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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/7/24/97/7249753.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_7249753
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         'C19 H17 N O4'
_chemical_formula_sum            'C19 H17 N O4'
_chemical_formula_weight         323.33
_chemical_melting_point          132
_chemical_name_common            Indolizine
_chemical_name_systematic
;
ethyl 3-benzoyl-7-methoxyindolizine-1-carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                86.29(3)
_cell_angle_beta                 82.15(3)
_cell_angle_gamma                83.83(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2400(12)
_cell_length_b                   10.620(2)
_cell_length_c                   12.070(2)
_cell_measurement_reflns_used    27764
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8
_cell_measurement_theta_min      1.7
_cell_volume                     786.8(3)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0199
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27764
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.760
_diffrn_reflns_theta_min         1.680
_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    1.365
_exptl_crystal_density_meas      1.36
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_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         0.793
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.136(11)
_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   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0423
_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)+(0.0686P)²+0.2745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4548
_reflns_number_total             4649
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01018c2.cif
_cod_data_source_block           5a
_cod_depositor_comments
'Adding full bibliography for 7249753--7249759.cif.'
_cod_database_code               7249753
_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, -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_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 1.05066(10) 0.60721(6) 0.60619(5) 0.01607(14) Uani 1 1 d . . . . .
O3 O 0.07472(11) 0.70858(7) 0.86792(6) 0.02184(16) Uani 1 1 d . . . . .
O1 O 1.09930(11) 0.41365(6) 0.69308(6) 0.02001(15) Uani 1 1 d . . . . .
O4 O 0.57504(11) 0.15544(7) 0.96761(6) 0.02165(16) Uani 1 1 d . . . . .
N1 N 0.45033(12) 0.52188(7) 0.84565(6) 0.01420(15) Uani 1 1 d . . . . .
C7 C 0.98657(13) 0.51276(8) 0.67973(7) 0.01456(16) Uani 1 1 d . . . . .
C6 C 0.76870(13) 0.54370(8) 0.73723(7) 0.01449(16) Uani 1 1 d . . . . .
C10 C 0.63429(13) 0.65702(8) 0.72828(7) 0.01488(16) Uani 1 1 d . . . . .
H10 H 0.673(2) 0.7311(13) 0.6807(11) 0.020(3) Uiso 1 1 d . . . . .
C13 C 0.25528(14) 0.86401(8) 0.75448(7) 0.01609(17) Uani 1 1 d . . . . .
C5 C 0.65202(13) 0.45916(8) 0.81166(7) 0.01419(16) Uani 1 1 d . . . . .
C11 C 0.43749(13) 0.64556(8) 0.79591(7) 0.01453(16) Uani 1 1 d . . . . .
C4 C 0.70535(14) 0.33360(8) 0.85191(7) 0.01574(16) Uani 1 1 d . . . . .
H4 H 0.848(2) 0.2918(14) 0.8281(12) 0.024(3) Uiso 1 1 d . . . . .
C1 C 0.29609(14) 0.46325(9) 0.91845(7) 0.01653(17) Uani 1 1 d . . . . .
H1 H 0.167(2) 0.5117(14) 0.9370(12) 0.023(3) Uiso 1 1 d . . . . .
C8 C 1.26066(13) 0.57810(8) 0.54052(7) 0.01570(16) Uani 1 1 d . . . . .
H8A H 1.254(2) 0.5015(13) 0.4991(11) 0.018(3) Uiso 1 1 d . . . . .
H8B H 1.368(2) 0.5592(13) 0.5916(11) 0.019(3) Uiso 1 1 d . . . . .
C12 C 0.24656(13) 0.73495(8) 0.81186(7) 0.01572(16) Uani 1 1 d . . . . .
C18 C 0.08475(14) 0.90949(9) 0.69438(8) 0.01990(18) Uani 1 1 d . . . . .
H18 H -0.025(2) 0.8536(15) 0.6882(13) 0.028(4) Uiso 1 1 d . . . . .
C3 C 0.55014(14) 0.27535(8) 0.92273(7) 0.01762(17) Uani 1 1 d . . . . .
C14 C 0.41903(15) 0.94126(9) 0.76335(8) 0.01997(18) Uani 1 1 d . . . . .
H14 H 0.533(2) 0.9100(14) 0.8066(12) 0.026(3) Uiso 1 1 d . . . . .
C17 C 0.07896(16) 1.02986(9) 0.64224(9) 0.0236(2) Uani 1 1 d . . . . .
H17 H -0.041(3) 1.0622(16) 0.6000(13) 0.032(4) Uiso 1 1 d . . . . .
C9 C 1.30533(15) 0.69109(9) 0.46167(8) 0.02042(18) Uani 1 1 d . . . . .
H9A H 1.445(3) 0.6723(16) 0.4151(13) 0.032(4) Uiso 1 1 d . . . . .
H9B H 1.308(3) 0.7685(16) 0.5045(14) 0.035(4) Uiso 1 1 d . . . . .
