888 0.061 Uiso 1 1 calc R U . . .
C4 C 0.1776(11) 0.0697(2) 0.7364(6) 0.0400(12) Uani 1 1 d . . . . .

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
I2 0.0486(2) 0.0392(2) 0.0600(3) 0.00257(18) 0.01590(18) 0.00015(15)
I1 0.0602(2) 0.0395(2) 0.0537(3) -0.00027(17) 0.01294(18) 0.00452(16)
N1 0.059(3) 0.038(2) 0.056(3) -0.005(2) 0.001(2) 0.005(2)
C3 0.057(2) 0.049(2) 0.049(3) -0.0006(19) 0.020(2) 0.0007(18)
C2 0.055(2) 0.048(2) 0.048(3) -0.0052(18) 0.0133(19) -0.0039(18)
C6 0.055(2) 0.048(2) 0.048(3) -0.0052(18) 0.0133(19) -0.0039(18)
C5 0.057(2) 0.049(2) 0.049(3) -0.0006(19) 0.020(2) 0.0007(18)
C4 0.044(3) 0.036(3) 0.038(3) -0.002(2) 0.004(2) -0.002(2)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 2.108(5) . ?
N1 C6 1.339(7) . ?
N1 C2 1.344(7) . ?
N1 H1 0.8600 . ?
C3 C2 1.361(7) . ?
C3 C4 1.371(7) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C6 C5 1.361(7) . ?
C6 H6 0.9300 . ?
C5 C4 1.381(7) . ?
C5 H5 0.9300 . ?

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 122.3(5) . . ?
C6 N1 H1 118.8 . . ?
C2 N1 H1 118.8 . . ?
C2 C3 C4 120.0(5) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
N1 C2 C3 118.8(5) . . ?
N1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
N1 C6 C5 120.2(5) . . ?
N1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C5 C4 118.5(5) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 I1 120.8(4) . . ?
C5 C4 I1 119.1(4) . . ?

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 1.8(8) . . . . ?
C4 C3 C2 N1 -0.8(8) . . . . ?
C2 N1 C6 C5 -2.8(9) . . . . ?
N1 C6 C5 C4 2.7(8) . . . . ?
C2 C3 C4 C5 0.8(8) . . . . ?
C2 C3 C4 I1 178.5(4) . . . . ?
C6 C5 C4 C3 -1.7(8) . . . . ?
C6 C5 C4 I1 -179.4(4) . . . . ?

_refine_diff_density_max         0.808
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.130

_shelx_res_file                  
;
TITL SIR92 run in space group P 1 21/c 1
    shelx.res
    created by SHELXL-2018/3 at 11:56:09 on 15-Oct-2019
CELL  0.71073   4.5792  21.7962   8.1293   90.000  101.885   90.000
ZERR     4.00   0.0001   0.0006   0.0003    0.000    0.003    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    I
UNIT  20 20 4 8
MERG   2
OMIT    -4.00  54.00
OMIT     1   2   0
OMIT     1   1   0
OMIT     1   0   0
OMIT     0   4   1
OMIT    -1   7   3
DELU     0.010   0.010 N1 C3 C2 C6 C5
SIMU     0.040   0.080   1.700 N1 C3 C2 C6 C5
EADP C2 C6
EADP C3 C5
FMAP   2
PLAN   25
ACTA
BOND   $H
CONF
L.S.  40
TEMP    25.00
WGHT    0.034200
FVAR       2.55040
I2    4   -0.448027    0.182894    1.230613    11.00000    0.04865    0.03918 =
         0.05995    0.00257    0.01590    0.00015
I1    4    0.294514   -0.023950    0.743957    11.00000    0.06023    0.03947 =
         0.05373   -0.00027    0.01294    0.00452
N1    3    0.010504    0.188479    0.723610    11.00000    0.05933    0.03820 =
         0.05598   -0.00537    0.00053    0.00486
AFIX  43
H1    2   -0.046657    0.226140    0.718482    11.00000   -1.20000
AFIX   0
C3    1    0.242182    0.107565    0.613906    11.00000    0.05692    0.04925 =
         0.04941   -0.00063    0.02022    0.00075
AFIX  43
H3    2    0.342877    0.092204    0.534426    11.00000   -1.20000
AFIX   0
C2    1    0.159004    0.167576    0.608595    11.00000    0.05509    0.04784 =
         0.04834   -0.00516    0.01327   -0.00389
AFIX  43
H2    2    0.204120    0.193674    0.526806    11.00000   -1.20000
AFIX   0
C6    1   -0.051603    0.152714    0.845954    11.00000    0.05509    0.04784 =
         0.04834   -0.00516    0.01327   -0.00389
AFIX  43
H6    2   -0.147247    0.169225    0.926228    11.00000   -1.20000
AFIX   0
C5    1    0.024825    0.092301    0.853134    11.00000    0.05692    0.04925 =
         0.04941   -0.00063    0.02022    0.00075
AFIX  43
H5    2   -0.024767    0.066778    0.934888    11.00000   -1.20000
AFIX   0
C4    1    0.177649    0.069723    0.736352    11.00000    0.04435    0.03639 =
         0.03758   -0.00202    0.00446   -0.00192
HKLF    4




REM  SIR92 run in space group P 1 21/c 1
REM wR2 = 0.0618, GooF = S = 0.903, Restrained GooF = 0.896 for all data
REM R1 = 0.0281 for 1241 Fo > 4sig(Fo) and 0.0450 for all 1717 data
REM 61 parameters refined using 31 restraints

