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_1561279
_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         'C17 H23 N O2 Si'
_chemical_formula_sum            'C17 H23 N O2 Si'
_chemical_formula_weight         301.45
_chemical_name_systematic
;
2-ethoxy-4-(4-methoxyphenyl)-3-(trimethylsilyl)pyridine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.9518(6)
_cell_length_b                   6.9485(2)
_cell_length_c                   15.9226(3)
_cell_measurement_reflns_used    14903
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.2940
_cell_measurement_theta_min      2.6130
_cell_volume                     3424.45(14)
_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 0.996
_diffrn_measured_fraction_theta_max 0.997
_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  0.0437
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            65322
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_min         2.558
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84311
_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    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.449
_exptl_crystal_size_mid          0.409
_exptl_crystal_size_min          0.292
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 3866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         10423
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0406
_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/[\s^2^(Fo^2^)+(0.0497P)^2^+0.5858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                8971
_reflns_number_total             10423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01208h2.cif
_cod_data_source_block           test1_CCDC2
_cod_database_code               1561279
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.960
_shelxl_version_number           2014-3
_shelx_res_checksum              77323
_shelx_hkl_checksum              94982