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#$Date: 2024-11-09 04:46:40 +0200 (Sat, 09 Nov 2024) $
#$Revision: 295853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/33/2023313.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023313
loop_
_publ_author_name
'Mahadevaiah, Harish Kumar'
'Shivanna, Harishkumar'
'Hanumaiah, Anil Kumar'
'Hirehalli Chikkegowda, Devarajegowda'
'Bandrehalli Siddagangaiah, Palakshamurthy'
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis, DFT and molecular docking
 studies of ethyl 5-amino-2-bromoisonicotinate
;
_journal_coeditor_code           OI2013
_journal_issue                   12
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024010594
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C8 H9 Br N2 O2'
_chemical_formula_moiety         'C8 H9 Br N2 O2'
_chemical_formula_sum            'C8 H9 Br N2 O2'
_chemical_formula_weight         245.08
_chemical_name_common
;
Ethyl 5-amino-2-bromoisonicotinate
;
_chemical_name_systematic
;
Ethyl 5-amino-2-bromopyridine-4-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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 92.468(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.1538(9)
_cell_length_b                   8.9978(16)
_cell_length_c                   25.487(5)
_cell_measurement_reflns_used    2367
_cell_measurement_temperature    567(2)
_cell_measurement_theta_max      29.0
_cell_measurement_theta_min      2.5
_cell_volume                     951.7(3)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      567(2)
_diffrn_detector_area_resol_mean 0.97
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and Ω scans'
_diffrn_radiation_monochromator  Graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            21643
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.259
_diffrn_reflns_theta_min         2.772
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.288
_exptl_absorpt_correction_T_max  0.401
_exptl_absorpt_correction_T_min  0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_description       Prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.447
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0.12
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0316
_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)+(0.0216P)²+0.6676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0689
_reflns_number_gt                1910
_reflns_number_total             2353
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oi2013.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2023313
_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   0.341
_shelx_estimated_absorpt_t_max   0.466
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.50981(7) 0.23668(3) 0.33291(2) 0.06255(12) Uani d 1 . .
O O1 0.6756(4) 0.71953(17) 0.44789(6) 0.0519(4) Uani d 1 . .
O O2 0.4245(5) 0.91607(19) 0.41176(7) 0.0678(5) Uani d 1 . .
N N2 0.0811(7) 0.8705(3) 0.31867(10) 0.0679(7) Uani d 1 . .
C C1 0.3910(5) 0.6820(2) 0.36780(8) 0.0389(4) Uani d 1 . .
C C2 0.1949(6) 0.7303(2) 0.32486(8) 0.0451(5) Uani d 1 . .
C C3 0.1106(6) 0.6220(3) 0.28677(9) 0.0511(6) Uani d 1 . .
H H3 -0.019460 0.651860 0.258076 0.061 Uiso calc 1 . .
N N1 0.2016(5) 0.4817(2) 0.28864(7) 0.0480(5) Uani d 1 . .
C C4 0.3867(5) 0.4403(2) 0.32981(8) 0.0419(5) Uani d 1 . .
C C5 0.4870(5) 0.5336(2) 0.36960(8) 0.0414(5) Uani d 1 . .
H H5 0.617469 0.498569 0.397470 0.050 Uiso calc 1 . .
C C6 0.4947(6) 0.7863(3) 0.41030(8) 0.0455(5) Uani d 1 . .
C C7 0.7917(7) 0.8112(3) 0.49174(9) 0.0558(6) Uani d 1 . .
H H7A 0.612483 0.860208 0.507725 0.067 Uiso calc 1 . .
H H7B 0.938171 0.886598 0.479721 0.067 Uiso calc 1 . .
C C8 0.9601(8) 0.7121(4) 0.53018(11) 0.0737(8) Uani d 1 . .
H H8A 1.039906 0.769478 0.559719 0.111 Uiso calc 1 . .
H H8B 0.812758 0.638136 0.541835 0.111 Uiso calc 1 . .
H H8C 1.137029 0.664411 0.513954 0.111 Uiso calc 1 . .
H H2A -0.018(6) 0.889(3) 0.2911(12) 0.064(8) Uiso d 1 . .
