Regioselective Difunctionalization of Pyridines via 3,4-Pyridynes
Heinz, Benjamin; Djukanovic, Dimitrije; Filipponi, Paolo; Martin, Benjamin; Karaghiosoff, Konstantin; Knochel, Paul; Chemical Science  (2021) –; doi:10.1039/D1SC01208H

data_1561278
_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
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
;
_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       '\w 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/[\s^2^(Fo^2^)+(0.0215P)^2^] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_estimated_absorpt_t_min   0.664
_shelx_estimated_absorpt_t_max   0.936
_shelxl_version_number           2014-3
_shelx_res_checksum              17499
_shelx_hkl_checksum              47333