#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:35:48 +0300 (Fri, 05 May 2023) $
#$Revision: 283508 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/64/7246471.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246471
loop_
_publ_author_name
'Chanmungkalakul, Supphachok'
'Huang, Shiqing'
'Wu, Xia'
'Ang, Esther Cai Xia'
'Yang, Zi-Qi'
'Li, Yongxin'
'Yan, Xiaoyu'
'Tan, Choon-Hong'
'Tan, Davin'
'Liu, Xiaogang'
_publ_section_title
;
 Ground-state intramolecular proton transfer inhibits the selective
 methylation on quinoline and pyridine derivatives.
;
_journal_issue                   15
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              10599
_journal_page_last               10603
_journal_paper_doi               10.1039/d3cp00123g
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C5 H5 I N2'
_chemical_formula_weight         220.01
_space_group_crystal_system      tetragonal
_space_group_IT_number           139
_space_group_name_Hall           '-I 4 2'
_space_group_name_H-M_alt        'I 4/m m m'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2021-12-13 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.3872(3)
_cell_length_b                   10.3872(3)
_cell_length_c                   13.2209(6)
_cell_measurement_reflns_used    9194
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      44.0853
_cell_measurement_theta_min      2.4936
_cell_volume                     1426.45(9)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24275
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         53.91
_diffrn_reflns_theta_min         2.49
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    4.391
_exptl_absorpt_correction_T_max  0.45
_exptl_absorpt_correction_T_min  0.17
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.049
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_refine_diff_density_max         1.298
_refine_diff_density_min         -1.762
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         2491
_refine_ls_number_restraints     88
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0391P)²+3.0864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1838
_reflns_number_total             2491
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cp00123g2.cif
_cod_data_source_block           tch206m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7246469--7246475.cif.
;
_cod_original_cell_volume        1426.45(10)
_cod_database_code               7246471
_shelx_res_file
;

TITL tch206m in I4/mmm
    tch206m.res
    created by SHELXL-2018/3 at 15:14:44 on 22-Sep-2021
CELL  0.71073  10.3872  10.3872  13.2209   90.000   90.000   90.000
ZERR    8.000   0.0003   0.0003   0.0006    0.000    0.000    0.000
LATT 2
SYMM -X, -Y, Z
SYMM -Y, X, Z
SYMM Y, -X, Z
SYMM -X, Y, -Z
SYMM X, -Y, -Z
SYMM Y, X, -Z
SYMM -Y, -X, -Z
SFAC C  H  I  N
UNIT 40  40  8  16
L.S. 18
BOND
acta
sadi 0.01 c1 c3 c1 c4
FMAP 2
eadp c2 c5
eadp c3 c4
rigu 0.01 C1 > C5
simu 0.002 C1 > C5
PLAN 5
SIZE 0.22 0.28 0.32
TEMP -173.0
WGHT    0.039100    3.086400
FVAR       0.12579
part -1 10.25
C1    1    0.525773    0.209761    0.502100    10.25000    0.01337    0.02469 =
         0.02250    0.00492    0.00003    0.00024
AFIX 137
H1A   2    0.495414    0.188867    0.570336    10.25000   -1.50000
H1B   2    0.494988    0.144378    0.454448    10.25000   -1.50000
H1C   2    0.492588    0.294343    0.482132    10.25000   -1.50000
AFIX  66

N1    4    0.932502    0.217147    0.498336    10.25000    0.01519    0.01799 =
         0.02351    0.00817    0.00204   -0.00093
C2    1    0.867018    0.224757    0.589829    10.25000    0.01638    0.01309 =
         0.02168    0.00954    0.00221   -0.00262
AFIX  43
H2    2    0.913699    0.231628    0.651384    10.25000   -1.20000
AFIX  65
C3    1    0.733235    0.222313    0.591257    10.25000    0.01569    0.01027 =
         0.01703    0.00836    0.00093   -0.00203
AFIX  43
H3    2    0.688481    0.227515    0.653789    10.25000   -1.20000
AFIX  65
N2    4    0.664934    0.212260    0.501193    10.25000    0.01367    0.01352 =
         0.01739    0.00725   -0.00006   -0.00110
C4    1    0.730416    0.204649    0.409699    10.25000    0.01569    0.01027 =
         0.01703    0.00836    0.00093   -0.00203
AFIX  43
H4    2    0.683734    0.197778    0.348144    10.25000   -1.20000
AFIX  65
C5    1    0.864199    0.207093    0.408269    10.25000    0.01638    0.01309 =
         0.02168    0.00954    0.00221   -0.00262
AFIX  43
H5    2    0.908952    0.201891    0.345737    10.25000   -1.20000
AFIX   0
part 0
I1    3    0.500000    0.000000    0.250000    10.12500    0.01832    0.01832 =
         0.01633    0.00000    0.00000    0.00000
I2    3    0.500000    0.500000    0.690698    10.12500    0.02210    0.02210 =
         0.01597    0.00000    0.00000    0.00000

