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_7127573
_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         'C16 H18 N2 O2'
_chemical_formula_sum            'C16 H18 N2 O2'
_chemical_formula_weight         270.32
_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'
_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                 102.324(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8918(2)
_cell_length_b                   10.9673(2)
_cell_length_c                   11.9061(3)
_cell_measurement_reflns_used    4826
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.4160
_cell_measurement_theta_min      5.5070
_cell_volume                     1389.45(5)
_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 0.968
_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     17.00  45.00   0.50    1.92    --    0.00  57.00  60.00   56
  2  \w    -19.00  89.00   0.50    1.92    --    0.00  37.00-150.00  216
  3  \w    -31.00  -5.00   0.50    1.92    --    0.00 -57.00 -30.00   52
  4  \w    -88.00 -56.00   0.50    1.92    --    0.00 -57.00 -30.00   64
  5  \w     98.00 134.00   0.50    7.68    --  107.20 -15.00  30.00   72
  6  \w    105.00 194.00   0.50    7.68    --  107.20  45.00   0.00  178
  7  \w     19.00 115.00   0.50    7.68    --  107.20 -45.00  90.00  192
  8  \w     19.00  63.00   0.50    7.68    --  107.20 -15.00  30.00   88
  9  \w     24.00  81.00   0.50    7.68    --  107.20 -30.00-120.00  114
 10  \w     36.00 119.00   0.50    7.68    --  107.20 -61.00  90.00  166
 11  \w     18.00  45.00   0.50    7.68    --  107.20 -30.00 -60.00   54
 12  \w     80.00 105.00   0.50    7.68    --  107.20 -30.00 -60.00   50
 13  \w     94.00 138.00   0.50    7.68    --  107.20 -77.00-120.00   88
 14  \w     30.00  89.00   0.50    7.68    --  107.20 -77.00-120.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0926075000
_diffrn_orient_matrix_UB_12      -0.0370575000
_diffrn_orient_matrix_UB_13      0.0753240000
_diffrn_orient_matrix_UB_21      0.0843607000
_diffrn_orient_matrix_UB_22      0.0625470000
_diffrn_orient_matrix_UB_23      0.1043654000
_diffrn_orient_matrix_UB_31      -0.0724995000
_diffrn_orient_matrix_UB_32      0.1202494000
_diffrn_orient_matrix_UB_33      -0.0311843000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7404
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.954
_diffrn_reflns_theta_min         4.155
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76828
_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            Red
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and Hexane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0542P)^2^+0.6332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2675
_reflns_number_total             2934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06357f2.cif
_cod_data_source_block           exp_518_indresh-01
_cod_depositor_comments
'Adding full bibliography for 7127572--7127574.cif.'
_cod_database_code               7127573
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.90
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C2(H2A), C10(H10), C12(H12), C11(H11), C3(H3)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
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 1.605
_oxdiff_exptl_absorpt_empirical_full_min 0.817