Merging C–H Bond Functionalization with Amide Alcoholysis: En Route to 2-Aminopyridines
Kumar, Dinesh; Vemula, Sandeep R.; Cook, Gregory R.; ACS Catalysis 6 (2016) 3531–; doi:10.1021/acscatal.6b00728

data_4513880
_publ_section_title
;
 Merging C--H Bond Functionalization with Amide Alcoholysis: En Route to
 2-Aminopyridines
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3531
_journal_paper_doi               10.1021/acscatal.6b00728
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C26 H20 N2 O'
_chemical_formula_sum            'C26 H20 N2 O'
_chemical_formula_weight         376.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                66.910(2)
_cell_angle_beta                 68.341(3)
_cell_angle_gamma                69.341(2)
_cell_formula_units_Z            4
_cell_length_a                   12.5358(5)
_cell_length_b                   12.9306(5)
_cell_length_c                   14.2350(6)
_cell_measurement_reflns_used    6092
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.691
_cell_measurement_theta_min      5.916
_cell_volume                     1913.41(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15820
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        66.724
_diffrn_reflns_theta_max         66.723
_diffrn_reflns_theta_min         5.916
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1233 before and 0.0654 after correction. The Ratio of minimum to maximum transmission is 0.7949. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         6483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0675
_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^)+(0.0942P)^2^+1.6022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.2035
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4626
_reflns_number_total             6483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b00728_si_004.cif
_cod_data_source_block           cu_syr1_0m
_cod_depositor_comments
'Adding full bibliography for 4513878--4513880.cif.'
_cod_database_code               4513880
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.884
_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
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C17(H17),
 C18(H18), C19(H19), C1A(H1A), C1C(H1C), C1D(H1D), C1E(H1E), C1F(H1F), C1G(H1G),
  C1K(H1K), C1L(H1L), C1O(H1O), C1R(H1R), C1S(H1S), C1T(H1T), C1V(H1V),
 C1X(H1X), C1Y(H1Y), C1Z(H1Z), C20(H20), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C1B(H1BA,H1BB,H1BC), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              94444
_shelx_hkl_checksum              55152
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'