#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/75/7127572.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7127572
loop_
_publ_author_name
'Pawar, Amol Prakash'
'Yadav, Jyothi'
'Mir, Nisar Ahmad'
'Iype, Eldhose'
'Rangan, Krishnan'
'Anthal, Sumati'
'Kant, Rajni'
'Kumar, Indresh'
_publ_section_title
;
 Direct catalytic synthesis of β-(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         'C20 H18 N2 O3'
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_audit_update_record
;
2018-02-26 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.880(14)
_cell_angle_beta                 110.076(16)
_cell_angle_gamma                114.477(14)
_cell_formula_units_Z            2
_cell_length_a                   8.5337(13)
_cell_length_b                   10.2008(13)
_cell_length_c                   11.672(2)
_cell_measurement_reflns_used    1519
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.2050
_cell_measurement_theta_min      4.0010
_cell_volume                     853.7(3)
_computing_cell_refinement       'CrysAlisPro,Oxford Diff.Ltd,Ver 1.171.34.40'
_computing_data_collection       'CrysAlisPro,Oxford Diff.Ltd,Ver 1.171.34.40'
_computing_data_reduction        'CrysAlisPro,Oxford Diff.Ltd,Ver 1.171.34.40'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'PLATON(Spek,2009)& PARST(Nardelli,1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1049
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0900
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5456
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'crys Alis RED'
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       0.0136(15)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.616
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.616
_refine_ls_R_factor_all          0.1945
_refine_ls_R_factor_gt           0.1639
_refine_ls_shift/su_max          0.886
_refine_ls_shift/su_mean         0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4595
_refine_ls_wR_factor_ref         0.4779
_reflns_number_gt                1859
_reflns_number_total             2988
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc06357f2.cif
_cod_data_source_block           fisk-09re
_cod_depositor_comments
'Adding full bibliography for 7127572--7127574.cif.'
_cod_original_cell_volume        853.7(2)
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               7127572
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C20 C -0.519(4) 0.844(3) -0.599(4) 0.45(4) Uani 1 1 d . . .
H20A H -0.4141 0.9021 -0.6194 0.675 Uiso 1 1 calc R . .
H20B H -0.5341 0.9057 -0.5446 0.675 Uiso 1 1 calc R . .
H20C H -0.6297 0.8009 -0.6735 0.675 Uiso 1 1 calc R . .
O2 O 0.2772(6) 0.4330(5) 0.0475(4) 0.0521(14) Uani 1 1 d . . .
H2 H 0.3781 0.4943 0.0495 0.078 Uiso 1 1 calc R . .
O1 O 0.3985(7) 0.3038(6) -0.1171(5) 0.0586(15) Uani 1 1 d . . .
N2 N 0.0104(8) 0.5719(7) -0.2981(5) 0.0516(16) Uani 1 1 d . . .
N1 N 0.1072(8) 0.1227(6) -0.1578(5) 0.0489(15) Uani 1 1 d . . .
C8 C 0.1619(8) 0.3565(7) -0.0759(6) 0.0426(16) Uani 1 1 d . . .
C6 C -0.0485(9) 0.1058(8) -0.1324(7) 0.0480(17) Uani 1 1 d . . .
C7 C 0.2443(9) 0.2640(7) -0.1176(6) 0.0437(16) Uani 1 1 d . . .
C14 C -0.1219(10) 0.6200(8) -0.3697(6) 0.0486(17) Uani 1 1 d . . .
C10 C 0.1377(9) 0.4562(7) -0.1659(6) 0.0451(16) Uani 1 1 d . . .
C5 C -0.2085(10) -0.0227(8) -0.1495(7) 0.0580(19) Uani 1 1 d . . .
H5 H -0.2244 -0.1130 -0.1826 0.070 Uiso 1 1 calc R . .
C11 C -0.0249(9) 0.4631(8) -0.2297(6) 0.0485(17) Uani 1 1 d . . .
H11 H -0.1404 0.4039 -0.2272 0.058 Uiso 1 1 calc R . .
C15 C -0.2576(10) 0.6174(9) -0.3289(7) 0.058(2) Uani 1 1 d . . .
H15 H -0.2643 0.5820 -0.2570 0.069 Uiso 1 1 calc R . .
C12 C 0.1945(10) 0.6334(9) -0.2784(7) 0.057(2) Uani 1 1 d . . .
H12 H 0.2539 0.7096 -0.3142 0.069 Uiso 1 1 calc R . .
C9 C 0.1258(12) 0.0036(9) -0.2135(9) 0.066(2) Uani 1 1 d . . .
H9A H 0.2479 0.0401 -0.2157 0.100 Uiso 1 1 calc R . .
H9B H 0.0334 -0.0350 -0.2965 0.100 Uiso 1 1 calc R . .
H9C H 0.1083 -0.0726 -0.1651 0.100 Uiso 1 1 calc R . .
C1 C -0.0217(9) 0.2401(7) -0.0798(6) 0.0423(16) Uani 1 1 d . . .