END

WGHT      0.0347      0.0000

REM Highest difference peak  0.808,  deepest hole -0.610,  1-sigma level  0.130
Q1    1   0.2677  0.0210  0.7578  11.00000  0.05    0.81
Q2    1  -0.4527  0.1383  1.2148  11.00000  0.05    0.77
Q3    1   0.3260 -0.0635  0.7673  11.00000  0.05    0.72
Q4    1  -0.4369  0.2268  1.2198  11.00000  0.05    0.67
Q5    1   0.3069 -0.0037  0.6529  11.00000  0.05    0.57
Q6    1  -0.1879 -0.0218  0.7316  11.00000  0.05    0.54
Q7    1  -0.7013  0.1111  1.2493  11.00000  0.05    0.53
Q8    1  -0.2940  0.1597  0.7422  11.00000  0.05    0.52
Q9    1   0.2663 -0.0330  0.8839  11.00000  0.05    0.47
Q10   1  -0.5523  0.2672  1.2660  11.00000  0.05    0.47
Q11   1   0.4598  0.1335  0.7618  11.00000  0.05    0.47
Q12   1  -0.4465  0.2101  1.3239  11.00000  0.05    0.45
Q13   1   0.0420  0.3151  0.7497  11.00000  0.05    0.44
Q14   1   0.1957 -0.0232  0.8334  11.00000  0.05    0.44
Q15   1  -0.0914  0.1804  1.2550  11.00000  0.05    0.44
Q16   1   0.2632 -0.0516  0.6399  11.00000  0.05    0.43
Q17   1  -0.1006  0.1124  0.8269  11.00000  0.05    0.40
Q18   1   0.0892  0.2271  0.7269  11.00000  0.05    0.40
Q19   1   0.0979  0.1284  0.9036  11.00000  0.05    0.38
Q20   1  -0.4985  0.1830  1.3396  11.00000  0.05    0.37
Q21   1  -0.0037  0.1777  0.8252  11.00000  0.05    0.36
Q22   1   0.1324  0.1790  0.6706  11.00000  0.05    0.36
Q23   1  -0.3721  0.1757  1.1407  11.00000  0.05    0.35
Q24   1   0.6130 -0.0285  0.7579  11.00000  0.05    0.34
Q25   1  -0.0587  0.1310  0.7564  11.00000  0.05    0.34
;
_shelx_res_checksum              29730
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2-IPyHCl
_database_code_depnum_ccdc_archive 'CCDC 1995438'
loop_
_audit_author_name
_audit_author_address
'Vladimir Stilinovic'
;Department of Chemistry, Faculty of Science, University of Zagreb
Croatia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H5 Cl I N'
_chemical_formula_weight         241.45

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   4.4564(3)
_cell_length_b                   10.8438(7)
_cell_length_c                   14.8824(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.886(7)
_cell_angle_gamma                90
_cell_volume                     716.57(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1443
_cell_measurement_theta_min      3.9931
_cell_measurement_theta_max      38.2095

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.238
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    4.738
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.13277
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            5186
_diffrn_reflns_av_unetI/netI     0.1139
_diffrn_reflns_av_R_equivalents  0.1385
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.002
_diffrn_reflns_theta_max         26.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1550
_reflns_number_gt                883
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_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_solution    
;
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112-122.
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0155P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1550
_refine_ls_number_parameters     73
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   0.800
_refine_ls_restrained_S_all      0.797
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_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 0.0629(3) 0.0564(3) 0.0538(3) -0.0017(2) -0.0143(2) 0.0005(3)
Cl1 0.0827(14) 0.0592(13) 0.0634(11) 0.0009(10) -0.0273(9) -0.0020(11)
N1 0.063(4) 0.061(4) 0.040(3) 0.001(3) -0.015(3) -0.001(3)
C4 0.114(7) 0.056(5) 0.067(5) -0.002(4) -0.029(4) -0.012(5)
C2 0.056(4) 0.049(5) 0.047(4) 0.009(3) -0.002(3) 0.014(4)
C3 0.067(5) 0.066(6) 0.058(4) -0.001(4) -0.022(4) 0.002(4)
C6 0.087(6) 0.064(6) 0.050(5) 0.006(4) -0.009(4) 0.008(4)
C5 0.098(6) 0.065(5) 0.077(5) -0.003(5) -0.013(4) -0.020(5)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_refine_diff_density_max         0.885
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.131

_shelx_res_file                  
;
TITL SIR92 run in space group P 21/n
    shelx.res
    created by SHELXL-2018/3 at 14:31:49 on 15-Oct-2019
CELL  0.71073   4.4564  10.8438  14.8824   90.000   94.886   90.000
ZERR     4.00   0.0003   0.0007   0.0011    0.000    0.007    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    CL   I
UNIT  20 20 4 4 4
MERG   2
OMIT    -4.00  54.00
OMIT    -1   0   3
OMIT     0   0  10
OMIT     2   1  15
OMIT     3   1   0
OMIT    -1   0   9
OMIT     1   1  12
SIMU     0.040   0.080   1.700 C4 C3 C6 C5
DELU     0.010   0.010 C6 C5
DELU     0.010   0.010 C4 C5

