#------------------------------------------------------------------------------
#$Date: 2025-04-05 04:43:15 +0200 (Sat 05 de Apr de 2025) $
#$Revision: 298869 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/97/7249757.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_7249757
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         'C21 H21 N O4'
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39
_chemical_melting_point          112
_chemical_name_common            Indolizine
_chemical_name_systematic
;
ethyl 7-methoxy-2-methyl-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                 97.34(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.539(5)
_cell_length_b                   4.4810(9)
_cell_length_c                   16.013(3)
_cell_measurement_reflns_used    28249
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8
_cell_measurement_theta_min      0.8
_cell_volume                     1746.3(6)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0396
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28249
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.754
_diffrn_reflns_theta_min         0.824
_diffrn_source                   Synchrotron
_exptl_absorpt_coefficient_mu    0.089
_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    1.336
_exptl_crystal_density_meas      1.34
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_transmission_factor_max   0.998
_exptl_transmission_factor_min   0.991
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0429
_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)+(0.0855P)²+0.3195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1259
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4476
_reflns_number_total             5220
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01018c2.cif
_cod_data_source_block           5n
_cod_depositor_comments
'Adding full bibliography for 7249753--7249759.cif.'
_cod_original_cell_volume        1746.4(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249757
_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 0.39819(3) 0.29193(18) 0.64175(4) 0.02627(16) Uani 1 1 d . . . . .
O3 O 0.12419(3) 0.22567(19) 0.56797(4) 0.02808(17) Uani 1 1 d . . . . .
O1 O 0.37650(3) 0.04633(19) 0.75538(4) 0.02905(17) Uani 1 1 d . . . . .
O4 O 0.30730(3) 0.99378(17) 0.42325(4) 0.02807(17) Uani 1 1 d . . . . .
N1 N 0.23145(3) 0.46638(18) 0.58291(4) 0.02013(16) Uani 1 1 d . . . . .
C5 C 0.28818(4) 0.4614(2) 0.59189(5) 0.01964(17) Uani 1 1 d . . . . .
C6 C 0.30539(4) 0.2683(2) 0.66042(5) 0.01957(17) Uani 1 1 d . . . . .
C10 C 0.25791(4) 0.1593(2) 0.69242(5) 0.01906(17) Uani 1 1 d . . . . .
C4 C 0.31619(4) 0.6370(2) 0.53796(5) 0.02205(18) Uani 1 1 d . . . . .
H4 H 0.3559(6) 0.628(3) 0.5421(9) 0.028(3) Uiso 1 1 d . . . . .
C7 C 0.36146(4) 0.1887(2) 0.69193(5) 0.02164(18) Uani 1 1 d . . . . .
C13 C 0.15389(4) 0.2031(2) 0.63640(5) 0.02137(18) Uani 1 1 d . . . . .
C12 C 0.21193(4) 0.2810(2) 0.64399(5) 0.01970(17) Uani 1 1 d . . . . .
C14 C 0.12895(4) 0.0942(2) 0.71046(5) 0.02069(17) Uani 1 1 d . . . . .
C15 C 0.14331(4) 0.2154(2) 0.79060(6) 0.02297(18) Uani 1 1 d . . . . .
H15 H 0.1723(6) 0.370(3) 0.7985(9) 0.032(4) Uiso 1 1 d . . . . .
C20 C 0.08657(4) -0.1145(2) 0.69816(6) 0.02368(19) Uani 1 1 d . . . . .
H19 H 0.0764(6) -0.200(3) 0.6422(9) 0.029(3) Uiso 1 1 d . . . . .
C2 C 0.22808(5) 0.8220(2) 0.47365(6) 0.0255(2) Uani 1 1 d . . . . .
H2 H 0.2072(6) 0.958(3) 0.4324(9) 0.032(4) Uiso 1 1 d . . . . .
C11 C 0.25888(4) -0.0609(2) 0.76284(5) 0.02207(18) Uani 1 1 d . . . . .
H11A H 0.2679(6) 0.038(4) 0.8157(10) 0.034(4) Uiso 1 1 d . . . . .
H11B H 0.2883(6) -0.209(3) 0.7597(9) 0.027(3) Uiso 1 1 d . . . . .
H11C H 0.2242(6) -0.163(3) 0.7631(10) 0.032(4) Uiso 1 1 d . . . . .