C16 C -0.3829(12) 0.6679(10) -0.3959(8) 0.066(2) Uani 1 1 d . . .
H16 H -0.4737 0.6663 -0.3683 0.079 Uiso 1 1 calc R . .
C2 C -0.1535(9) 0.2496(8) -0.0440(7) 0.0513(18) Uani 1 1 d . . .
H2A H -0.1356 0.3396 -0.0087 0.062 Uiso 1 1 calc R . .
C13 C 0.2776(10) 0.5649(8) -0.1974(8) 0.0570(19) Uani 1 1 d . . .
H13 H 0.4030 0.5857 -0.1682 0.068 Uiso 1 1 calc R . .
C4 C -0.3409(11) -0.0108(10) -0.1159(8) 0.070(2) Uani 1 1 d . . .
H4 H -0.4514 -0.0942 -0.1300 0.084 Uiso 1 1 calc R . .
C19 C -0.1204(12) 0.6677(10) -0.4795(8) 0.068(2) Uani 1 1 d . . .
H19 H -0.0369 0.6634 -0.5119 0.082 Uiso 1 1 calc R . .
C17 C -0.3754(13) 0.7203(10) -0.5024(9) 0.073(2) Uani 1 1 d . . .
C18 C -0.2423(13) 0.7213(11) -0.5400(9) 0.079(3) Uani 1 1 d . . .
H18 H -0.2332 0.7602 -0.6103 0.094 Uiso 1 1 calc R . .
O3 O -0.4993(12) 0.7709(11) -0.5597(10) 0.131(3) Uani 1 1 d . . .
C3 C -0.3155(10) 0.1227(9) -0.0610(8) 0.060(2) Uani 1 1 d . . .
H3 H -0.4059 0.1272 -0.0360 0.072 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C20 H20A 109.4 . . ?
O3 C20 H20B 108.9 . . ?
H20A C20 H20B 109.7 . . ?
O3 C20 H20C 109.7 . . ?
H20A C20 H20C 109.7 . . ?
H20B C20 H20C 109.4 . . ?
C8 O2 H2 109.5 . . ?
C12 N2 C11 108.6(5) . . ?
C12 N2 C14 126.0(6) . . ?
C11 N2 C14 125.2(6) . . ?
C7 N1 C6 111.4(5) . . ?
C7 N1 C9 124.0(6) . . ?
C6 N1 C9 124.6(6) . . ?
O2 C8 C10 112.9(5) . . ?
O2 C8 C1 109.9(5) . . ?
C10 C8 C1 112.5(5) . . ?
O2 C8 C7 109.9(5) . . ?
C10 C8 C7 109.1(5) . . ?
C1 C8 C7 102.0(5) . . ?
C1 C6 C5 121.5(6) . . ?
C1 C6 N1 110.0(6) . . ?
C5 C6 N1 128.4(6) . . ?
O1 C7 N1 124.4(6) . . ?
O1 C7 C8 128.4(6) . . ?
N1 C7 C8 107.3(5) . . ?
C19 C14 C15 118.7(7) . . ?
C19 C14 N2 122.0(6) . . ?
C15 C14 N2 119.3(6) . . ?
C11 C10 C13 106.8(6) . . ?
C11 C10 C8 125.7(6) . . ?
C13 C10 C8 127.4(6) . . ?
C4 C5 C6 117.3(7) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C10 C11 N2 108.6(6) . . ?
C10 C11 H11 125.7 . . ?
N2 C11 H11 125.7 . . ?
C16 C15 C14 119.6(8) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
N2 C12 C13 108.7(6) . . ?
N2 C12 H12 125.7 . . ?
C13 C12 H12 125.7 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C1 C6 120.3(6) . . ?
C2 C1 C8 131.1(6) . . ?
C6 C1 C8 108.5(5) . . ?
C17 C16 C15 121.0(8) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C1 C2 C3 119.2(7) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C12 C13 C10 107.3(6) . . ?
C12 C13 H13 126.4 . . ?
C10 C13 H13 126.4 . . ?
C5 C4 C3 122.0(7) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C18 C19 C14 119.5(8) . . ?
C18 C19 H19 120.3 . . ?
C14 C19 H19 120.3 . . ?
C18 C17 O3 124.9(9) . . ?
C18 C17 C16 118.1(8) . . ?
O3 C17 C16 117.0(9) . . ?
C17 C18 C19 122.9(8) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C20 O3 C17 147(3) . . ?
C4 C3 C2 119.5(7) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C20 O3 0.93(2) . ?
C20 H20A 0.9591 . ?
C20 H20B 0.9591 . ?
C20 H20C 0.9590 . ?
O2 C8 1.417(8) . ?
O2 H2 0.8200 . ?
O1 C7 1.204(7) . ?
N2 C12 1.358(9) . ?
N2 C11 1.370(8) . ?
N2 C14 1.427(9) . ?
N1 C7 1.367(9) . ?
N1 C6 1.401(8) . ?
N1 C9 1.461(9) . ?
