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_4513878
_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         'C30 H20 N2 O'
_chemical_formula_sum            'C30 H20 N2 O'
_chemical_formula_weight         424.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.0933(2)
_cell_length_b                   20.0387(4)
_cell_length_c                   23.2417(5)
_cell_measurement_reflns_used    6157
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.370
_cell_measurement_theta_min      4.398
_cell_volume                     4235.05(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      296.15
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.972
_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  0.0390
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21609
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.702
_diffrn_reflns_theta_min         2.912
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0679 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.8867.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       plate
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2498 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         7119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0454P)^2^+0.2425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.900
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                6359
_reflns_number_total             7119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b00728_si_003.cif
_cod_data_source_block           cu_dxk1_0m
_cod_depositor_comments
'Adding full bibliography for 4513878--4513880.cif.'
_cod_database_code               4513878
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.852
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33),
 C36(H36), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44), C46(H46),
  C47(H47), C51(H51), C54(H54), C55(H55), C56(H56), C57(H57), C58(H58),
 C59(H59), C60(H60)
;
_shelx_res_checksum              49410
_shelx_hkl_checksum              21962
_olex2_submission_special_instructions 'No special instructions were received'