#------------------------------------------------------------------------------
#$Date: 2021-03-26 04:09:39 +0200 (Fri, 26 Mar 2021) $
#$Revision: 263337 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/12/1561278.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_1561278
loop_
_publ_author_name
'Heinz, Benjamin'
'Djukanovic, Dimitrije'
'Filipponi, Paolo'
'Martin, Benjamin'
'Karaghiosoff, Konstantin'
'Knochel, Paul'
_publ_section_title
;
 Regioselective Difunctionalization of Pyridines via 3,4-Pyridynes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01208H
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H16 I N O S'
_chemical_formula_sum            'C15 H16 I N O S'
_chemical_formula_weight         385.25
_chemical_name_systematic
;
3-iodo-2-(isopropylthio)-4-(4-methoxyphenyl)pyridine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2021-01-20 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.114(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5870(3)
_cell_length_b                   6.1553(2)
_cell_length_c                   14.6215(5)
_cell_measurement_reflns_used    7033
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.9150
_cell_measurement_theta_min      2.4500
_cell_volume                     763.07(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14968
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_min         2.402
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_description       rod
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 1923 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.044(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4640
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0206
_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)+(0.0215P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0430
_refine_ls_wR_factor_ref         0.0439
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4430
_reflns_number_total             4640
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc01208h2.cif
_cod_data_source_block           test1_CCDC1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1561278
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.664
_shelx_estimated_absorpt_t_max   0.936
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.58737(2) 0.85001(3) 0.62175(2) 0.02248(5) Uani 1 1 d . . . . .
S1 S 0.82154(9) 0.57177(12) 0.78440(5) 0.02102(14) Uani 1 1 d . . . . .
C7 C 0.8309(4) 0.1859(5) 0.8811(3) 0.0300(7) Uani 1 1 d . . . . .
H7A H 0.848(3) 0.112(2) 0.8267(17) 0.045 Uiso 1 1 calc R U . . .
H7B H 0.721(3) 0.2016(6) 0.8807(18) 0.045 Uiso 1 1 calc R U . . .
H7C H 0.876(2) 0.105(3) 0.9338(15) 0.045 Uiso 1 1 calc R U . . .
C9 C 0.3023(3) 1.0472(4) 0.7287(2) 0.0180(5) Uani 1 1 d . . . . .
C13 C 0.0358(3) 1.1200(5) 0.6515(2) 0.0202(6) Uani 1 1 d . . . . .
H13 H -0.062(4) 1.0771(19) 0.6356(7) 0.024 Uiso 1 1 calc R U . . .
C3 C 0.4151(3) 0.9034(4) 0.7880(2) 0.0176(6) Uani 1 1 d . . . . .
C2 C 0.3920(3) 0.8600(11) 0.87897(17) 0.0214(5) Uani 1 1 d . . . . .
H2 H 0.303(3) 0.921(2) 0.9025(9) 0.026 Uiso 1 1 calc R U . . .
C12 C 0.0834(3) 1.3254(9) 0.62359(18) 0.0209(8) Uani 1 1 d . . . . .
N1 N 0.6257(3) 0.6391(4) 0.90709(18) 0.0220(5) Uani 1 1 d . . . . .
O1 O -0.0129(2) 1.4680(3) 0.57153(16) 0.0245(5) Uani 1 1 d . . . . .
C14 C 0.1452(3) 0.9855(5) 0.7044(2) 0.0194(5) Uani 1 1 d . . . . .
H14 H 0.1141(16) 0.857(6) 0.7232(9) 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5471(3) 0.8095(4) 0.75918(19) 0.0175(6) Uani 1 1 d . . . . .
C10 C 0.3488(3) 1.2513(5) 0.7005(2) 0.0212(6) Uani 1 1 d . . . . .
H10 H 0.465(4) 1.3004(16) 0.7185(6) 0.025 Uiso 1 1 calc R U . . .
C6 C 0.9074(3) 0.4089(5) 0.8845(2) 0.0188(6) Uani 1 1 d . . . . .
H6 H 0.8885(8) 0.485(3) 0.942(2) 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6503(3) 0.6792(4) 0.8207(2) 0.0175(5) Uani 1 1 d . . . . .
C1 C 0.4979(4) 0.7284(5) 0.9346(2) 0.0241(6) Uani 1 1 d . . . . .
H1 H 0.4792(9) 0.6993(14) 0.996(3) 0.029 Uiso 1 1 calc R U . . .
C15 C -0.1697(3) 1.3948(5) 0.5361(2) 0.0239(7) Uani 1 1 d . . . . .
H15A H -0.1642(3) 1.262(3) 0.5013(19) 0.036 Uiso 1 1 calc R U . . .
H15B H -0.2241(17) 1.505(3) 0.4960(16) 0.036 Uiso 1 1 calc R U . . .
H15C H -0.2264(15) 1.368(4) 0.5870(11) 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2412(4) 1.3875(5) 0.6489(2) 0.0233(7) Uani 1 1 d . . . . .
H11 H 0.2753(14) 1.528(5) 0.6299(8) 0.028 Uiso 1 1 calc R U . . .