FMAP   2
PLAN   25
ACTA
BOND   $H
CONF
L.S.  50
TEMP    25.00
WGHT    0.015500
FVAR       3.13228
I1    5    0.553983   -0.037344    0.857874    11.00000    0.06294    0.05637 =
         0.05383   -0.00166   -0.01432    0.00055
CL1   4    0.064563    0.181388    0.672682    11.00000    0.08267    0.05920 =
         0.06341    0.00092   -0.02735   -0.00196
N1    3    0.520375    0.235174    0.828092    11.00000    0.06311    0.06054 =
         0.04011    0.00146   -0.01467   -0.00103
AFIX  43
H1    2    0.393098    0.212828    0.784445    11.00000   -1.20000
AFIX   0
C4    1    0.911249    0.307344    0.965241    11.00000    0.11449    0.05592 =
         0.06699   -0.00202   -0.02871   -0.01223
AFIX  43
H4    2    1.039500    0.332536    1.014381    11.00000   -1.20000
AFIX   0
C2    1    0.659747    0.147432    0.881965    11.00000    0.05590    0.04940 =
         0.04723    0.00898   -0.00243    0.01408
C3    1    0.857771    0.184529    0.951089    11.00000    0.06668    0.06569 =
         0.05801   -0.00143   -0.02181    0.00232
AFIX  43
H3    2    0.956890    0.126375    0.988760    11.00000   -1.20000
AFIX   0
C6    1    0.575095    0.353231    0.840982    11.00000    0.08749    0.06418 =
         0.05002    0.00593   -0.00909    0.00790
AFIX  43
H6    2    0.472219    0.410461    0.803372    11.00000   -1.20000
AFIX   0
C5    1    0.777609    0.393902    0.907671    11.00000    0.09836    0.06550 =
         0.07710   -0.00286   -0.01258   -0.01997
AFIX  43
H5    2    0.824030    0.477222    0.914107    11.00000   -1.20000
AFIX   0
HKLF    4




REM  SIR92 run in space group P 21/n
REM wR2 = 0.0836, GooF = S = 0.800, Restrained GooF = 0.797 for all data
REM R1 = 0.0413 for 883 Fo > 4sig(Fo) and 0.0883 for all 1550 data
REM 73 parameters refined using 20 restraints

END

WGHT      0.0155      0.0000

REM Highest difference peak  0.885,  deepest hole -0.653,  1-sigma level  0.131
Q1    1   0.4546 -0.0346  0.7971  11.00000  0.05    0.89
Q2    1   0.6659 -0.0374  0.9167  11.00000  0.05    0.83
Q3    1   0.5466 -0.1254  0.8610  11.00000  0.05    0.69
Q4    1   0.5489  0.0662  0.8605  11.00000  0.05    0.59
Q5    1   0.2195 -0.0409  0.8827  11.00000  0.05    0.58
Q6    1   0.3164 -0.0369  0.9429  11.00000  0.05    0.51
Q7    1   0.0519  0.2738  0.6780  11.00000  0.05    0.50
Q8    1   1.2430  0.1382  1.0401  11.00000  0.05    0.39
Q9    1   0.6159 -0.0378  0.8485  11.00000  0.05    0.38
Q10   1   0.8915 -0.0339  0.8387  11.00000  0.05    0.36
Q11   1   0.2667  0.1924  0.6387  11.00000  0.05    0.36
Q12   1   1.0105 -0.0351  0.8423  11.00000  0.05    0.35
Q13   1   0.9422  0.3998  0.8006  11.00000  0.05    0.35
Q14   1   0.7272  0.2096  0.9621  11.00000  0.05    0.35
Q15   1   0.4857  0.1314  0.8197  11.00000  0.05    0.33
Q16   1   0.7032  0.0150  0.9847  11.00000  0.05    0.33
Q17   1   0.6661  0.2109  0.8771  11.00000  0.05    0.31
Q18   1   0.3949  0.5319  0.8798  11.00000  0.05    0.31
Q19   1   0.1557  0.3352  0.7729  11.00000  0.05    0.31
Q20   1  -0.1124  0.1828  0.6011  11.00000  0.05    0.30
Q21   1   0.4062  0.0057  0.7410  11.00000  0.05    0.30
Q22   1   0.6996  0.5417  0.8545  11.00000  0.05    0.30
Q23   1   0.4028  0.1661  0.9635  11.00000  0.05    0.30
Q24   1   0.1851  0.3732  0.7402  11.00000  0.05    0.30
Q25   1   0.6060  0.4591  0.7248  11.00000  0.05    0.30
;
_shelx_res_checksum              5861
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3-IPyHI
_database_code_depnum_ccdc_archive 'CCDC 1995444'
loop_
_audit_author_name
_audit_author_address
'Vladimir Stilinovic'
;Department of Chemistry, Faculty of Science, University of Zagreb
Croatia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H5 I2 N'
_chemical_formula_weight         332.90

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.6289(2)
_cell_length_b                   15.1319(8)
_cell_length_c                   11.0844(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.478(7)
_cell_angle_gamma                90
_cell_volume                     776.14(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4568
_cell_measurement_theta_min      4.0291
_cell_measurement_theta_max      37.3831

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.849
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.27
_exptl_absorpt_coefficient_mu    8.009
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36106
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            4872
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.404
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1683
_reflns_number_gt                1524
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_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_solution    
;
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790
;
_computing_structure_refinement  
;
Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0558P)²+0.2022P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0061(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1683
_refine_ls_number_parameters     78
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.924
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.40203(6) 0.38874(2) 0.12615(2) 0.02038(14) Uani 1 1 d . . . . .
I2 I 0.22339(6) 0.37461(2) 0.43196(3) 0.02278(14) Uani 1 1 d . . . . .
C4 C -0.1005(9) 0.3121(3) 0.6541(4) 0.0221(9) Uani 1 1 d . . . . .
H4 H -0.178364 0.269470 0.602276 0.027 Uiso 1 1 calc R U . . .
C5 C -0.1830(9) 0.3156(3) 0.7737(4) 0.0262(10) Uani 1 1 d . . . . .
H5 H -0.317633 0.275657 0.802411 0.031 Uiso 1 1 calc R U . . .
C3 C 0.0991(9) 0.3728(3) 0.6124(4) 0.0178(9) Uani 1 1 d . . . . .
C2 C 0.2130(9) 0.4346(3) 0.6922(4) 0.0202(9) Uani 1 1 d . . . . .
H2 H 0.345368 0.476231 0.665993 0.024 Uiso 1 1 calc R U . . .
N1 N 0.1317(8) 0.4345(3) 0.8075(4) 0.0248(8) Uani 1 1 d . . . . .
C6 C -0.0636(10) 0.3787(3) 0.8494(5) 0.0263(10) Uani 1 1 d . . . . .
H6 H -0.119202 0.382243 0.929329 0.032 Uiso 1 1 calc R U . . .
H1 H 0.213(10) 0.468(4) 0.852(5) 0.026(14) Uiso 1 1 d . . . . .