C3 C 0.28601(4) 0.8139(2) 0.47890(6) 0.02342(19) Uani 1 1 d . . . . .
C1 C 0.20172(4) 0.6494(2) 0.52528(6) 0.02367(19) Uani 1 1 d . . . . .
H1 H 0.1631(5) 0.650(3) 0.5271(8) 0.020(3) Uiso 1 1 d . . . . .
C18 C 0.05969(4) -0.2038(2) 0.76502(6) 0.0259(2) Uani 1 1 d . . . . .
H18 H 0.0310(6) -0.360(4) 0.7554(10) 0.034(4) Uiso 1 1 d . . . . .
C16 C 0.11510(4) 0.1315(2) 0.85680(6) 0.02369(19) Uani 1 1 d . . . . .
H16 H 0.1242(6) 0.231(3) 0.9108(10) 0.035(4) Uiso 1 1 d . . . . .
C17 C 0.07313(4) -0.0794(2) 0.84519(6) 0.02346(19) Uani 1 1 d . . . . .
C21 C 0.04277(5) -0.1715(3) 0.91718(7) 0.0318(2) Uani 1 1 d . . . . .
H21A H 0.0469(7) -0.019(4) 0.9620(11) 0.049(5) Uiso 1 1 d . . . . .
H21B H 0.0553(8) -0.367(5) 0.9413(12) 0.054(5) Uiso 1 1 d . . . . .
H21C H 0.0029(8) -0.197(4) 0.8968(12) 0.057(5) Uiso 1 1 d . . . . .
C19 C 0.36523(5) 0.9826(3) 0.42213(7) 0.0335(2) Uani 1 1 d . . . . .
H20A H 0.3850(7) 1.039(4) 0.4787(11) 0.042(4) Uiso 1 1 d . . . . .
H20B H 0.3729(7) 1.121(4) 0.3778(11) 0.042(4) Uiso 1 1 d . . . . .
H20C H 0.3775(6) 0.787(4) 0.4096(10) 0.039(4) Uiso 1 1 d . . . . .
C8 C 0.45489(5) 0.2383(4) 0.67311(8) 0.0376(3) Uani 1 1 d . . . . .
H8A H 0.4603(8) 0.023(5) 0.6792(12) 0.055(5) Uiso 1 1 d . . . . .
H8B H 0.4626(8) 0.332(4) 0.7293(12) 0.052(5) Uiso 1 1 d . . . . .
C9 C 0.48945(5) 0.3606(4) 0.61002(9) 0.0464(3) Uani 1 1 d . . . . .
H9A H 0.5274(9) 0.346(5) 0.6322(14) 0.070(6) Uiso 1 1 d . . . . .
H9B H 0.4809(8) 0.574(5) 0.5990(13) 0.063(6) Uiso 1 1 d . . . . .
H9C H 0.4831(9) 0.246(5) 0.5561(14) 0.063(6) 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 114.88(8) . . ?
C3 O4 C19 117.16(9) . . ?
C1 N1 C5 121.45(8) . . ?
C1 N1 C12 128.23(8) . . ?
C5 N1 C12 110.15(7) . . ?
N1 C5 C4 119.38(8) . . ?
N1 C5 C6 106.68(8) . . ?
C4 C5 C6 133.92(9) . . ?
C10 C6 C5 108.20(8) . . ?
C10 C6 C7 125.23(8) . . ?
C5 C6 C7 126.55(9) . . ?
C12 C10 C6 107.92(8) . . ?
C12 C10 C11 127.61(9) . . ?
C6 C10 C11 124.39(8) . . ?
C3 C4 C5 118.74(9) . . ?
C3 C4 H4 121.4(9) . . ?
C5 C4 H4 119.9(8) . . ?
O1 C7 O2 121.17(9) . . ?
O1 C7 C6 126.42(9) . . ?
O2 C7 C6 112.41(8) . . ?
O3 C13 C12 120.81(9) . . ?
O3 C13 C14 118.49(9) . . ?
C12 C13 C14 120.70(8) . . ?
C10 C12 N1 107.04(8) . . ?
C10 C12 C13 131.70(9) . . ?
N1 C12 C13 119.84(8) . . ?
C20 C14 C15 119.14(9) . . ?
