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#$Date: 2025-04-05 05:43:15 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298869 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/97/7249754.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_7249754
loop_
_publ_author_name
'Nagdeve, Rahul D.'
'Thakur, Jyoti Swarup'
'Chandrashekharappa, Sandeep'
'Mondal, Pradip Kumar'
'Deb, Pran Kishore'
'Polentarutti, Maurizio'
'Bairagi, Keshab M.'
'Rakshit, Gourav'
'Alwassil, Osama I.'
'Pillay, Melendhran'
'Venugopala, Katharigatta N.'
'Nayak, Susanta K.'
_publ_section_title
;
 Structural analysis, in vitro anti-tubercular activities, and in silico
 ADMET evaluation of ethyl 7-methoxy-3-(4-substituted
 benzoyl)indolizine-1-carboxylates
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1707
_journal_page_last               1721
_journal_paper_doi               10.1039/D4CE01018C
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36
_chemical_melting_point          125
_chemical_name_common            Indolizine
_chemical_name_systematic
;
ethyl 7-methoxy-3-(4-methylbenzoyl)indolizine-1-carboxylate
;
_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   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-12-01 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.52(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.930(2)
_cell_length_b                   7.6700(15)
_cell_length_c                   21.320(4)
_cell_measurement_reflns_used    41143
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.7
_cell_measurement_theta_min      2.8
_cell_volume                     1622.2(5)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'Elettra Synchrotron - XRD1 BL'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Huber Kappa Goniometer, Pilatus 2M detector'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0088
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            41143
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.745
_diffrn_reflns_theta_min         2.780
_diffrn_source                   Synchrotron
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      1.38
_exptl_crystal_description       cube
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.072(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0359
_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/[σ²(Fo²)+(0.0643P)²+0.3606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4685
_reflns_number_total             4760
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01018c2.cif
_cod_data_source_block           5b
_cod_depositor_comments
'Adding full bibliography for 7249753--7249759.cif.'
_cod_original_cell_volume        1622.2(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249754
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.991
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.30600(5) 0.16674(7) 0.51522(2) 0.01719(12) Uani 1 1 d . . . . .
O4 O 0.58230(5) 0.48398(8) 0.67251(2) 0.01926(13) Uani 1 1 d . . . . .
O1 O 0.31506(6) 0.07602(8) 0.41494(3) 0.02095(13) Uani 1 1 d . . . . .
O3 O 0.94733(5) 0.35156(8) 0.43295(3) 0.02098(13) Uani 1 1 d . . . . .
N1 N 0.69882(6) 0.34982(8) 0.49630(3) 0.01403(13) Uani 1 1 d . . . . .
C4 C 0.53448(7) 0.35032(9) 0.57584(3) 0.01537(14) Uani 1 1 d . . . . .
H4 H 0.4456(12) 0.3196(15) 0.5888(6) 0.022(3) Uiso 1 1 d . . . . .
C7 C 0.36965(7) 0.14362(9) 0.46108(3) 0.01534(14) Uani 1 1 d . . . . .
C3 C 0.62470(7) 0.44040(9) 0.61483(3) 0.01555(14) Uani 1 1 d . . . . .
C2 C 0.75363(7) 0.48458(10) 0.59412(3) 0.01661(14) Uani 1 1 d . . . . .
H2 H 0.8189(12) 0.5480(15) 0.6195(5) 0.022(3) Uiso 1 1 d . . . . .
C12 C 0.71435(7) 0.29518(9) 0.43378(3) 0.01458(14) Uani 1 1 d . . . . .
C5 C 0.57180(7) 0.30300(9) 0.51540(3) 0.01415(14) Uani 1 1 d . . . . .
C10 C 0.59642(7) 0.20555(9) 0.41499(3) 0.01458(14) Uani 1 1 d . . . . .
C6 C 0.50685(7) 0.21232(9) 0.46443(3) 0.01454(14) Uani 1 1 d . . . . .
C8 C 0.16662(7) 0.10972(10) 0.51365(4) 0.01851(15) Uani 1 1 d . . . . .
H8A H 0.1655(11) -0.0178(16) 0.5065(5) 0.021(3) Uiso 1 1 d . . . . .
H8B H 0.1185(12) 0.1648(15) 0.4788(6) 0.022(3) Uiso 1 1 d . . . . .
