#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:35:48 +0300 (Fri, 05 May 2023) $
#$Revision: 283508 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/64/7246475.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_7246475
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            'C6 H8 I N S'
_chemical_formula_weight         253.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 91.042(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9824(9)
_cell_length_b                   15.4554(19)
_cell_length_c                   7.8105(11)
_cell_measurement_reflns_used    6628
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      35.3796
_cell_measurement_theta_min      2.9178
_cell_volume                     842.74(19)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CMOS 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  0.0724
_diffrn_reflns_av_unetI/netI     0.0920
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26220
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         43.06
_diffrn_reflns_theta_min         2.64
_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    3.966
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_correction_T_min  0.55
_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            colourless
_exptl_crystal_density_diffrn    1.995
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.070
_refine_diff_density_min         -1.898
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         6236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0191P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0693
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3762
_reflns_number_total             6236
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cp00123g2.cif
_cod_data_source_block           tch216m
_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_database_code               7246475
_shelx_res_file
;

TITL tch216m in P2(1)/c
    tch216m.res
    created by SHELXL-2018/3 at 09:35:02 on 11-Nov-2021
CELL 0.71073   6.98240  15.45540   7.81050  90.0000  91.0422  90.0000
ZERR    4.00   0.00090   0.00190   0.00110   0.0000   0.0065   0.0000
LATT 1
SYMM -X, 1/2+Y, 1/2-Z
SFAC C  H  I  N  S
UNIT 24  32  4  4  4
L.S. 10
BOND
acta
FMAP 2
PLAN 10
SIZE 0.10 0.12 0.14
TEMP -173.0
WGHT    0.019100
FVAR       0.14745
C1    1    0.288365    0.070020    0.701121    11.00000    0.02217    0.01925 =
         0.02202    0.00259    0.00463   -0.00535
AFIX 137
H1A   2    0.284009    0.048959    0.582765    11.00000   -1.50000
H1B   2    0.175905    0.048905    0.761688    11.00000   -1.50000
H1C   2    0.405017    0.048788    0.758754    11.00000   -1.50000
AFIX   0
C2    1    0.507509    0.210722    0.609843    11.00000    0.01207    0.01521 =
         0.00956    0.00103    0.00021   -0.00036
C3    1    0.643362    0.151873    0.554513    11.00000    0.01664    0.01533 =
         0.01737   -0.00061    0.00242    0.00197
AFIX  43
H3    2    0.619851    0.091471    0.562320    11.00000   -1.20000
AFIX   0
C4    1    0.813583    0.181945    0.487785    11.00000    0.01291    0.02806 =
         0.01897   -0.00143    0.00299    0.00579
AFIX  43
H4    2    0.906111    0.141841    0.448586    11.00000   -1.20000
AFIX   0
C5    1    0.850171    0.270172    0.477683    11.00000    0.01653    0.02840 =
         0.01612    0.00297    0.00368   -0.00356
AFIX  43
H5    2    0.967670    0.290896    0.433961    11.00000   -1.20000
AFIX   0
C6    1    0.712251    0.326724    0.532479    11.00000    0.01802    0.02050 =
         0.02072    0.00421   -0.00024   -0.00395
AFIX  43
H6    2    0.733091    0.387370    0.526051    11.00000   -1.20000
AFIX   0
I1    3    0.206276    0.442857    0.698275    11.00000    0.01468    0.01365 =
         0.01807   -0.00064    0.00256    0.00112
N1    4    0.547934    0.295894    0.595134    11.00000    0.01410    0.01495 =
         0.01706    0.00067    0.00078    0.00241
AFIX  43
H1    2    0.461433    0.333372    0.628606    11.00000   -1.20000
AFIX   0
S1    5    0.288667    0.186560    0.701405    11.00000    0.01322    0.01994 =
         0.02061   -0.00124    0.00542   -0.00125
HKLF 4




REM  tch216m in P2(1)/c
REM wR2 = 0.069285, GooF = S = 0.97758, Restrained GooF = 0.97758 for all data
REM R1 = 0.041480 for 3762 Fo > 4sig(Fo) and 0.100019 for all 6236 data
REM 83 parameters refined using 0 restraints