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 0.0264(2) 0.01857(19) 0.0164(2) -0.00054(11) 0.00369(12) 0.00000(9)
I2 0.0318(2) 0.0205(2) 0.0162(2) -0.00111(11) 0.00504(13) -0.00269(10)
C4 0.027(2) 0.018(2) 0.022(2) -0.0021(19) -0.0003(18) 0.0002(16)
C5 0.030(2) 0.026(2) 0.023(2) 0.008(2) 0.006(2) -0.0001(17)
C3 0.022(2) 0.019(2) 0.013(2) 0.0023(17) 0.0023(16) 0.0045(15)
C2 0.028(2) 0.014(2) 0.018(2) -0.0014(19) 0.0028(17) 0.0017(16)
N1 0.033(2) 0.025(2) 0.0164(19) -0.0059(18) 0.0003(16) -0.0009(16)
C6 0.029(2) 0.031(3) 0.019(2) 0.003(2) 0.0001(19) 0.0035(18)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
I2 C3 2.095(5) . ?
C4 C3 1.390(6) . ?
C4 C5 1.391(6) . ?
C5 C6 1.377(7) . ?
C3 C2 1.383(6) . ?
C2 N1 1.341(6) . ?
N1 C6 1.330(6) . ?

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 C5 119.6(4) . . ?
C6 C5 C4 119.5(4) . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 I2 121.8(3) . . ?
C2 C3 I2 119.5(3) . . ?
N1 C2 C3 119.7(4) . . ?
C6 N1 C2 123.0(4) . . ?
N1 C6 C5 119.5(5) . . ?

_refine_diff_density_max         1.228
_refine_diff_density_min         -1.566
_refine_diff_density_rms         0.198

_shelx_res_file                  
;
TITL PRELIM 2 in P2(1)/c
    shelx.res
    created by SHELXL-2018/3 at 14:16:31 on 27-Jun-2019
CELL  0.71073   4.6289  15.1319  11.0844   90.000   91.478   90.000
ZERR     4.00   0.0002   0.0008   0.0009    0.000    0.007    0.000
LATT   1
SYMM  - X, 1/2 + 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
L.S.  10
WGHT    0.055800    0.202200
EXTI    0.006127
FVAR       3.46504
I1    4    0.402031    0.388738    0.126147    11.00000    0.02636    0.01857 =
         0.01637   -0.00054    0.00369    0.00000
I2    4    0.223386    0.374609    0.431959    11.00000    0.03181    0.02054 =
         0.01621   -0.00111    0.00504   -0.00269
C4    1   -0.100490    0.312106    0.654055    11.00000    0.02682    0.01780 =
         0.02171   -0.00210   -0.00031    0.00024
AFIX  43
H4    2   -0.178364    0.269470    0.602276    11.00000   -1.20000
AFIX   0
C5    1   -0.182982    0.315594    0.773743    11.00000    0.03008    0.02555 =
         0.02332    0.00833    0.00571   -0.00006
AFIX  43
H5    2   -0.317633    0.275657    0.802411    11.00000   -1.20000
AFIX   0
C3    1    0.099091    0.372763    0.612369    11.00000    0.02197    0.01877 =
         0.01285    0.00233    0.00225    0.00454
C2    1    0.212971    0.434647    0.692168    11.00000    0.02839    0.01413 =
         0.01821   -0.00145    0.00284    0.00165
AFIX  43
H2    2    0.345368    0.476231    0.665993    11.00000   -1.20000
AFIX   0
N1    3    0.131716    0.434454    0.807459    11.00000    0.03291    0.02516 =
         0.01643   -0.00590    0.00026   -0.00087
C6    1   -0.063613    0.378679    0.849446    11.00000    0.02868    0.03139 =
         0.01892    0.00310    0.00013    0.00351
AFIX  43
H6    2   -0.119202    0.382243    0.929329    11.00000   -1.20000
AFIX   0
H1    2    0.213241    0.467927    0.852343    11.00000    0.02642
HKLF    4




REM  PRELIM 2 in P2(1)/c
REM wR2 = 0.0803, GooF = S = 0.924, Restrained GooF = 0.924 for all data
REM R1 = 0.0310 for 1524 Fo > 4sig(Fo) and 0.0347 for all 1683 data
REM 78 parameters refined using 0 restraints