C13 C 0.83968(7) 0.32196(9) 0.40299(3) 0.01526(14) Uani 1 1 d . . . . .
C1 C 0.78778(7) 0.43913(9) 0.53510(3) 0.01587(14) Uani 1 1 d . . . . .
H1 H 0.8724(12) 0.4620(16) 0.5189(6) 0.024(3) Uiso 1 1 d . . . . .
C15 C 0.74105(7) 0.40335(10) 0.29591(3) 0.01777(14) Uani 1 1 d . . . . .
H15 H 0.6622(12) 0.4575(16) 0.3149(6) 0.025(3) Uiso 1 1 d . . . . .
C14 C 0.84148(7) 0.32050(9) 0.33291(3) 0.01531(14) Uani 1 1 d . . . . .
C16 C 0.75150(8) 0.41080(10) 0.23100(4) 0.02039(15) Uani 1 1 d . . . . .
H16 H 0.6819(13) 0.4664(18) 0.2052(6) 0.031(3) Uiso 1 1 d . . . . .
C19 C 0.95216(7) 0.24587(10) 0.30468(4) 0.01839(15) Uani 1 1 d . . . . .
H19 H 1.0224(13) 0.1883(17) 0.3320(6) 0.027(3) Uiso 1 1 d . . . . .
C17 C 0.86060(8) 0.33432(11) 0.20293(4) 0.02187(16) Uani 1 1 d . . . . .
H17 H 0.8643(13) 0.3400(17) 0.1568(6) 0.029(3) Uiso 1 1 d . . . . .
C20 C 0.67145(8) 0.58873(11) 0.71165(4) 0.02122(16) Uani 1 1 d . . . . .
H20A H 0.7535(12) 0.5219(16) 0.7264(6) 0.025(3) Uiso 1 1 d . . . . .
H20B H 0.6167(13) 0.6195(17) 0.7483(6) 0.028(3) Uiso 1 1 d . . . . .
H20C H 0.6994(12) 0.6899(16) 0.6888(6) 0.023(3) Uiso 1 1 d . . . . .
C11 C 0.57481(7) 0.10226(10) 0.35590(3) 0.01742(14) Uani 1 1 d . . . . .
H11A H 0.5190(13) 0.1651(17) 0.3247(6) 0.029(3) Uiso 1 1 d . . . . .
H11B H 0.5247(12) -0.0063(17) 0.3646(6) 0.027(3) Uiso 1 1 d . . . . .
H11C H 0.6610(13) 0.0749(16) 0.3380(6) 0.028(3) Uiso 1 1 d . . . . .
C18 C 0.96077(8) 0.25104(11) 0.23970(4) 0.02182(16) Uani 1 1 d . . . . .
H18 H 1.0392(13) 0.1941(17) 0.2206(6) 0.028(3) Uiso 1 1 d . . . . .
C9 C 0.11029(8) 0.15844(12) 0.57575(4) 0.02476(17) Uani 1 1 d . . . . .
H9A H 0.1102(14) 0.2833(19) 0.5823(6) 0.035(3) Uiso 1 1 d . . . . .
H9B H 0.1606(15) 0.1028(19) 0.6115(7) 0.040(4) Uiso 1 1 d . . . . .
H9C H 0.0157(15) 0.118(2) 0.5760(7) 0.041(4) Uiso 1 1 d . . . . .
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 0.0064 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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
C7 O2 C8 114.98(6) . . ?
C3 O4 C20 117.13(6) . . ?
C1 N1 C5 121.52(6) . . ?
C1 N1 C12 128.70(6) . . ?
C5 N1 C12 109.76(6) . . ?
C3 C4 C5 119.44(7) . . ?
C3 C4 H4 121.8(7) . . ?
C5 C4 H4 118.7(7) . . ?
O1 C7 O2 122.50(7) . . ?
O1 C7 C6 125.07(7) . . ?
O2 C7 C6 112.41(6) . . ?
O4 C3 C4 116.70(7) . . ?
O4 C3 C2 122.99(7) . . ?
C4 C3 C2 120.31(7) . . ?
C1 C2 C3 119.51(7) . . ?
C1 C2 H2 117.5(7) . . ?
C3 C2 H2 123.0(7) . . ?