C20 C14 C13 118.94(8) . . ?
C15 C14 C13 121.66(9) . . ?
C16 C15 C14 120.25(9) . . ?
C16 C15 H15 120.8(9) . . ?
C14 C15 H15 118.8(9) . . ?
C18 C20 C14 120.30(9) . . ?
C18 C20 H19 120.2(8) . . ?
C14 C20 H19 119.5(8) . . ?
C1 C2 C3 120.24(9) . . ?
C1 C2 H2 120.8(9) . . ?
C3 C2 H2 119.0(9) . . ?
C10 C11 H11A 109.9(10) . . ?
C10 C11 H11B 110.3(8) . . ?
H11A C11 H11B 105.7(12) . . ?
C10 C11 H11C 112.7(9) . . ?
H11A C11 H11C 108.6(13) . . ?
H11B C11 H11C 109.4(13) . . ?
O4 C3 C4 125.18(10) . . ?
O4 C3 C2 114.51(9) . . ?
C4 C3 C2 120.31(9) . . ?
C2 C1 N1 119.80(9) . . ?
C2 C1 H1 124.8(8) . . ?
N1 C1 H1 115.3(8) . . ?
C20 C18 C17 120.92(9) . . ?
C20 C18 H18 118.8(9) . . ?
C17 C18 H18 120.3(9) . . ?
C15 C16 C17 120.90(9) . . ?
C15 C16 H16 118.4(9) . . ?
C17 C16 H16 120.7(9) . . ?
C16 C17 C18 118.44(9) . . ?
C16 C17 C21 120.85(9) . . ?
C18 C17 C21 120.71(10) . . ?
C17 C21 H21A 110.6(11) . . ?
C17 C21 H21B 112.4(11) . . ?
H21A C21 H21B 109.2(15) . . ?
C17 C21 H21C 110.0(11) . . ?
H21A C21 H21C 108.9(15) . . ?
H21B C21 H21C 105.6(16) . . ?
O4 C19 H20A 110.3(9) . . ?
O4 C19 H20B 105.8(10) . . ?
H20A C19 H20B 112.3(14) . . ?
O4 C19 H20C 112.1(10) . . ?
H20A C19 H20C 106.9(14) . . ?
H20B C19 H20C 109.4(14) . . ?
O2 C8 C9 107.95(10) . . ?
O2 C8 H8A 108.2(11) . . ?
C9 C8 H8A 110.2(11) . . ?
O2 C8 H8B 108.1(11) . . ?
C9 C8 H8B 113.4(11) . . ?
H8A C8 H8B 108.8(16) . . ?
C8 C9 H9A 109.4(13) . . ?
C8 C9 H9B 110.3(12) . . ?
H9A C9 H9B 107.8(18) . . ?
C8 C9 H9C 110.7(12) . . ?
H9A C9 H9C 108.8(17) . . ?
H9B C9 H9C 109.6(17) . . ?
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 1.3629(12) . ?
O2 C8 1.4377(14) . ?
O3 C13 1.2402(11) . ?
O1 C7 1.2163(12) . ?
O4 C3 1.3547(12) . ?
O4 C19 1.4249(16) . ?
N1 C1 1.3726(12) . ?
N1 C5 1.3814(12) . ?
N1 C12 1.4127(12) . ?
C5 C4 1.4105(13) . ?
C5 C6 1.4185(12) . ?
C6 C10 1.4182(13) . ?
C6 C7 1.4484(13) . ?
C10 C12 1.3958(13) . ?
C10 C11 1.4963(12) . ?
C4 C3 1.3757(13) . ?
C4 H4 0.970(14) . ?
C13 C12 1.4564(13) . ?
C13 C14 1.4848(13) . ?
C14 C20 1.3938(14) . ?
C14 C15 1.3966(12) . ?
C15 C16 1.3899(13) . ?
C15 H15 0.989(16) . ?
C20 C18 1.3862(14) . ?
C20 H19 0.977(15) . ?
C2 C1 1.3555(14) . ?
C2 C3 1.4137(15) . ?
C2 H2 0.993(15) . ?
C11 H11A 0.957(16) . ?
C11 H11B 0.987(14) . ?
C11 H11C 0.967(15) . ?
C1 H1 0.953(13) . ?
C18 C17 1.3997(14) . ?