HKLF 4




REM  tch206m in I4/mmm
REM wR2 = 0.094224, GooF = S = 1.02103, Restrained GooF = 1.01381 for all data
REM R1 = 0.035881 for 1838 Fo > 4sig(Fo) and 0.056540 for all 2491 data
REM 46 parameters refined using 88 restraints

END

WGHT      0.0394      3.0634

REM Highest difference peak  1.298,  deepest hole -1.762,  1-sigma level  0.174
Q1    1   0.5000  0.5000  0.5542  10.12500  0.05    1.28
Q2    1   0.9227  0.2471  0.5000  10.50000  0.05    0.87
Q3    1   0.4704  0.0000  0.2102  10.50000  0.05    0.77
Q4    1   0.5000  0.5000  0.5952  10.12500  0.05    0.70
Q5    1   0.7967  0.2033  0.4290  10.50000  0.05    0.68
;
_shelx_res_checksum              11411
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'-x, y, -z'
'x, -y, -z'
'y, x, -z'
'-y, -x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y+1/2, x+1/2, -z+1/2'
'-y+1/2, -x+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z'
'-y, x, -z'
'x, -y, z'
'-x, y, z'
'-y, -x, z'
'y, x, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5258(3) 0.2098(4) 0.5021(11) 0.0202(7) Uani d U P D 0.25 A -1
H H1A 0.495414 0.188867 0.570336 0.030000 Uiso calc U P R 0.25 A -1
H H1B 0.494988 0.144378 0.454448 0.030000 Uiso calc U P R 0.25 A -1
H H1C 0.492588 0.294343 0.482132 0.030000 Uiso calc U P R 0.25 A -1
N N1 0.93250(14) 0.2171(3) 0.4983(6) 0.0189(5) Uani d U P G 0.25 A -1
C C2 0.8670(5) 0.2248(5) 0.5898(4) 0.0171(5) Uani d U P G 0.25 A -1
H H2 0.913699 0.231628 0.651384 0.020000 Uiso calc U P R 0.25 A -1
C C3 0.7332(5) 0.2223(5) 0.5913(4) 0.0143(5) Uani d U P DG 0.25 A -1
H H3 0.688481 0.227515 0.653789 0.017000 Uiso calc U P R 0.25 A -1
N N2 0.66493(14) 0.2123(2) 0.5012(5) 0.0149(4) Uani d U P G 0.25 A -1
C C4 0.7304(5) 0.2046(5) 0.4097(4) 0.0143(5) Uani d U P DG 0.25 A -1
H H4 0.683734 0.197778 0.348144 0.017000 Uiso calc U P R 0.25 A -1
C C5 0.8642(5) 0.2071(5) 0.4083(4) 0.0171(5) Uani d U P G 0.25 A -1
H H5 0.908952 0.201891 0.345737 0.020000 Uiso calc U P R 0.25 A -1
I I1 0.500000 0.000000 0.250000 0.01766(5) Uani d T P S 1 . .
I I2 0.500000 0.500000 0.69070(2) 0.02006(5) Uani d T P S 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0134(11) 0.0247(14) 0.0225(15) 0.0002(9) 0.000(3) 0.005(4)
N1 0.0152(9) 0.0180(10) 0.0235(10) -0.0009(8) 0.0020(18) 0.0082(16)
C2 0.0164(7) 0.0131(12) 0.0217(8) -0.0026(8) 0.0022(13) 0.0095(10)
C3 0.0157(7) 0.0103(12) 0.0170(7) -0.0020(8) 0.0009(12) 0.0084(9)
N2 0.0137(8) 0.0135(8) 0.0174(8) -0.0011(7) -0.0001(17) 0.0072(15)
C4 0.0157(7) 0.0103(12) 0.0170(7) -0.0020(8) 0.0009(12) 0.0084(9)
C5 0.0164(7) 0.0131(12) 0.0217(8) -0.0026(8) 0.0022(13) 0.0095(10)
I1 0.01832(6) 0.01832(6) 0.01633(9) 0.000000 0.000000 0.000000
I2 0.02210(7) 0.02210(7) 0.01597(9) 0.000000 0.000000 0.000000
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C5 . . 120.000000 ?
C3 C2 N1 . . 120.000000 ?
C2 C3 N2 . . 120.000000 ?
C3 N2 C4 . . 120.000000 ?
C3 N2 C1 . . 120.3(4) ?
C4 N2 C1 . . 119.7(4) ?
C5 C4 N2 . . 120.000000 ?
C4 C5 N1 . . 120.000000 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.446(4) ?
N1 C2 . 1.390000 ?
N1 C5 . 1.390000 ?
C2 C3 . 1.390000 ?
C3 N2 . 1.390000 ?
N2 C4 . 1.390000 ?
C4 C5 . 1.390000 ?
