#------------------------------------------------------------------------------
#$Date: 2024-08-31 05:05:05 +0300 (Sat, 31 Aug 2024) $
#$Revision: 294312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/32/2023243.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_2023243
loop_
_publ_author_name
'Pronina, Anastasia A.'
'Kutasevich, Alexandra G.'
'Grigoriev, Mikhail S.'
'Hasanov, Khudayar I.'
'Sadikhova, Nurlana D.'
'Javadzade, Tahir A.'
'Akkurt, Mehmet'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 1-[6-bromo-2-(3-bromophenyl)-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one
;
_journal_coeditor_code           NX2012
_journal_issue                   9
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              967
_journal_page_last               972
_journal_paper_doi               10.1107/S2056989024008144
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C19 H18 Br2 N2 O'
_chemical_formula_moiety         'C19 H18 Br2 N2 O'
_chemical_formula_sum            'C19 H18 Br2 N2 O'
_chemical_formula_weight         450.17
_chemical_name_systematic
1-[6-Bromo-2-(3-bromophenyl)-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one
_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
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 104.364(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8691(8)
_cell_length_b                   9.4578(7)
_cell_length_c                   17.7217(14)
_cell_measurement_reflns_used    5029
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.90
_cell_volume                     1764.8(2)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         4.162
_exptl_absorpt_coefficient_mu    4.601
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_description       bulk
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.472
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0290
_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)+(0.0176P)²+1.5651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0528
_refine_ls_wR_factor_ref         0.0574
_reflns_number_gt                3231
_reflns_number_total             4041
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nx2012.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2023243
_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   0.288
_shelx_estimated_absorpt_t_max   0.381
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
C C2 0.3972(2) 0.7031(2) 0.42197(14) 0.0095(5) Uani d 1 . .
H H2 0.417106 0.695439 0.480026 0.011 Uiso calc 1 . .
C C3 0.5184(2) 0.7407(2) 0.39791(14) 0.0103(5) Uani d 1 . .
H H3A 0.551079 0.833284 0.420260 0.012 Uiso calc 1 . .
H H3B 0.500982 0.746994 0.340468 0.012 Uiso calc 1 . .
C C4 0.6161(2) 0.6251(2) 0.42821(14) 0.0090(5) Uani d 1 . .
H H4A 0.623691 0.617392 0.485461 0.011 Uiso calc 1 . .
C C4A 0.5649(2) 0.4840(2) 0.39280(14) 0.0103(5) Uani d 1 . .
C C5 0.6438(2) 0.3756(2) 0.37979(14) 0.0116(5) Uani d 1 . .
H H5A 0.732382 0.391768 0.387756 0.014 Uiso calc 1 . .
C C6 0.5933(2) 0.2444(2) 0.35526(14) 0.0141(5) Uani d 1 . .
C C7 0.4649(2) 0.2184(2) 0.34323(14) 0.0153(5) Uani d 1 . .
H H7A 0.431556 0.127113 0.327685 0.018 Uiso calc 1 . .
C C8 0.3852(2) 0.3264(2) 0.35403(14) 0.0141(5) Uani d 1 . .
H H8A 0.296550 0.309470 0.344583 0.017 Uiso calc 1 . .
C C8A 0.4337(2) 0.4609(2) 0.37876(14) 0.0099(5) Uani d 1 . .
C C12 0.8464(2) 0.6433(2) 0.47857(15) 0.0108(5) Uani d 1 . .
C C13 0.9605(2) 0.6920(2) 0.45130(16) 0.0164(6) Uani d 1 . .
H H13A 1.014249 0.610573 0.444761 0.020 Uiso calc 1 . .
H H13B 1.012448 0.759132 0.488933 0.020 Uiso calc 1 . .
C C14 0.9045(2) 0.7642(2) 0.37321(16) 0.0183(6) Uani d 1 . .
H H14A 0.954217 0.740510 0.335083 0.022 Uiso calc 1 . .