C10 C12 N1 106.91(6) . . ?
C10 C12 C13 131.66(6) . . ?
N1 C12 C13 121.19(6) . . ?
N1 C5 C4 118.80(7) . . ?
N1 C5 C6 106.84(6) . . ?
C4 C5 C6 134.36(6) . . ?
C12 C10 C6 108.37(6) . . ?
C12 C10 C11 126.00(6) . . ?
C6 C10 C11 125.27(6) . . ?
C10 C6 C5 108.04(6) . . ?
C10 C6 C7 124.64(6) . . ?
C5 C6 C7 127.27(7) . . ?
O2 C8 C9 107.21(7) . . ?
O2 C8 H8A 107.8(7) . . ?
C9 C8 H8A 112.2(7) . . ?
O2 C8 H8B 109.0(7) . . ?
C9 C8 H8B 112.3(7) . . ?
H8A C8 H8B 108.2(10) . . ?
O3 C13 C12 122.05(7) . . ?
O3 C13 C14 117.87(7) . . ?
C12 C13 C14 120.05(6) . . ?
C2 C1 N1 120.42(7) . . ?
C2 C1 H1 123.8(8) . . ?
N1 C1 H1 115.8(8) . . ?
C16 C15 C14 119.80(7) . . ?
C16 C15 H15 119.0(7) . . ?
C14 C15 H15 121.2(7) . . ?
C15 C14 C19 119.88(7) . . ?
C15 C14 C13 121.42(7) . . ?
C19 C14 C13 118.51(7) . . ?
C17 C16 C15 120.24(7) . . ?
C17 C16 H16 119.6(8) . . ?
C15 C16 H16 120.1(8) . . ?
C18 C19 C14 120.03(7) . . ?
C18 C19 H19 121.6(7) . . ?
C14 C19 H19 118.4(7) . . ?
C16 C17 C18 120.10(7) . . ?
C16 C17 H17 118.3(8) . . ?
C18 C17 H17 121.6(8) . . ?
O4 C20 H20A 111.6(7) . . ?
O4 C20 H20B 104.1(7) . . ?
H20A C20 H20B 109.7(10) . . ?
O4 C20 H20C 109.9(7) . . ?
H20A C20 H20C 108.9(10) . . ?
H20B C20 H20C 112.6(10) . . ?
C10 C11 H11A 111.7(8) . . ?
C10 C11 H11B 110.0(7) . . ?
H11A C11 H11B 105.5(11) . . ?
C10 C11 H11C 110.3(8) . . ?
H11A C11 H11C 108.8(11) . . ?
H11B C11 H11C 110.4(10) . . ?
C19 C18 C17 119.94(7) . . ?
C19 C18 H18 118.6(7) . . ?
C17 C18 H18 121.5(7) . . ?
C8 C9 H9A 112.0(8) . . ?
C8 C9 H9B 112.1(9) . . ?
H9A C9 H9B 108.6(12) . . ?
C8 C9 H9C 108.4(9) . . ?
H9A C9 H9C 107.8(12) . . ?
H9B C9 H9C 107.8(12) . . ?
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
O2 C7 1.3518(9) . ?
O2 C8 1.4505(9) . ?
O4 C3 1.3590(9) . ?
O4 C20 1.4355(10) . ?
O1 C7 1.2179(9) . ?
O3 C13 1.2418(9) . ?
N1 C1 1.3673(9) . ?
N1 C5 1.3896(9) . ?
N1 C12 1.4122(9) . ?
C4 C3 1.3803(10) . ?
C4 C5 1.4041(10) . ?
C4 H4 0.965(12) . ?
C7 C6 1.4596(10) . ?
C3 C2 1.4137(10) . ?
C2 C1 1.3628(10) . ?
C2 H2 0.958(12) . ?
C12 C10 1.4011(10) . ?
C12 C13 1.4470(10) . ?
C5 C6 1.4208(10) . ?
C10 C6 1.4098(10) . ?
C10 C11 1.4957(10) . ?
C8 C9 1.5069(12) . ?
C8 H8A 0.990(12) . ?
C8 H8B 0.964(12) . ?
C13 C14 1.4949(10) . ?
C1 H1 0.939(12) . ?
C15 C16 1.3936(10) . ?
