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_4513879
_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         'C33 H23 F3 N2 O4'
_chemical_formula_sum            'C33 H23 F3 N2 O4'
_chemical_formula_weight         568.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-09-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.889(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.6794(8)
_cell_length_b                   5.8892(2)
_cell_length_c                   20.8559(7)
_cell_measurement_reflns_used    3622
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.25
_cell_measurement_theta_min      4.29
_cell_volume                     2630.78(16)
_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)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  0.0540
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17269
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        66.745
_diffrn_reflns_theta_max         66.745
_diffrn_reflns_theta_min         4.291
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.0834 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.8787.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0471P)^2^+0.8059P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3397
_reflns_number_total             4529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b00728_si_002.cif
_cod_data_source_block           p21c
_cod_depositor_comments
'Adding full bibliography for 4513878--4513880.cif.'
_cod_database_code               4513879
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.806
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C11(H11), C12(H12), C13(H13), C16(H16), C20(H20), C21(H21),
 C22(H22), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33)
;
_shelx_res_checksum              10079
_shelx_hkl_checksum              70918
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'