H9C H 1.191(3) 0.7093(16) 0.4112(13) 0.032(4) Uiso 1 1 d . . . . .
C15 C 0.40961(17) 1.06317(9) 0.71304(9) 0.0245(2) Uani 1 1 d . . . . .
H15 H 0.526(3) 1.1166(16) 0.7209(14) 0.034(4) Uiso 1 1 d . . . . .
C19 C 0.78220(16) 0.08468(9) 0.94162(9) 0.02265(19) Uani 1 1 d . . . . .
H19A H 0.820(3) 0.0757(15) 0.8616(13) 0.030(4) Uiso 1 1 d . . . . .
H19B H 0.767(3) 0.0019(16) 0.9790(14) 0.036(4) Uiso 1 1 d . . . . .
H19C H 0.893(2) 0.1262(15) 0.9693(13) 0.030(4) Uiso 1 1 d . . . . .
C2 C 0.34422(15) 0.34239(9) 0.95710(8) 0.02170(19) Uani 1 1 d . . . . .
H2 H 0.233(3) 0.3011(15) 1.0072(13) 0.032(4) Uiso 1 1 d . . . . .
C16 C 0.24072(17) 1.10755(9) 0.65190(9) 0.0248(2) Uani 1 1 d . . . . .
H16 H 0.234(3) 1.1931(17) 0.6168(14) 0.037(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 114.40(7) . . ?
C3 O4 C19 117.29(8) . . ?
C5 N1 C1 121.15(8) . . ?
C5 N1 C11 109.64(7) . . ?
C1 N1 C11 129.21(8) . . ?
O1 C7 O2 122.87(8) . . ?
O1 C7 C6 125.20(8) . . ?
O2 C7 C6 111.92(8) . . ?
C10 C6 C5 107.54(8) . . ?
C10 C6 C7 127.87(8) . . ?
C5 C6 C7 124.57(8) . . ?
C11 C10 C6 109.11(8) . . ?
C11 C10 H10 126.1(8) . . ?
C6 C10 H10 124.8(8) . . ?
C18 C13 C14 119.57(8) . . ?
C18 C13 C12 117.40(8) . . ?
C14 C13 C12 122.96(8) . . ?
N1 C5 C4 120.28(8) . . ?
N1 C5 C6 107.13(8) . . ?
C4 C5 C6 132.59(8) . . ?
C10 C11 N1 106.56(8) . . ?
C10 C11 C12 129.64(8) . . ?
N1 C11 C12 123.72(8) . . ?
C3 C4 C5 118.21(8) . . ?
C3 C4 H4 122.8(9) . . ?
C5 C4 H4 119.0(9) . . ?
C2 C1 N1 119.27(8) . . ?
C2 C1 H1 125.2(9) . . ?
N1 C1 H1 115.5(9) . . ?
O2 C8 C9 107.72(8) . . ?
O2 C8 H8A 108.1(8) . . ?
C9 C8 H8A 111.4(8) . . ?
O2 C8 H8B 108.2(8) . . ?
C9 C8 H8B 112.6(8) . . ?
H8A C8 H8B 108.6(11) . . ?
O3 C12 C11 122.93(8) . . ?
O3 C12 C13 118.78(8) . . ?
C11 C12 C13 118.26(8) . . ?
C17 C18 C13 120.41(9) . . ?
C17 C18 H18 121.5(9) . . ?
C13 C18 H18 118.0(9) . . ?
O4 C3 C4 125.42(9) . . ?
O4 C3 C2 114.20(8) . . ?
C4 C3 C2 120.36(8) . . ?
C15 C14 C13 119.75(9) . . ?
C15 C14 H14 121.3(9) . . ?
C13 C14 H14 118.9(9) . . ?
C18 C17 C16 120.14(9) . . ?
C18 C17 H17 120.5(10) . . ?
C16 C17 H17 119.3(10) . . ?
C8 C9 H9A 108.9(10) . . ?
C8 C9 H9B 110.7(10) . . ?
H9A C9 H9B 110.2(14) . . ?
C8 C9 H9C 111.0(9) . . ?
H9A C9 H9C 108.1(13) . . ?
H9B C9 H9C 108.0(13) . . ?
C16 C15 C14 120.48(9) . . ?
C16 C15 H15 121.0(10) . . ?
C14 C15 H15 118.5(10) . . ?
O4 C19 H19A 111.7(9) . . ?
O4 C19 H19B 105.2(10) . . ?
H19A C19 H19B 109.6(13) . . ?
O4 C19 H19C 109.9(9) . . ?
H19A C19 H19C 109.2(13) . . ?
H19B C19 H19C 111.2(13) . . ?
C1 C2 C3 120.69(9) . . ?
C1 C2 H2 118.8(10) . . ?
C3 C2 H2 120.5(10) . . ?
C17 C16 C15 119.62(9) . . ?
C17 C16 H16 119.8(10) . . ?
C15 C16 H16 120.6(10) . . ?
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 1.3521(11) . ?