C8 C 1.0848(4) 0.3970(5) 0.8841(2) 0.0279(8) Uani 1 1 d . . . . .
H8A H 1.1313(12) 0.317(4) 0.9337(15) 0.042 Uiso 1 1 calc R U . . .
H8B H 1.1262(11) 0.534(3) 0.8879(18) 0.042 Uiso 1 1 calc R U . . .
H8C H 1.1034(6) 0.333(4) 0.8304(14) 0.042 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C6 102.32(13) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C9 C10 118.7(3) . . ?
C14 C9 C3 120.1(3) . . ?
C10 C9 C3 121.1(3) . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C4 C3 C2 116.9(3) . . ?
C4 C3 C9 123.8(3) . . ?
C2 C3 C9 119.3(3) . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
O1 C12 C11 116.8(4) . . ?
O1 C12 C13 124.5(3) . . ?
C11 C12 C13 118.8(3) . . ?
C5 N1 C1 117.8(3) . . ?
C12 O1 C15 116.9(3) . . ?
C13 C14 C9 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 I1 120.2(2) . . ?
C5 C4 I1 119.64(19) . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C7 C6 C8 112.5(3) . . ?
C7 C6 S1 110.6(2) . . ?
C8 C6 S1 107.4(2) . . ?
C7 C6 H6 108.7 . . ?
C8 C6 H6 108.7 . . ?
S1 C6 H6 108.7 . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 S1 118.6(2) . . ?
C4 C5 S1 119.3(2) . . ?
N1 C1 C2 123.8(3) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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 2.107(3) . ?
S1 C5 1.769(3) . ?
S1 C6 1.830(3) . ?
C7 C6 1.520(4) . ?
C7 H7A 0.95(2) . ?
C7 H7B 0.95(2) . ?
C7 H7C 0.95(2) . ?
C9 C14 1.393(4) . ?
C9 C10 1.400(4) . ?
C9 C3 1.486(4) . ?
C13 C14 1.391(4) . ?
C13 C12 1.409(6) . ?
C13 H13 0.88(4) . ?
C3 C4 1.395(4) . ?
C3 C2 1.401(4) . ?
C2 C1 1.382(5) . ?
C2 H2 0.96(4) . ?
C12 O1 1.354(5) . ?
C12 C11 1.401(4) . ?
N1 C5 1.336(4) . ?
N1 C1 1.344(4) . ?
O1 C15 1.437(3) . ?
C14 H14 0.89(4) . ?
C4 C5 1.409(4) . ?
C10 C11 1.380(4) . ?
C10 H10 1.03(3) . ?
C6 C8 1.526(4) . ?
C6 H6 1.00(4) . ?
C1 H1 0.95(4) . ?
C15 H15A 0.967(19) . ?
C15 H15B 0.967(19) . ?
C15 H15C 0.967(19) . ?
C11 H11 0.97(4) . ?
C8 H8A 0.92(2) . ?
C8 H8B 0.92(2) . ?
C8 H8C 0.92(2) . ?
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
C14 C9 C3 C4 117.4(3) . . . . ?
C10 C9 C3 C4 -66.2(4) . . . . ?
C14 C9 C3 C2 -63.8(4) . . . . ?
C10 C9 C3 C2 112.7(4) . . . . ?
C4 C3 C2 C1 -0.3(6) . . . . ?
C9 C3 C2 C1 -179.2(4) . . . . ?
C14 C13 C12 O1 179.5(3) . . . . ?
C14 C13 C12 C11 1.0(5) . . . . ?
C11 C12 O1 C15 172.7(3) . . . . ?
C13 C12 O1 C15 -5.8(4) . . . . ?
C12 C13 C14 C9 -1.6(5) . . . . ?
C10 C9 C14 C13 1.4(4) . . . . ?
C3 C9 C14 C13 177.9(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C9 C3 C4 C5 178.4(2) . . . . ?
C2 C3 C4 I1 176.8(3) . . . . ?
C9 C3 C4 I1 -4.3(3) . . . . ?
C14 C9 C10 C11 -0.6(5) . . . . ?
C3 C9 C10 C11 -177.1(3) . . . . ?
C5 S1 C6 C7 83.5(2) . . . . ?
C5 S1 C6 C8 -153.3(2) . . . . ?
C1 N1 C5 C4 -0.3(4) . . . . ?
C1 N1 C5 S1 177.7(2) . . . . ?
C3 C4 C5 N1 0.8(4) . . . . ?
I1 C4 C5 N1 -176.5(2) . . . . ?
C3 C4 C5 S1 -177.2(2) . . . . ?
I1 C4 C5 S1 5.5(3) . . . . ?
C6 S1 C5 N1 4.6(3) . . . . ?
C6 S1 C5 C4 -177.4(2) . . . . ?
C5 N1 C1 C2 -0.5(5) . . . . ?
C3 C2 C1 N1 0.8(7) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
O1 C12 C11 C10 -178.8(3) . . . . ?
C13 C12 C11 C10 -0.3(5) . . . . ?