END

WGHT      0.0402      0.0000

REM Highest difference peak  1.228,  deepest hole -1.566,  1-sigma level  0.198
Q1    1   0.3038  0.4307  0.1052  11.00000  0.05    1.23
Q2    1   0.2998  0.3880  0.2007  11.00000  0.05    1.17
Q3    1   0.5095  0.3901  0.0519  11.00000  0.05    1.09
Q4    1   0.1323  0.3737  0.5148  11.00000  0.05    1.07
Q5    1   0.4868  0.4356  0.1511  11.00000  0.05    0.99
Q6    1   0.1403  0.4187  0.4198  11.00000  0.05    0.96
Q7    1   0.3066  0.3475  0.1073  11.00000  0.05    0.93
Q8    1   0.3276  0.3336  0.4579  11.00000  0.05    0.92
Q9    1   0.1450  0.3318  0.4132  11.00000  0.05    0.90
Q10   1   0.2914  0.3739  0.3600  11.00000  0.05    0.89
Q11   1   0.6415  0.3904  0.1214  11.00000  0.05    0.76
Q12   1   0.2330  0.4159  0.4427  11.00000  0.05    0.74
Q13   1  -0.2902  0.3851  1.0052  11.00000  0.05    0.70
Q14   1   0.1633  0.3929  0.1343  11.00000  0.05    0.70
Q15   1   0.4965  0.3428  0.1544  11.00000  0.05    0.62
Q16   1   0.3628  0.2990  0.3815  11.00000  0.05    0.59
Q17   1   0.1881  0.4328  0.7544  11.00000  0.05    0.57
Q18   1   0.3534  0.4493  0.3810  11.00000  0.05    0.55
Q19   1  -0.1534  0.3795  0.5619  11.00000  0.05    0.54
Q20   1   0.4475  0.3712  0.4311  11.00000  0.05    0.54
;
_shelx_res_checksum              87365
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2-IPyHI
_database_code_depnum_ccdc_archive 'CCDC 1995440'
loop_
_audit_author_name
_audit_author_address
'Vladimir Stilinovic'
;Department of Chemistry, Faculty of Science, University of Zagreb
Croatia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_vrf_PLAT434_ALERT_2_B           
; 
PROBLEM:   Short Inter HL..HL Contact I1       ..I2               3.47 Ang.  

RESPONSE:  This short contact corresponds to the halogen bond between iodine atom(I1) and iodide anion(I2).
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H5 I2 N'
_chemical_formula_weight         332.90

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   15.0849(7)
_cell_length_b                   4.7247(2)
_cell_length_c                   11.2538(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     802.08(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4246
_cell_measurement_theta_min      3.8616
_cell_measurement_theta_max      36.2759

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.757
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    7.750
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60257
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            6146
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.314
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             1695
_reflns_number_gt                1538
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_max     0.947
_reflns_Friedel_fraction_full    0.943

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_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_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0261(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_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)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1695
_refine_ls_number_parameters     74
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0191
_refine_ls_wR_factor_ref         0.0422
_refine_ls_wR_factor_gt          0.0413
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_restrained_S_all      0.871
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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) . ?

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) . . ?

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.089

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2-IPyHBr
_database_code_depnum_ccdc_archive 'CCDC 1995439'
loop_
_audit_author_name
_audit_author_address
'Vladimir Stilinovic'
;Department of Chemistry, Faculty of Science, University of Zagreb
Croatia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H5 I N, Br'
_chemical_formula_sum            'C5 H5 Br I N'
_chemical_formula_weight         285.91

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   14.9620(7)
_cell_length_b                   4.5454(2)
_cell_length_c                   10.9014(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     741.39(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2649
_cell_measurement_theta_min      3.9724
_cell_measurement_theta_max      36.4733

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.561
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    9.609
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.28909
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            4389
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.484
_diffrn_reflns_theta_max         26.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             1548
_reflns_number_gt                1228
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_max     0.921
_reflns_Friedel_fraction_full    0.922

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_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_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_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_solution    
;
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112-122.
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0354(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.11(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1548
_refine_ls_number_parameters     75
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0625
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_restrained_S_all      0.876
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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) . ?

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) . . ?

_refine_diff_density_max         0.538
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.139

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4-IPyHCl
_database_code_depnum_ccdc_archive 'CCDC 1995445'
loop_
_audit_author_name
_audit_author_address
'Vladimir Stilinovic'
;Department of Chemistry, Faculty of Science, University of Zagreb
Croatia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_vrf_PLAT930_ALERT_2_B           
; 
PROBLEM:   CF-based   Twin Law ( 0 0 1)[ 1 0 5] Est.d BASF       0.18 Check   

RESPONSE:  The proposed Twin Law was checked and and did not help to improve the model. 
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H5 I N, Cl'
_chemical_formula_sum            'C5 H5 Cl I N'
_chemical_formula_weight         241.45

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_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, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   4.3369(8)
_cell_length_b                   8.4079(17)
_cell_length_c                   9.736(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.120(18)
_cell_angle_gamma                90
_cell_volume                     354.10(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    899
_cell_measurement_theta_min      4.1998
_cell_measurement_theta_max      32.7105