H H2B 0.141(7) 0.934(3) 0.3432(12) 0.067(9) Uiso d 1 . .
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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 O1 C7 . . 117.00(18) ?
C2 N2 H2A . . 117(2) ?
C2 N2 H2B . . 115.9(19) ?
H2A N2 H2B . . 127(3) ?
C5 C1 C2 . . 118.54(19) ?
C5 C1 C6 . . 120.56(19) ?
C2 C1 C6 . . 120.9(2) ?
N2 C2 C1 . . 124.5(2) ?
N2 C2 C3 . . 119.3(2) ?
C1 C2 C3 . . 116.2(2) ?
N1 C3 C2 . . 125.1(2) ?
N1 C3 H3 . . 117.4 ?
C2 C3 H3 . . 117.4 ?
C3 N1 C4 . . 116.92(19) ?
N1 C4 C5 . . 124.2(2) ?
N1 C4 Br1 . . 116.65(15) ?
C5 C4 Br1 . . 119.19(16) ?
C4 C5 C1 . . 119.1(2) ?
C4 C5 H5 . . 120.5 ?
C1 C5 H5 . . 120.5 ?
O2 C6 O1 1 . 123.0(2) ?
O2 C6 O1 . . 123.0(2) ?
O2 C6 C1 1 . 125.0(2) ?
O2 C6 C1 . . 125.0(2) ?
O1 C6 C1 . . 112.08(19) ?
O1 C7 C8 . . 107.4(2) ?
O1 C7 H7A . . 110.2 ?
C8 C7 H7A . . 110.2 ?
O1 C7 H7B . . 110.2 ?
C8 C7 H7B . . 110.2 ?
H7A C7 H7B . . 108.5 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C4 . 1.903(2) ?
O1 C6 . 1.335(3) ?
O1 C7 . 1.454(2) ?
O2 C6 . 1.204(3) ?
N2 C2 . 1.354(3) ?
N2 H2A . 0.82(3) ?
N2 H2B . 0.87(3) ?
C1 C5 . 1.393(3) ?
C1 C2 . 1.405(3) ?
C1 C6 . 1.483(3) ?
C2 C3 . 1.409(3) ?
C3 N1 . 1.318(3) ?
C3 H3 . 0.9300 ?
N1 C4 . 1.327(3) ?
C4 C5 . 1.368(3) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.478(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2B O2 1 0.87(3) 2.07(3) 2.746(3) 133(2) yes
C5 H5 O1 1 0.93 2.3700 2.694(3) 99.88(3) y
N2 H2A N1 2 0.82(3) 2.30(3) 3.096(3) 166(3) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 C1 C2 N2 . . . . 179.0(2) ?
C6 C1 C2 N2 . . . . -1.2(4) ?
C5 C1 C2 C3 . . . . 0.2(3) ?
C6 C1 C2 C3 . . . . -180.0(2) ?
N2 C2 C3 N1 . . . . -179.0(3) ?
C1 C2 C3 N1 . . . . -0.1(4) ?
C2 C3 N1 C4 . . . . 0.1(4) ?
C3 N1 C4 C5 . . . . -0.2(3) ?
C3 N1 C4 Br1 . . . . 178.77(18) ?
N1 C4 C5 C1 . . . . 0.3(4) ?
Br1 C4 C5 C1 . . . . -178.67(16) ?
C2 C1 C5 C4 . . . . -0.2(3) ?
C6 C1 C5 C4 . . . . 179.9(2) ?
C7 O1 C6 O2 . . . 1 -0.6(4) ?
C7 O1 C6 O2 . . . . -0.6(4) ?
C7 O1 C6 C1 . . . . 180.0(2) ?
C5 C1 C6 O2 . . . 1 179.6(2) ?
C2 C1 C6 O2 . . . 1 -0.2(4) ?
C5 C1 C6 O2 . . . . 179.6(2) ?
C2 C1 C6 O2 . . . . -0.2(4) ?
C5 C1 C6 O1 . . . . -1.0(3) ?
C2 C1 C6 O1 . . . . 179.1(2) ?
C6 O1 C7 C8 . . . . 175.2(2) ?