C8 C10 1.496(9) . ?
C8 C1 1.508(9) . ?
C8 C7 1.547(9) . ?
C6 C1 1.387(10) . ?
C6 C5 1.395(10) . ?
C14 C19 1.380(11) . ?
C14 C15 1.386(10) . ?
C10 C11 1.363(9) . ?
C10 C13 1.417(9) . ?
C5 C4 1.364(10) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C15 C16 1.384(10) . ?
C15 H15 0.9300 . ?
C12 C13 1.362(10) . ?
C12 H12 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C1 C2 1.364(9) . ?
C16 C17 1.372(13) . ?
C16 H16 0.9300 . ?
C2 C3 1.395(10) . ?
C2 H2A 0.9300 . ?
C13 H13 0.9300 . ?
C4 C3 1.395(11) . ?
C4 H4 0.9300 . ?
C19 C18 1.363(11) . ?
C19 H19 0.9300 . ?
C17 C18 1.347(12) . ?
C17 O3 1.345(10) . ?
C18 H18 0.9300 . ?
C3 H3 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C6 C1 3.3(8) . . . . ?
C9 N1 C6 C1 -179.9(7) . . . . ?
C7 N1 C6 C5 -174.2(7) . . . . ?
C9 N1 C6 C5 2.6(12) . . . . ?
C6 N1 C7 O1 172.2(6) . . . . ?
C9 N1 C7 O1 -4.6(11) . . . . ?
C6 N1 C7 C8 -8.0(7) . . . . ?
C9 N1 C7 C8 175.2(6) . . . . ?
O2 C8 C7 O1 -54.6(8) . . . . ?
C10 C8 C7 O1 69.7(8) . . . . ?
C1 C8 C7 O1 -171.1(6) . . . . ?
O2 C8 C7 N1 125.7(5) . . . . ?
C10 C8 C7 N1 -110.1(6) . . . . ?
C1 C8 C7 N1 9.1(7) . . . . ?
C12 N2 C14 C19 39.5(11) . . . . ?
C11 N2 C14 C19 -146.1(8) . . . . ?
C12 N2 C14 C15 -141.2(8) . . . . ?
C11 N2 C14 C15 33.1(10) . . . . ?
O2 C8 C10 C11 -113.6(7) . . . . ?
C1 C8 C10 C11 11.4(9) . . . . ?
C7 C8 C10 C11 123.9(7) . . . . ?
O2 C8 C10 C13 63.3(9) . . . . ?
C1 C8 C10 C13 -171.7(6) . . . . ?
C7 C8 C10 C13 -59.2(9) . . . . ?
C1 C6 C5 C4 1.9(11) . . . . ?
N1 C6 C5 C4 179.2(7) . . . . ?
C13 C10 C11 N2 -0.3(8) . . . . ?
C8 C10 C11 N2 177.2(6) . . . . ?
C12 N2 C11 C10 0.3(8) . . . . ?
C14 N2 C11 C10 -174.9(6) . . . . ?
C19 C14 C15 C16 -2.6(11) . . . . ?
N2 C14 C15 C16 178.1(7) . . . . ?
C11 N2 C12 C13 -0.2(8) . . . . ?
C14 N2 C12 C13 175.0(7) . . . . ?
C5 C6 C1 C2 -0.4(11) . . . . ?
N1 C6 C1 C2 -178.2(6) . . . . ?
C5 C6 C1 C8 -179.2(6) . . . . ?
N1 C6 C1 C8 3.0(8) . . . . ?
O2 C8 C1 C2 57.5(9) . . . . ?
C10 C8 C1 C2 -69.1(9) . . . . ?
C7 C8 C1 C2 174.1(7) . . . . ?
O2 C8 C1 C6 -123.8(6) . . . . ?
C10 C8 C1 C6 109.5(6) . . . . ?
C7 C8 C1 C6 -7.3(7) . . . . ?
C14 C15 C16 C17 0.2(12) . . . . ?
C6 C1 C2 C3 -0.1(10) . . . . ?
C8 C1 C2 C3 178.5(7) . . . . ?
N2 C12 C13 C10 0.0(9) . . . . ?
C11 C10 C13 C12 0.2(9) . . . . ?
C8 C10 C13 C12 -177.2(7) . . . . ?
C6 C5 C4 C3 -3.0(12) . . . . ?
C15 C14 C19 C18 4.9(13) . . . . ?
N2 C14 C19 C18 -175.8(7) . . . . ?
C15 C16 C17 C18 0.0(13) . . . . ?
C15 C16 C17 O3 -178.2(8) . . . . ?
O3 C17 C18 C19 -179.5(10) . . . . ?
C16 C17 C18 C19 2.5(15) . . . . ?
C14 C19 C18 C17 -5.0(15) . . . . ?
C18 C17 O3 C20 -42(5) . . . . ?
C16 C17 O3 C20 136(5) . . . . ?
C5 C4 C3 C2 2.6(13) . . . . ?
C1 C2 C3 C4 -1.0(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168352403
