The Elusive Paal-Knorr Intermediates in the Trofimov Synthesis of Pyrroles: Experimental and Theoretical Studies.
Sączewski, Jarosław; Fedorowicz, Joanna; Gdaniec, Maria; Wiśniewska, Paulina; Sieniawska, Emilia; Drażba, Zuzanna; Rzewnicka, Justyna; Balewski, Łukasz; The Journal of organic chemistry 82 (2017) 9737–9743; doi:10.1021/acs.joc.7b01851

data_4033080
_publ_section_title
;
 The Elusive Paal-Knorr Intermediates in the Trofimov Synthesis of
 Pyrroles: Experimental and Theoretical Studies.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9737
_journal_page_last               9743
_journal_paper_doi               10.1021/acs.joc.7b01851
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C14 H10 N2 O3'
_chemical_formula_sum            'C14 H10 N2 O3'
_chemical_formula_weight         254.24
_chemical_name_systematic
(E)-1-(3-Oxobut-1-enyl)isoxazolo[3,4-b]quinolin-3(1H)-one
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.1572(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.83581(5)
_cell_length_b                   9.67555(10)
_cell_length_c                   31.0045(4)
_cell_measurement_reflns_used    8933
_cell_measurement_temperature    293
_cell_measurement_theta_max      75.3250
_cell_measurement_theta_min      2.8170
_cell_volume                     1150.68(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -47.00 130.00   1.00    2.00    --   41.36   0.00-180.00  177
  2  \w      2.00  97.00   1.00    2.00    --   41.36-125.00  60.00   95
  3  \w     34.00  69.00   1.00    7.93    --  110.53 -30.00  30.00   35
  4  \w     38.00  77.00   1.00    7.93    --  110.53 -45.00   0.00   39
  5  \w     28.00 109.00   1.00    7.93    --  110.53 -94.00 -30.00   81
  6  \w     38.00  77.00   1.00    7.93    --  110.53 -45.00 120.00   39
  7  \w     38.00  77.00   1.00    7.93    --  110.53 -45.00  30.00   39
  8  \w     34.00  69.00   1.00    7.93    --  110.53 -30.00-180.00   35
  9  \w     38.00  77.00   1.00    7.93    --  110.53 -45.00-150.00   39
 10  \w     28.00 109.00   1.00    7.93    --  110.53 -94.00  30.00   81
 11  \w     34.00  69.00   1.00    7.93    --  110.53 -30.00-150.00   35
 12  \w     28.00 109.00   1.00    7.93    --  110.53 -94.00-150.00   81
 13  \w     34.00  69.00   1.00    7.93    --  110.53 -30.00  60.00   35
 14  \w     85.00 158.00   1.00    7.93    --  110.53  45.00 -60.00   73
 15  \w     34.00 115.00   1.00    7.93    --  110.53-111.00-180.00   81
 16  \w   -118.00  -9.00   1.00    2.00    --  -41.36 -77.00  30.00  109
 17  \w   -118.00  -9.00   1.00    2.00    --  -41.36 -77.00 -60.00  109
 18  \w     13.00 115.00   1.00    2.00    --   41.36  57.00-150.00  102
 19  \w     82.00 158.00   1.00    7.93    --  110.53  30.00  30.00   76
 20  \w     34.00  69.00   1.00    7.93    --  110.53 -30.00-120.00   35
 21  \w     85.00 158.00   1.00    7.93    --  110.53  45.00  90.00   73
 22  \w     85.00 158.00   1.00    7.93    --  110.53  45.00-150.00   73
 23  \w     82.00 158.00   1.00    7.93    --  110.53  30.00 -90.00   76
 24  \w     81.00 158.00   1.00    7.93    --  110.53  61.00 -30.00   77
 25  \w     78.00 158.00   1.00    7.93    --  110.53  77.00 150.00   80
 26  \w     34.00  69.00   1.00    7.93    --  110.53 -30.00 -60.00   35
 27  \w     82.00 158.00   1.00    7.93    --  110.53  30.00 150.00   76
 28  \w   -118.00  -9.00   1.00    2.00    --  -41.36 -77.00 120.00  109
 29  \w   -118.00  -9.00   1.00    2.00    --  -41.36 -77.00-120.00  109
 30  \w      2.00  97.00   1.00    2.00    --   41.36-125.00-180.00   95
 31  \w     78.00 158.00   1.00    7.93    --  110.53  77.00   0.00   80
 32  \w     81.00 158.00   1.00    7.93    --  110.53  61.00 -90.00   77
 33  \w     81.00 149.00   1.00    7.93    --  110.53  61.00 -60.00   68
 34  \w     78.00 158.00   1.00    7.93    --  110.53  77.00  30.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0621207000
_diffrn_orient_matrix_UB_12      0.1519825000
_diffrn_orient_matrix_UB_13      0.0127192000
_diffrn_orient_matrix_UB_21      -0.2077291000
_diffrn_orient_matrix_UB_22      -0.0225632000
_diffrn_orient_matrix_UB_23      0.0418688000
_diffrn_orient_matrix_UB_31      0.3379648000
_diffrn_orient_matrix_UB_32      -0.0418004000
_diffrn_orient_matrix_UB_33      0.0235585000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            15079
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.568
_diffrn_reflns_theta_max         66.568
_diffrn_reflns_theta_min         2.850
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_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     173
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0534P)^2^+0.3101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1901
_reflns_number_total             2050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01851_si_002.cif
_cod_data_source_block           4b
_cod_database_code               4033080
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2017-05-15
_olex2_submission_original_sample_id 4b
_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 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.446