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.265
_exptl_crystal_F_000             224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    4.794
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.11855
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            1860
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.197
_diffrn_reflns_theta_max         26.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             810
_reflns_number_gt                605
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_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_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_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_solution    
;
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112-122.
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1306P)²+2.4460P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         810
_refine_ls_number_parameters     44
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0811
_refine_ls_wR_factor_ref         0.2298
_refine_ls_wR_factor_gt          0.2208
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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 0.1423(3) 0.750000 0.54323(13) 0.0498(6) Uani 1 2 d S T P . .
Cl1 Cl -0.0130(13) 0.750000 0.8647(5) 0.0529(13) Uani 1 2 d S T P . .
C4 C 0.34924(3) 0.750000 0.35373(2) 0.042(4) Uani 1 2 d DS TU P . .
N1 N 0.629(4) 0.750000 0.1170(18) 0.056(5) Uani 1 2 d S TU P . .
H1 H 0.729148 0.749999 0.043976 0.068 Uiso 1 2 calc R U P . .
C3 C 0.39425(9) 0.60810(2) 0.28832(2) 0.055(3) Uani 1 1 d D U . . .
H3 H 0.318960 0.513317 0.322041 0.067 Uiso 1 1 calc R U . . .
C2 C 0.55446(4) 0.61049(2) 0.17115(2) 0.061(4) Uani 1 1 d D U . . .
H2 H 0.610255 0.515843 0.130169 0.073 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 0.0475(8) 0.0515(9) 0.0518(9) 0.000 0.0124(6) 0.000
Cl1 0.059(3) 0.058(3) 0.044(3) 0.000 0.022(2) 0.000
C4 0.047(10) 0.041(9) 0.040(9) 0.000 0.017(8) 0.000
N1 0.047(9) 0.086(14) 0.038(9) 0.000 0.011(7) 0.000
C3 0.070(9) 0.038(8) 0.058(8) -0.001(6) 0.000(7) -0.011(7)
C2 0.076(10) 0.055(10) 0.051(7) -0.007(7) 0.003(7) 0.004(8)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 2.1090(13) . ?
C4 C3 1.3730(2) . ?
C4 C3 1.3730(2) 4_575 ?
N1 C2 1.335(8) 4_575 ?
N1 C2 1.335(8) . ?
C3 C2 1.3778(3) . ?

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 120.682(19) . 4_575 ?
C3 C4 I1 119.305(11) . . ?
C3 C4 I1 119.304(11) 4_575 . ?
C2 N1 C2 123.0(13) 4_575 . ?
C4 C3 C2 117.925(15) . . ?
N1 C2 C3 119.4(6) . . ?

_refine_diff_density_max         3.451
_refine_diff_density_min         -1.548
_refine_diff_density_rms         0.292

_shelx_res_file                  
;
TITL shelxt_a.res in P2(1)/m
    shelx.res
    created by SHELXL-2018/3 at 13:54:35 on 15-Oct-2019
CELL  0.71073   4.3369   8.4079   9.7361   90.000   94.120   90.000
ZERR     2.00   0.0008   0.0017   0.0020    0.000    0.018    0.000
LATT   1
SYMM  - X, 1/2 + Y, - Z
SFAC  C    H    N    CL   I
UNIT  10 10 2 2 2
MERG   2
OMIT    -4.00  54.00
OMIT     3   2   3
OMIT     3   1   1
OMIT     3   3   1
OMIT    -3   2   3
OMIT    -3   0   3
OMIT    -3   4   3
OMIT     3   3   2
TWIN   -1.00  0.00  0.00  0.00 -1.00  0.00  0.32  0.00  1.00   2
DELU     0.010   0.010 C3 C2
SIMU     0.040   0.080   1.700 C3 C2
ISOR     0.100 C4 N1
DFIX     1.373   0.0000020 C4 C3
DANG     2.357   0.0000020 C4 C2
FMAP   2
PLAN   20
ACTA
BOND
LIST   6
L.S.  40
WGHT    0.130600    2.446000
BASF   0.00136
FVAR       7.05278
I1    5    0.142276    0.750000    0.543234    10.50000    0.04753    0.05152 =
         0.05175    0.00000    0.01243    0.00000
CL1   4   -0.013018    0.750000    0.864680    10.50000    0.05942    0.05783 =
         0.04421    0.00000    0.02186    0.00000
C4    1    0.349235    0.750000    0.353731    10.50000    0.04712    0.04050 =
         0.04019    0.00000    0.01686    0.00000
N1    3    0.628809    0.750000    0.117021    10.50000    0.04679    0.08588 =
         0.03773    0.00000    0.01131    0.00000
AFIX  43
H1    2    0.729148    0.749999    0.043976    10.50000   -1.20000
AFIX   0
C3    1    0.394254    0.608096    0.288315    11.00000    0.07012    0.03797 =
         0.05762   -0.00089    0.00035   -0.01100
AFIX  43
H3    2    0.318960    0.513317    0.322041    11.00000   -1.20000
AFIX   0
C2    1    0.554462    0.610493    0.171146    11.00000    0.07594    0.05518 =
         0.05105   -0.00691    0.00311    0.00443
AFIX  43
H2    2    0.610255    0.515843    0.130169    11.00000   -1.20000
AFIX   0
HKLF    4




REM  shelxt_a.res in P2(1)/m
REM wR2 = 0.2298, GooF = S = 1.089, Restrained GooF = 1.075 for all data
REM R1 = 0.0811 for 605 Fo > 4sig(Fo) and 0.0968 for all 810 data
REM 44 parameters refined using 21 restraints