C15 C14 1.3970(10) . ?
C15 H15 0.989(12) . ?
C14 C19 1.3985(10) . ?
C16 C17 1.3903(12) . ?
C16 H16 0.963(13) . ?
C19 C18 1.3923(11) . ?
C19 H19 0.992(13) . ?
C17 C18 1.3940(12) . ?
C17 H17 0.987(13) . ?
C20 H20A 1.002(12) . ?
C20 H20B 1.000(13) . ?
C20 H20C 0.963(12) . ?
C11 H11A 0.974(13) . ?
C11 H11B 0.992(13) . ?
C11 H11C 0.975(13) . ?
C18 H18 0.996(13) . ?
C9 H9A 0.968(15) . ?
C9 H9B 0.989(15) . ?
C9 H9C 0.990(15) . ?
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
C8 O2 C7 O1 -1.74(10) . . . . ?
C8 O2 C7 C6 176.76(6) . . . . ?
C20 O4 C3 C4 -175.52(6) . . . . ?
C20 O4 C3 C2 3.89(10) . . . . ?
C5 C4 C3 O4 179.39(6) . . . . ?
C5 C4 C3 C2 -0.04(10) . . . . ?
O4 C3 C2 C1 -178.72(7) . . . . ?
C4 C3 C2 C1 0.67(11) . . . . ?
C1 N1 C12 C10 178.77(7) . . . . ?
C5 N1 C12 C10 -2.74(8) . . . . ?
C1 N1 C12 C13 3.82(11) . . . . ?
C5 N1 C12 C13 -177.69(6) . . . . ?
C1 N1 C5 C4 0.52(10) . . . . ?
C12 N1 C5 C4 -178.10(6) . . . . ?
C1 N1 C5 C6 -179.73(6) . . . . ?
C12 N1 C5 C6 1.65(7) . . . . ?
C3 C4 C5 N1 -0.54(10) . . . . ?
C3 C4 C5 C6 179.80(7) . . . . ?
N1 C12 C10 C6 2.73(8) . . . . ?
C13 C12 C10 C6 176.95(7) . . . . ?
N1 C12 C10 C11 -170.64(6) . . . . ?
C13 C12 C10 C11 3.58(12) . . . . ?
C12 C10 C6 C5 -1.77(8) . . . . ?
C11 C10 C6 C5 171.66(6) . . . . ?
C12 C10 C6 C7 175.70(6) . . . . ?
C11 C10 C6 C7 -10.87(11) . . . . ?
N1 C5 C6 C10 0.07(7) . . . . ?
C4 C5 C6 C10 179.76(7) . . . . ?
N1 C5 C6 C7 -177.31(6) . . . . ?
C4 C5 C6 C7 2.38(13) . . . . ?
O1 C7 C6 C10 -1.76(11) . . . . ?
O2 C7 C6 C10 179.78(6) . . . . ?
O1 C7 C6 C5 175.21(7) . . . . ?
O2 C7 C6 C5 -3.24(10) . . . . ?
C7 O2 C8 C9 -175.68(6) . . . . ?
C10 C12 C13 O3 -154.96(8) . . . . ?
N1 C12 C13 O3 18.57(11) . . . . ?
C10 C12 C13 C14 27.14(11) . . . . ?
N1 C12 C13 C14 -159.33(6) . . . . ?
C3 C2 C1 N1 -0.70(11) . . . . ?
C5 N1 C1 C2 0.10(10) . . . . ?
C12 N1 C1 C2 178.44(7) . . . . ?
C16 C15 C14 C19 0.17(11) . . . . ?
C16 C15 C14 C13 175.08(7) . . . . ?
O3 C13 C14 C15 -135.78(8) . . . . ?
C12 C13 C14 C15 42.21(10) . . . . ?
O3 C13 C14 C19 39.20(10) . . . . ?
C12 C13 C14 C19 -142.81(7) . . . . ?
C14 C15 C16 C17 0.77(11) . . . . ?
C15 C14 C19 C18 -1.32(11) . . . . ?
C13 C14 C19 C18 -176.38(7) . . . . ?
C15 C16 C17 C18 -0.56(12) . . . . ?
C14 C19 C18 C17 1.54(12) . . . . ?
C16 C17 C18 C19 -0.60(12) . . . . ?