C18 H18 0.991(16) . ?
C16 C17 1.3927(15) . ?
C16 H16 0.973(16) . ?
C17 C21 1.5077(14) . ?
C21 H21A 0.986(19) . ?
C21 H21B 0.99(2) . ?
C21 H21C 1.00(2) . ?
C19 H20A 1.004(17) . ?
C19 H20B 0.978(18) . ?
C19 H20C 0.958(17) . ?
C8 C9 1.5029(18) . ?
C8 H8A 0.98(2) . ?
C8 H8B 0.989(19) . ?
C9 H9A 0.96(2) . ?
C9 H9B 0.99(2) . ?
C9 H9C 1.00(2) . ?
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
C1 N1 C5 C4 -3.15(13) . . . . ?
C12 N1 C5 C4 -178.72(8) . . . . ?
C1 N1 C5 C6 175.52(8) . . . . ?
C12 N1 C5 C6 -0.05(10) . . . . ?
N1 C5 C6 C10 -0.26(10) . . . . ?
C4 C5 C6 C10 178.12(9) . . . . ?
N1 C5 C6 C7 178.49(9) . . . . ?
C4 C5 C6 C7 -3.12(17) . . . . ?
C5 C6 C10 C12 0.48(10) . . . . ?
C7 C6 C10 C12 -178.29(8) . . . . ?
C5 C6 C10 C11 177.40(8) . . . . ?
C7 C6 C10 C11 -1.37(14) . . . . ?
N1 C5 C4 C3 1.40(13) . . . . ?
C6 C5 C4 C3 -176.83(9) . . . . ?
C8 O2 C7 O1 -4.38(15) . . . . ?
C8 O2 C7 C6 175.68(9) . . . . ?
C10 C6 C7 O1 -8.94(16) . . . . ?
C5 C6 C7 O1 172.51(9) . . . . ?
C10 C6 C7 O2 170.99(8) . . . . ?
C5 C6 C7 O2 -7.55(14) . . . . ?
C6 C10 C12 N1 -0.50(10) . . . . ?
C11 C10 C12 N1 -177.29(8) . . . . ?
C6 C10 C12 C13 165.42(9) . . . . ?
C11 C10 C12 C13 -11.37(16) . . . . ?
C1 N1 C12 C10 -174.84(9) . . . . ?
C5 N1 C12 C10 0.35(10) . . . . ?
C1 N1 C12 C13 17.25(14) . . . . ?
C5 N1 C12 C13 -167.57(8) . . . . ?
O3 C13 C12 C10 -144.81(10) . . . . ?
C14 C13 C12 C10 35.07(15) . . . . ?
O3 C13 C12 N1 19.63(14) . . . . ?
C14 C13 C12 N1 -160.48(8) . . . . ?
O3 C13 C14 C20 33.08(14) . . . . ?
C12 C13 C14 C20 -146.81(10) . . . . ?
O3 C13 C14 C15 -140.90(10) . . . . ?
C12 C13 C14 C15 39.21(14) . . . . ?
C20 C14 C15 C16 -0.87(15) . . . . ?
C13 C14 C15 C16 173.10(9) . . . . ?
C15 C14 C20 C18 -1.04(15) . . . . ?
C13 C14 C20 C18 -175.17(9) . . . . ?
C19 O4 C3 C4 4.57(14) . . . . ?
C19 O4 C3 C2 -176.47(9) . . . . ?
C5 C4 C3 O4 179.90(8) . . . . ?
C5 C4 C3 C2 1.00(14) . . . . ?
C1 C2 C3 O4 179.21(9) . . . . ?
C1 C2 C3 C4 -1.77(14) . . . . ?
C3 C2 C1 N1 0.08(14) . . . . ?
C5 N1 C1 C2 2.40(14) . . . . ?
C12 N1 C1 C2 177.11(9) . . . . ?
C14 C20 C18 C17 2.24(16) . . . . ?
C14 C15 C16 C17 1.62(15) . . . . ?
C15 C16 C17 C18 -0.44(15) . . . . ?
C15 C16 C17 C21 179.65(10) . . . . ?
C20 C18 C17 C16 -1.48(15) . . . . ?
C20 C18 C17 C21 178.43(10) . . . . ?
C7 O2 C8 C9 179.06(11) . . . . ?