END

WGHT      0.1307      2.5141

REM Highest difference peak  3.451,  deepest hole -1.548,  1-sigma level  0.292
Q1    1   0.4827  0.7500  0.5503  10.50000  0.05    3.45
Q2    1  -0.1800  0.7500  0.5412  10.50000  0.05    3.41
Q3    1   0.0884  0.7500  0.3773  10.50000  0.05    1.51
Q4    1   0.2712  0.8374  0.5995  11.00000  0.05    1.26
Q5    1  -0.0127  0.8222  0.4804  11.00000  0.05    1.09
Q6    1   0.7528  0.7500  0.3746  10.50000  0.05    1.05
Q7    1   0.1058  0.7500  0.9366  10.50000  0.05    0.93
Q8    1   0.3504  0.7500  0.4404  10.50000  0.05    0.92
Q9    1   0.8338  0.7500  0.0328  10.50000  0.05    0.86
Q10   1   0.1861  0.7500  1.0387  10.50000  0.05    0.84
Q11   1   0.3715  0.7500  0.8854  10.50000  0.05    0.74
Q12   1  -0.1233  0.7500  0.8432  10.50000  0.05    0.73
Q13   1  -0.2956  0.7500  0.8680  10.50000  0.05    0.66
Q14   1  -0.2645  0.7500  0.7482  10.50000  0.05    0.64
Q15   1   0.0230  0.7978  0.7478  11.00000  0.05    0.62
Q16   1   0.1572  0.8341  0.6483  11.00000  0.05    0.60
Q17   1   0.5078  0.7500  0.2382  10.50000  0.05    0.59
Q18   1   0.1862  0.7500  0.2149  10.50000  0.05    0.58
Q19   1   0.5178  0.7500  0.0281  10.50000  0.05    0.55
Q20   1  -0.0632  0.7500  0.6599  10.50000  0.05    0.53
;
_shelx_res_checksum              87647
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3-IPyHCl
_database_code_depnum_ccdc_archive 'CCDC 1995441'
loop_
_audit_author_name
_audit_author_address
'Vladimir Stilinovic'
;Department of Chemistry, Faculty of Science, University of Zagreb
Croatia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H5 Cl I N'
_chemical_formula_weight         241.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_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, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   10.5864(11)
_cell_length_b                   4.3468(5)
_cell_length_c                   15.0822(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.518(8)
_cell_angle_gamma                90
_cell_volume                     694.01(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1271
_cell_measurement_theta_min      4.1050
_cell_measurement_theta_max      69.9210

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.311
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   0.472
_exptl_transmission_factor_max   2.564
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    38.942
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            2838
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.176
_diffrn_reflns_theta_max         76.418
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             1423
_reflns_number_gt                1244
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0892P)²+0.4203P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1423
_refine_ls_number_parameters     73
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1498
_refine_ls_wR_factor_gt          0.1370
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 1.3119(7) -0.1794(18) 0.6887(5) 0.0503(16) Uani 1 1 d . . . . .
H1 H 1.336121 -0.305248 0.729451 0.060 Uiso 1 1 calc R U . . .
C3 C 1.1479(6) 0.091(2) 0.6185(5) 0.0432(16) Uani 1 1 d . . . . .
C4 C 1.2326(8) 0.202(2) 0.5571(6) 0.0467(18) Uani 1 1 d . . . . .
H4 H 1.205224 0.324056 0.509961 0.056 Uiso 1 1 calc R U . . .
C5 C 1.3616(7) 0.127(3) 0.5677(6) 0.056(2) Uani 1 1 d . U . . .
H5 H 1.421214 0.210010 0.529689 0.067 Uiso 1 1 calc R U . . .
C2 C 1.1902(7) -0.107(2) 0.6844(5) 0.0441(16) Uani 1 1 d . . . . .
H2 H 1.133935 -0.188410 0.725138 0.053 Uiso 1 1 calc R U . . .
C6 C 1.3986(8) -0.069(3) 0.6339(6) 0.058(2) Uani 1 1 d . . . . .
H6 H 1.483084 -0.123953 0.640544 0.070 Uiso 1 1 calc R U . . .
I1 I 0.95719(4) 0.22115(13) 0.61807(3) 0.0455(3) Uani 1 1 d . . . . .
Cl1 Cl 1.33469(17) -1.4170(6) 0.35207(14) 0.0530(5) Uani 1 1 d . . . . .

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
N1 0.052(4) 0.050(4) 0.049(4) 0.001(3) -0.010(3) 0.008(3)
C3 0.027(3) 0.055(5) 0.047(3) -0.001(3) 0.001(2) 0.007(3)
C4 0.047(4) 0.051(5) 0.042(4) 0.002(3) 0.001(3) 0.004(3)
C5 0.030(3) 0.072(5) 0.066(4) -0.002(4) 0.012(3) 0.001(4)
C2 0.040(3) 0.048(4) 0.044(4) -0.002(3) -0.003(3) 0.003(3)
C6 0.044(4) 0.069(6) 0.062(5) -0.005(5) 0.002(3) 0.014(4)
I1 0.0379(3) 0.0542(4) 0.0443(4) 0.00265(19) -0.0013(2) 0.00539(18)
Cl1 0.0400(8) 0.0565(13) 0.0625(11) -0.0031(9) -0.0021(7) 0.0024(8)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 C2 1.326(11) . ?
N1 C6 1.331(13) . ?
C3 C4 1.383(11) . ?
C3 C2 1.385(12) . ?
C3 I1 2.097(6) . ?
C4 C5 1.413(12) . ?
C5 C6 1.366(15) . ?

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
C2 N1 C6 124.0(8) . . ?
C4 C3 C2 119.4(7) . . ?
C4 C3 I1 122.2(6) . . ?
C2 C3 I1 118.4(5) . . ?
C3 C4 C5 118.3(8) . . ?
C6 C5 C4 119.9(8) . . ?
N1 C2 C3 119.4(7) . . ?
N1 C6 C5 118.9(8) . . ?

