Catalyst-free direct regiospecific multicomponent synthesis of C3-functionalized pyrroles.
Pawar, Amol Prakash; Yadav, Jyothi; Dolas, Atul Jankiram; Iype, Eldhose; Rangan, Krishnan; Kumar, Indresh; Organic & biomolecular chemistry 20 (2022) 5747–5758; doi:10.1039/d2ob00961g

data_7158758
_publ_section_title
;
 Catalyst-free direct regiospecific multicomponent synthesis of
 C3-functionalized pyrroles.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5747
_journal_page_last               5758
_journal_paper_doi               10.1039/d2ob00961g
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_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             2021-12-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-12 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.698(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1124(2)
_cell_length_b                   11.30100(10)
_cell_length_c                   10.6161(2)
_cell_measurement_reflns_used    8423
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      79.2050
_cell_measurement_theta_min      4.2000
_cell_volume                     1255.17(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -23.00  56.00   0.50    1.00    --    0.00  57.00-180.00  158
  2  \w    -67.00  -3.00   0.50    1.00    --    0.00 -37.00  60.00  128
  3  \w    -79.00  22.00   0.50    1.00    --    0.00 -57.00-180.00  202
  4  \w    -85.00   3.00   0.50    1.00    --    0.00 -77.00   0.00  176
  5  \w     98.00 140.00   0.50    3.00    --  107.20 -82.00-150.00   84
  6  \w     85.00 140.00   0.50    3.00    --  107.20 -82.00 -30.00  110
  7  \w     35.00  71.00   0.50    3.00    --  107.20 -45.00  30.00   72
  8  \w     31.00  56.00   0.50    3.00    --  107.20 -82.00  60.00   50
  9  \w     41.00  67.00   0.50    3.00    --  107.20 -82.00-150.00   52
 10  \w     63.00 120.00   0.50    3.00    --  107.20 -82.00  60.00  114
 11  \w     49.00 134.00   0.50    3.00    --  107.20 -82.00 -90.00  170
 12  \w     99.00 193.00   0.50    3.00    --  107.20  45.00  30.00  188
 13  \w     19.00 128.00   0.50    3.00    --  107.20 -61.00 -90.00  218
 14  \w     90.00 126.00   0.50    3.00    --  107.20  30.00 150.00   72
 15  \w     20.00  54.00   0.50    3.00    --  107.20 -82.00  90.00   68
 16  \w    136.00 197.00   0.50    3.00    --  107.20  30.00 -60.00  122
 17  \w    160.00 186.00   0.50    3.00    --  107.20  30.00 150.00   52
 18  \w    104.00 139.00   0.50    3.00    --  107.20 -82.00  90.00   70
 19  \w     18.00  51.00   0.50    3.00    --  107.20 -61.00  90.00   66
 20  \w     75.00 111.00   0.50    3.00    --  107.20 -61.00  90.00   72
 21  \w     39.00  65.00   0.50    3.00    --  107.20 -77.00-150.00   52
 22  \w     90.00 124.00   0.50    3.00    --  107.20  30.00 -60.00   68
 23  \w     75.00 105.00   0.50    3.00    --  107.20 -45.00  30.00   60
 24  \w    100.00 131.00   0.50    3.00    --  107.20 -82.00 150.00   62
 25  \w    102.00 163.00   0.50    3.00    --  107.20  30.00 -30.00  122
 26  \w    168.00 197.00   0.50    3.00    --  107.20  30.00 -30.00   58
 27  \w     55.00 137.00   0.50    3.00    --  107.20 -82.00 120.00  164
 28  \w     91.00 195.00   0.50    3.00    --  107.20  52.00   8.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): 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      0.1271900000
_diffrn_orient_matrix_UB_12      -0.0378297000
_diffrn_orient_matrix_UB_13      0.1057065000
_diffrn_orient_matrix_UB_21      0.0735339000
_diffrn_orient_matrix_UB_22      0.0782264000
_diffrn_orient_matrix_UB_23      -0.0681243000
_diffrn_orient_matrix_UB_31      -0.0089757000
_diffrn_orient_matrix_UB_32      0.1051383000
_diffrn_orient_matrix_UB_33      0.0890452000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13555
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.618
_diffrn_reflns_theta_min         4.226
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0401P)^2^+0.5742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2498
_reflns_number_total             2695
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00961g2.cif
_cod_data_source_block           exp_968_ik_apis-cp_autored
_cod_depositor_comments          'Adding full bibliography for 7158758.cif.'
_cod_database_code               7158758
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H14 N2 O2'
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.867
_reflns_odcompleteness_completeness 100.00
_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 Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              6679
_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 1.848
_oxdiff_exptl_absorpt_empirical_full_min 0.681