END

WGHT      0.0184      0.0000

REM Highest difference peak  1.070,  deepest hole -1.898,  1-sigma level  0.254
Q1    1   0.4974  0.1532  0.4227  11.00000  0.05    1.07
Q2    1   0.5791  0.1812  0.5813  11.00000  0.05    1.02
Q3    1   0.4070  0.2451  0.8640  11.00000  0.05    1.01
Q4    1   1.0700  0.3281  0.6645  11.00000  0.05    1.00
Q5    1   1.1322  0.3220  0.4994  11.00000  0.05    0.94
Q6    1   0.5415 -0.0367  0.6466  11.00000  0.05    0.94
Q7    1   0.4114  0.1775  0.8819  11.00000  0.05    0.94
Q8    1   0.6151  0.0344  0.7163  11.00000  0.05    0.93
Q9    1   0.2800  0.1309  0.4580  11.00000  0.05    0.92
Q10   1   0.5113  0.0064  0.8802  11.00000  0.05    0.92
;
_shelx_res_checksum              74171
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'
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 0.2884(3) 0.07002(13) 0.7011(3) 0.0211(4) Uani d . . . 1 . .
H H1A 0.284009 0.048959 0.582765 0.032000 Uiso calc U . R 1 . .
H H1B 0.175905 0.048905 0.761688 0.032000 Uiso calc U . R 1 . .
H H1C 0.405017 0.048788 0.758754 0.032000 Uiso calc U . R 1 . .
C C2 0.5075(3) 0.21072(12) 0.6098(2) 0.0123(3) Uani d . . . 1 . .
C C3 0.6434(3) 0.15187(13) 0.5545(3) 0.0164(4) Uani d . . . 1 . .
H H3 0.619851 0.091471 0.562320 0.020000 Uiso calc U . R 1 . .
C C4 0.8136(3) 0.18194(14) 0.4878(3) 0.0199(4) Uani d . . . 1 . .
H H4 0.906111 0.141841 0.448586 0.024000 Uiso calc U . R 1 . .
C C5 0.8502(3) 0.27017(14) 0.4777(3) 0.0203(4) Uani d . . . 1 . .
H H5 0.967670 0.290896 0.433961 0.024000 Uiso calc U . R 1 . .
C C6 0.7123(3) 0.32672(14) 0.5325(3) 0.0198(4) Uani d . . . 1 . .
H H6 0.733091 0.387370 0.526051 0.024000 Uiso calc U . R 1 . .
I I1 0.20628(2) 0.44286(2) 0.69827(2) 0.01544(4) Uani d . . . 1 . .
N N1 0.5479(2) 0.29589(10) 0.5951(2) 0.0154(3) Uani d . . . 1 . .
H H1 0.461433 0.333372 0.628606 0.018000 Uiso calc U . R 1 . .
S S1 0.28867(7) 0.18656(3) 0.70141(7) 0.01786(10) Uani d . . . 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 0.0222(10) 0.0192(10) 0.0220(11) -0.0054(7) 0.0046(8) 0.0026(8)
C2 0.0121(8) 0.0152(8) 0.0096(8) -0.0004(6) 0.0002(6) 0.0010(6)
C3 0.0166(8) 0.0153(9) 0.0174(10) 0.0020(7) 0.0024(7) -0.0006(7)
C4 0.0129(8) 0.0281(11) 0.0190(10) 0.0058(7) 0.0030(7) -0.0014(8)
C5 0.0165(9) 0.0284(11) 0.0161(10) -0.0036(8) 0.0037(7) 0.0030(8)
C6 0.0180(9) 0.0205(9) 0.0207(10) -0.0039(7) -0.0002(8) 0.0042(8)
I1 0.01468(6) 0.01365(6) 0.01807(7) 0.00112(4) 0.00256(4) -0.00064(5)
N1 0.0141(7) 0.0149(7) 0.0171(8) 0.0024(6) 0.0008(6) 0.0007(6)
S1 0.0132(2) 0.0199(2) 0.0206(2) -0.00125(17) 0.00542(18) -0.00124(19)
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'
S S 0.1246 0.1234 '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
N1 C2 C3 . . 117.81(17) ?
N1 C2 S1 . . 115.49(14) ?
C3 C2 S1 . . 126.69(15) ?
C4 C3 C2 . . 119.50(18) ?
C3 C4 C5 . . 120.66(18) ?
C6 C5 C4 . . 118.40(19) ?
N1 C6 C5 . . 119.73(19) ?
C6 N1 C2 . . 123.90(17) ?
C2 S1 C1 . . 102.43(9) ?
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 S1 . 1.801(2) ?
C2 N1 . 1.352(2) ?
C2 C3 . 1.389(3) ?
C2 S1 . 1.7394(19) ?
C3 C4 . 1.387(3) ?
C4 C5 . 1.390(3) ?
C5 C6 . 1.375(3) ?
C6 N1 . 1.343(3) ?