_refine_diff_density_max         1.530
_refine_diff_density_min         -1.333
_refine_diff_density_rms         0.219

_shelx_res_file                  
;
TITL SIR92 run in space group P 2/c
    shelx.res
    created by SHELXL-2018/3 at 10:25:43 on 04-Mar-2020
CELL  1.54184  10.5864   4.3468  15.0822   90.000   90.518   90.000
ZERR   4.00   0.0011   0.0005   0.0014    0.000    0.008    0.000
LATT   1
SYMM  - X,   Y, 1/2 - Z
SFAC  C    H    N    CL   I
UNIT  20  20  4  4  4
MERG   2
OMIT    -4.00 180.00
OMIT    12   1   3
OMIT    13   0   0
OMIT   -10   1  11
ISOR    0.010  0.20  C5
FMAP   2
PLAN   20
ACTA
BOND
L.S.  34
TEMP    25.00
WGHT    0.089200    0.420300
FVAR       3.84189
N1    3    1.311855   -0.179377    0.688735    11.00000    0.05173    0.04977 =
         0.04926    0.00135   -0.00987    0.00832
AFIX  43
H1    2    1.336121   -0.305248    0.729451    11.00000   -1.20000
AFIX   0
C3    1    1.147919    0.090696    0.618525    11.00000    0.02738    0.05522 =
         0.04714   -0.00104    0.00082    0.00689
C4    1    1.232550    0.202328    0.557077    11.00000    0.04682    0.05091 =
         0.04247    0.00223    0.00100    0.00425
AFIX  43
H4    2    1.205224    0.324056    0.509961    11.00000   -1.20000
AFIX   0
C5    1    1.361575    0.126733    0.567703    11.00000    0.02996    0.07168 =
         0.06642   -0.00213    0.01162    0.00079
AFIX  43
H5    2    1.421214    0.210010    0.529689    11.00000   -1.20000
AFIX   0
C2    1    1.190243   -0.107085    0.684374    11.00000    0.04045    0.04765 =
         0.04422   -0.00223   -0.00262    0.00305
AFIX  43
H2    2    1.133935   -0.188410    0.725138    11.00000   -1.20000
AFIX   0
C6    1    1.398638   -0.068892    0.633900    11.00000    0.04400    0.06881 =
         0.06161   -0.00483    0.00176    0.01392
AFIX  43
H6    2    1.483084   -0.123953    0.640544    11.00000   -1.20000
AFIX   0
MOLE    1
I1    5    0.957186    0.221152    0.618069    11.00000    0.03792    0.05417 =
         0.04425    0.00265   -0.00133    0.00539
CL1   4    1.334693   -1.417047    0.352070    11.00000    0.03996    0.05647 =
         0.06247   -0.00312   -0.00210    0.00238
HKLF    4




REM  SIR92 run in space group P 2/c
REM wR2 = 0.1498, GooF = S = 1.116, Restrained GooF = 1.118 for all data
REM R1 = 0.0506 for 1244 Fo > 4sig(Fo) and 0.0564 for all 1423 data
REM 73 parameters refined using 6 restraints

END

WGHT      0.0895      0.4359

REM Highest difference peak  1.530,  deepest hole -1.333,  1-sigma level  0.219
Q1    1   0.9360 -0.0230  0.6191  11.00000  0.05    1.53
Q2    1   0.9660  0.4783  0.6142  11.00000  0.05    1.51
Q3    1   0.9809  0.2372  0.6946  11.00000  0.05    0.75
Q4    1   0.8578  0.2291  0.6446  11.00000  0.05    0.71
Q5    1   0.9470  0.2182  0.5441  11.00000  0.05    0.71
Q6    1   1.2267 -1.3989  0.3845  11.00000  0.05    0.65
Q7    1   1.3715 -1.4147  0.3393  11.00000  0.05    0.59
Q8    1   1.1234 -0.2246  0.6404  11.00000  0.05    0.56
Q9    1   1.0093 -0.1568  0.5274  11.00000  0.05    0.55
Q10   1   1.3431 -1.2446  0.3360  11.00000  0.05    0.54
Q11   1   1.3043 -1.6413  0.3672  11.00000  0.05    0.54
Q12   1   1.0561  0.2168  0.5909  11.00000  0.05    0.53
Q13   1   1.0403  0.4937  0.4918  11.00000  0.05    0.51
Q14   1   1.0411 -0.2651  0.8348  11.00000  0.05    0.48
Q15   1   1.2370  0.1159  0.5905  11.00000  0.05    0.47
Q16   1   1.3820 -0.3775  0.8030  11.00000  0.05    0.46
Q17   1   1.3284 -1.0623  0.3532  11.00000  0.05    0.46
Q18   1   1.3271 -0.0606  0.6734  11.00000  0.05    0.46
Q19   1   1.2280 -1.0509  0.3819  11.00000  0.05    0.43
Q20   1   1.2458  0.3103  0.5826  11.00000  0.05    0.43
;
_shelx_res_checksum              94122
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4-IPyHBr
_database_code_depnum_ccdc_archive 'CCDC 1995446'
loop_
_audit_author_name
_audit_author_address
'Vladimir Stilinovic'
;Department of Chemistry, Faculty of Science, University of Zagreb
Croatia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H5 I N, Br'
_chemical_formula_sum            'C5 H5 Br I N'
_chemical_formula_weight         285.91

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_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, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   4.3789(3)
_cell_length_b                   8.5332(7)
_cell_length_c                   9.9405(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.160(6)
_cell_angle_gamma                90
_cell_volume                     369.93(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1476
_cell_measurement_theta_min      4.0975
_cell_measurement_theta_max      35.4432

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.567
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    9.629
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.15441
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            1659
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.117
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             855
_reflns_number_gt                754
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_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_solution    
;
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112-122.
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1094P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.101(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         855
_refine_ls_number_parameters     30
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1573
_refine_ls_wR_factor_gt          0.1550
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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) . ?

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) . . ?

_refine_diff_density_max         1.574
_refine_diff_density_min         -2.093
_refine_diff_density_rms         0.291

_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
