Base-Mediated Regiospecific Cascade Synthesis of N-(2-Pyridyl)pyrroles from N-Propargylic β-Enaminones
Shen, Jinhai; Yang, Xifa; Wang, Fuyuan; Wang, Yue; Cheng, Guolin; Cui, Xiuling; RSC Adv.  (2016) –; doi:10.1039/C6RA08987A

data_7225233
_publ_section_title
;
 Base-Mediated Regiospecific Cascade Synthesis of N-(2-Pyridyl)pyrroles
 from N-Propargylic \b-Enaminones
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA08987A
_journal_year                    2016
_chemical_formula_moiety         'C36 H28 N2 O'
_chemical_formula_sum            'C36 H28 N2 O'
_chemical_formula_weight         504.60
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-07-09
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2014-04-01 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                104.808(8)
_cell_angle_beta                 91.834(7)
_cell_angle_gamma                113.724(9)
_cell_formula_units_Z            2
_cell_length_a                   9.4141(9)
_cell_length_b                   11.6808(12)
_cell_length_c                   14.2260(11)
_cell_measurement_reflns_used    3012
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.4883
_cell_measurement_theta_min      3.2493
_cell_volume                     1368.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   -1.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -60.0000 26

  2 omega  -47.00   23.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   45.0000  -60.0000 70

  3 omega -105.00  -34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -60.0000 71

  4 omega  -90.00  -34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000   90.0000 56

  5 omega -100.00  -13.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -180.0000 87

  6 omega  -17.00   26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000 -120.0000 43

  7 omega  -90.00   15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  111.0000  -60.0000 105

  8 omega  -45.00   25.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  150.0000 70

  9 omega   11.00   38.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -19.0000    0.0000 27

 10 omega   45.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 53

 11 omega   51.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 43

 12 omega   90.00  174.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   30.0000 84

 13 omega   52.00   92.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 40

 14 omega   47.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 58

 15 omega   48.00   74.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  120.0000 26

 16 omega   43.00   96.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 53

 17 omega   58.00  146.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -90.0000 88

 18 omega   49.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 39

 19 omega   43.00   87.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 44

 20 omega   47.00   86.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 39

 21 omega   39.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 46

 22 omega   44.00  100.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 56

 23 omega   41.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 64

 24 omega   39.00   65.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 26

 25 omega   66.00  171.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  150.0000 105

 26 omega   90.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 26

 27 omega  -72.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000 -120.0000 98

 28 omega -111.00  -21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -61.0000   60.0000 90

 29 omega -111.00  -21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -61.0000 -120.0000 90

 30 omega   26.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  -30.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0508663000
_diffrn_orient_matrix_UB_12      0.1475630000
_diffrn_orient_matrix_UB_13      0.0169375000
_diffrn_orient_matrix_UB_21      -0.1731482000
_diffrn_orient_matrix_UB_22      -0.0247149000
_diffrn_orient_matrix_UB_23      -0.0205066000
_diffrn_orient_matrix_UB_31      -0.0116689000
_diffrn_orient_matrix_UB_32      0.0182418000
_diffrn_orient_matrix_UB_33      0.1101956000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9859
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.25
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+0.0614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1545
_reflns_number_gt                3649
_reflns_number_total             4861
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra08987a2.cif
_cod_data_source_block           201307114
_cod_original_cell_volume        1368.4(2)
_cod_database_code               7225233
_chemical_oxdiff_formula         C20H20N4O4
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C22(H22), C26(H26), C27(H27), C28(H28), C29(H29),
  C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C24(H24A,H24B,H24C)
;