O2 C8 1.4499(11) . ?
O3 C12 1.2362(11) . ?
O1 C7 1.2160(11) . ?
O4 C3 1.3529(11) . ?
O4 C19 1.4301(12) . ?
N1 C5 1.3821(11) . ?
N1 C1 1.3831(11) . ?
N1 C11 1.4072(11) . ?
C7 C6 1.4539(12) . ?
C6 C10 1.3980(12) . ?
C6 C5 1.4145(12) . ?
C10 C11 1.3910(12) . ?
C10 H10 0.976(14) . ?
C13 C18 1.3953(13) . ?
C13 C14 1.3964(13) . ?
C13 C12 1.4980(12) . ?
C5 C4 1.4106(12) . ?
C11 C12 1.4408(12) . ?
C4 C3 1.3732(12) . ?
C4 H4 0.967(15) . ?
C1 C2 1.3540(13) . ?
C1 H1 0.917(15) . ?
C8 C9 1.5083(13) . ?
C8 H8A 0.989(13) . ?
C8 H8B 0.969(14) . ?
C18 C17 1.3868(13) . ?
C18 H18 0.967(15) . ?
C3 C2 1.4235(13) . ?
C14 C15 1.3928(13) . ?
C14 H14 0.957(15) . ?
C17 C16 1.3916(15) . ?
C17 H17 0.984(16) . ?
C9 H9A 0.981(16) . ?
C9 H9B 1.002(17) . ?
C9 H9C 0.996(16) . ?
C15 C16 1.3920(15) . ?
C15 H15 0.987(17) . ?
C19 H19A 0.971(16) . ?
C19 H19B 0.970(17) . ?
C19 H19C 0.968(16) . ?
C2 H2 0.976(16) . ?
C16 H16 0.977(18) . ?
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 2.89(12) . . . . ?
C8 O2 C7 C6 -175.83(7) . . . . ?
O1 C7 C6 C10 177.72(9) . . . . ?
O2 C7 C6 C10 -3.59(12) . . . . ?
O1 C7 C6 C5 -4.28(14) . . . . ?
O2 C7 C6 C5 174.41(7) . . . . ?
C5 C6 C10 C11 0.46(10) . . . . ?
C7 C6 C10 C11 178.73(8) . . . . ?
C1 N1 C5 C4 -0.68(12) . . . . ?
C11 N1 C5 C4 179.03(7) . . . . ?
C1 N1 C5 C6 179.25(7) . . . . ?
C11 N1 C5 C6 -1.04(9) . . . . ?
C10 C6 C5 N1 0.36(9) . . . . ?
C7 C6 C5 N1 -177.98(7) . . . . ?
C10 C6 C5 C4 -179.73(9) . . . . ?
C7 C6 C5 C4 1.93(15) . . . . ?
C6 C10 C11 N1 -1.08(9) . . . . ?
C6 C10 C11 C12 -177.94(8) . . . . ?
C5 N1 C11 C10 1.32(9) . . . . ?
C1 N1 C11 C10 -179.00(8) . . . . ?
C5 N1 C11 C12 178.41(8) . . . . ?
C1 N1 C11 C12 -1.91(14) . . . . ?
N1 C5 C4 C3 1.69(12) . . . . ?
C6 C5 C4 C3 -178.22(9) . . . . ?
C5 N1 C1 C2 0.14(13) . . . . ?
C11 N1 C1 C2 -179.51(8) . . . . ?
C7 O2 C8 C9 178.78(7) . . . . ?
C10 C11 C12 O3 173.82(9) . . . . ?
N1 C11 C12 O3 -2.56(14) . . . . ?
C10 C11 C12 C13 -4.00(14) . . . . ?
N1 C11 C12 C13 179.62(7) . . . . ?
C18 C13 C12 O3 -46.99(12) . . . . ?
C14 C13 C12 O3 129.85(10) . . . . ?
C18 C13 C12 C11 130.92(9) . . . . ?
C14 C13 C12 C11 -52.23(12) . . . . ?
C14 C13 C18 C17 0.96(14) . . . . ?
C12 C13 C18 C17 177.91(8) . . . . ?
C19 O4 C3 C4 1.84(14) . . . . ?
C19 O4 C3 C2 -176.68(8) . . . . ?
C5 C4 C3 O4 179.40(8) . . . . ?
C5 C4 C3 C2 -2.16(13) . . . . ?
C18 C13 C14 C15 0.56(14) . . . . ?
C12 C13 C14 C15 -176.21(9) . . . . ?
C13 C18 C17 C16 -1.63(15) . . . . ?
C13 C14 C15 C16 -1.43(15) . . . . ?
N1 C1 C2 C3 -0.62(14) . . . . ?
O4 C3 C2 C1 -179.72(9) . . . . ?
C4 C3 C2 C1 1.68(14) . . . . ?
C18 C17 C16 C15 0.77(16) . . . . ?
C14 C15 C16 C17 0.76(16) . . . . ?
