Direct catalytic synthesis of β-(C3)-substituted pyrroles: a complementary addition to the Paal-Knorr reaction.
Pawar, Amol Prakash; Yadav, Jyothi; Mir, Nisar Ahmad; Iype, Eldhose; Rangan, Krishnan; Anthal, Sumati; Kant, Rajni; Kumar, Indresh; Chemical communications (Cambridge, England) 57 (2021) 251–254; doi:10.1039/d0cc06357f

data_7127574
_publ_section_title
;
 Direct catalytic synthesis of \b-(C3)-substituted pyrroles: a
 complementary addition to the Paal-Knorr reaction.
;
_journal_issue                   2
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              251
_journal_page_last               254
_journal_paper_doi               10.1039/d0cc06357f
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-20 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.460(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2879(2)
_cell_length_b                   7.27320(10)
_cell_length_c                   19.0032(3)
_cell_measurement_reflns_used    5180
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.2800
_cell_measurement_theta_min      7.2710
_cell_volume                     1517.29(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (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      93(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.957
_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     12.00  65.00   0.50    1.89    --    0.00  77.00  90.00  106
  2  \w    -19.00  37.00   0.50    1.89    --    0.00  37.00-150.00  112
  3  \w    -50.00  32.00   0.50    1.89    --    0.00 -82.00   0.00  164
  4  \w     44.00  86.00   0.50    1.89    --    0.00  37.00-150.00   84
  5  \w     24.00 115.00   0.50    7.56    --  107.20 -30.00-120.00  182
  6  \w     24.00  89.00   0.50    7.56    --  107.20 -45.00  30.00  130
  7  \w     21.00 125.00   0.50    7.56    --  107.20 -30.00  30.00  208
  8  \w     95.00 166.00   0.50    7.56    --  107.20  30.00 150.00  142
  9  \w     25.00  91.00   0.50    7.56    --  107.20 -45.00-120.00  132
 10  \w    171.00 196.00   0.50    7.56    --  107.20  30.00 -60.00   50
 11  \w     83.00 195.00   0.50    7.56    --  107.20  61.00   0.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0594237000
_diffrn_orient_matrix_UB_12      0.0715754000
_diffrn_orient_matrix_UB_13      -0.0598859000
_diffrn_orient_matrix_UB_21      0.1126954000
_diffrn_orient_matrix_UB_22      -0.1201239000
_diffrn_orient_matrix_UB_23      0.0299018000
_diffrn_orient_matrix_UB_31      -0.0586145000
_diffrn_orient_matrix_UB_32      -0.1592354000
_diffrn_orient_matrix_UB_33      -0.0497169000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7899
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.382
_diffrn_reflns_theta_min         4.178
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       Block
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and Hexane'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0539P)^2^+0.5825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2906
_reflns_number_total             3183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06357f2.cif
_cod_data_source_block           exp_534_indresh-ap-ch2ph-fr-nh
_cod_depositor_comments
'Adding full bibliography for 7127572--7127574.cif.'
_cod_database_code               7127574
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), C12(H12), C10(H10), C15(H15), C16(H16), C17(H17), C19(H19), C11(H11),
  C18(H18), C5(H5), C2(H2B), C4(H4), C3(H3)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.781