Alkyl lithium-catalyzed benzylic C-H bond addition of alkyl pyridines to α-alkenes.
Luo, Yan-Long; Liu, Yu-Feng; Guan, Bing-Tao; Organic & biomolecular chemistry 18 (2020) 6622–6626; doi:10.1039/d0ob01499k

data_7157671
_publ_section_title
;
 Alkyl lithium-catalyzed benzylic C-H bond addition of alkyl pyridines to
 \a-alkenes.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6622
_journal_page_last               6626
_journal_paper_doi               10.1039/d0ob01499k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C7 H3 N2 O6, C7 H4 N2 O6, C12 H18 N'
_chemical_formula_sum            'C26 H25 N5 O12'
_chemical_formula_weight         599.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-11 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                108.0000(10)
_cell_angle_beta                 99.4130(10)
_cell_angle_gamma                106.6790(10)
_cell_formula_units_Z            2
_cell_length_a                   10.03310(10)
_cell_length_b                   11.89880(10)
_cell_length_c                   13.4124(2)
_cell_measurement_reflns_used    19514
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      79.0890
_cell_measurement_theta_min      4.1980
_cell_volume                     1401.73(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -24.00  94.00   0.50    0.50    --    5.00  57.00-120.00  236
  2  \w    -84.00  39.00   0.50    0.50    --  -50.10  72.00  30.00  246
  3  \w    -82.00  39.00   0.50    0.50    --  -50.10  38.00-120.00  242
  4  \w   -140.00 -21.00   0.50    0.50    --  -50.10 -52.00  51.64  238
  5  \w   -140.00 -17.00   0.50    0.50    --  -50.10 -72.00 120.00  246
  6  \w   -140.00 -17.00   0.50    0.50    --  -50.10 -33.00 -50.17  246
  7  \w   -199.00 -81.00   0.50    0.50    -- -110.00 -57.00 -90.00  236
  8  \w   -143.00 -21.00   0.50    0.50    -- -110.00  72.00  60.00  244
  9  \w   -161.00 -21.00   0.50    0.50    -- -110.00  19.00  60.00  280
 10  \w   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 -60.00  244
 11  \w   -143.00 -21.00   0.50    0.50    -- -110.00  72.00  90.00  244
 12  \w   -199.00 -80.00   0.50    0.50    -- -110.00 -64.00  64.12  238
 13  \w   -139.00 -21.00   0.50    0.50    -- -110.00  57.00 120.00  236
 14  \w   -143.00 -21.00   0.50    0.50    -- -110.00  72.00-150.00  244
 15  \w   -143.00 -21.00   0.50    0.50    -- -110.00  72.00-180.00  244
 16  \w   -199.00 -59.00   0.50    0.50    -- -110.00 -19.00 -30.00  280
 17  \w   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 -90.00  244
 18  \w   -143.00 -21.00   0.50    0.50    -- -110.00  72.00   0.00  244
 19  \w   -139.00 -21.00   0.50    0.50    -- -110.00  57.00-180.00  236
 20  \w   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 -30.00  244
 21  \w   -199.00 -81.00   0.50    0.50    -- -110.00 -46.00-113.60  236
 22  \w   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 120.00  244
 23  \w   -199.00 -79.00   0.50    0.50    -- -110.00 -67.00 152.66  240
 24  \w   -140.00 -20.00   0.50    0.50    --  -50.10 -63.00 147.48  240
 25  \w    -80.00  39.00   0.50    0.50    --  -50.10  57.00 -30.00  238
 26  \w   -140.00 -21.00   0.50    0.50    --  -50.10 -57.00-150.00  238
 27  \w   -140.00 -21.00   0.50    0.50    --  -50.10 -60.00 -74.49  238
 28  \w   -199.00 -79.00   0.50    0.50    -- -110.00 -38.00-180.00  240
 29  \w   -199.00-146.00   0.50    0.50    -- -110.00 -38.00 -60.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0428342000
_diffrn_orient_matrix_UB_12      0.0385680000
_diffrn_orient_matrix_UB_13      -0.0931590000
_diffrn_orient_matrix_UB_21      0.0740172000
_diffrn_orient_matrix_UB_22      0.1389523000
_diffrn_orient_matrix_UB_23      0.0798995000
_diffrn_orient_matrix_UB_31      0.1432261000
_diffrn_orient_matrix_UB_32      -0.0222050000
_diffrn_orient_matrix_UB_33      0.0271012000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34190
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.542
_diffrn_reflns_theta_min         3.606
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.980
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0052(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0572
_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^)+(0.0970P)^2^+0.2560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1780
_refine_ls_wR_factor_ref         0.1816
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5241
_reflns_number_total             5893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01499k2.cif
_cod_data_source_block           p20190605b
_cod_depositor_comments          'Adding full bibliography for 7157671.cif.'
_cod_database_code               7157671
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H21N3O6
_shelx_estimated_absorpt_t_max   0.843
_shelx_estimated_absorpt_t_min   0.771
_reflns_odcompleteness_completeness 97.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C17(H17), C19(H19), C22(H22),
 C24(H24), C26(H26)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O7(H7A)
;
_shelx_res_checksum              35865
_shelx_hkl_checksum              17498
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.109
_oxdiff_exptl_absorpt_empirical_full_min 0.648