H H14B 0.903707 0.868151 0.379516 0.022 Uiso calc 1 . .
C C15 0.7689(2) 0.7064(2) 0.34649(15) 0.0140(5) Uani d 1 . .
H H15A 0.708860 0.781053 0.321194 0.017 Uiso calc 1 . .
H H15B 0.764491 0.626563 0.309794 0.017 Uiso calc 1 . .
C C21 0.2979(2) 0.8177(2) 0.39562(14) 0.0098(5) Uani d 1 . .
C C22 0.2170(2) 0.8162(2) 0.32186(14) 0.0108(5) Uani d 1 . .
H H22 0.219100 0.739884 0.287317 0.013 Uiso calc 1 . .
C C23 0.1327(2) 0.9274(2) 0.29887(14) 0.0113(5) Uani d 1 . .
C C24 0.1280(2) 1.0400(2) 0.34733(16) 0.0176(6) Uani d 1 . .
H H24 0.070147 1.115604 0.330570 0.021 Uiso calc 1 . .
C C25 0.2095(3) 1.0404(3) 0.42109(17) 0.0207(6) Uani d 1 . .
H H25 0.207518 1.117252 0.455296 0.025 Uiso calc 1 . .
C C26 0.2935(2) 0.9304(2) 0.44550(15) 0.0157(5) Uani d 1 . .
H H26 0.348384 0.931566 0.496389 0.019 Uiso calc 1 . .
N N1 0.35049(19) 0.5666(2) 0.38807(12) 0.0121(4) Uani d 1 . .
H H1 0.283(3) 0.538(3) 0.3999(15) 0.014 Uiso d 1 . .
N N11 0.74188(18) 0.65967(19) 0.41920(12) 0.0105(4) Uani d 1 . .
O O1 0.84580(15) 0.59639(17) 0.54316(10) 0.0153(4) Uani d 1 . .
Br Br1 0.70318(3) 0.09579(2) 0.34029(2) 0.02171(8) Uani d 1 . .
Br Br2 0.01897(2) 0.91972(2) 0.19816(2) 0.01641(7) Uani 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'
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'
Br Br -0.2901 2.4595 '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
N1 C2 C21 . . 110.84(19) ?
N1 C2 C3 . . 109.13(19) ?
C21 C2 C3 . . 110.18(18) ?
N1 C2 H2 . . 108.9 ?
C21 C2 H2 . . 108.9 ?
C3 C2 H2 . . 108.9 ?
C2 C3 C4 . . 107.97(18) ?
C2 C3 H3A . . 110.1 ?
C4 C3 H3A . . 110.1 ?
C2 C3 H3B . . 110.1 ?
C4 C3 H3B . . 110.1 ?
H3A C3 H3B . . 108.4 ?
N11 C4 C4A . . 114.22(19) ?
N11 C4 C3 . . 113.07(18) ?
C4A C4 C3 . . 109.42(19) ?
N11 C4 H4A . . 106.5 ?
C4A C4 H4A . . 106.5 ?
C3 C4 H4A . . 106.5 ?
C5 C4A C8A . . 119.8(2) ?
C5 C4A C4 . . 122.5(2) ?
C8A C4A C4 . . 117.5(2) ?
C6 C5 C4A . . 120.0(2) ?
C6 C5 H5A . . 120.0 ?
C4A C5 H5A . . 120.0 ?
C7 C6 C5 . . 121.1(2) ?
C7 C6 Br1 . . 119.47(17) ?
C5 C6 Br1 . . 119.45(19) ?
C6 C7 C8 . . 119.4(2) ?
C6 C7 H7A . . 120.3 ?
C8 C7 H7A . . 120.3 ?
C7 C8 C8A . . 120.9(2) ?
C7 C8 H8A . . 119.6 ?
C8A C8 H8A . . 119.6 ?
N1 C8A C4A . . 122.1(2) ?
N1 C8A C8 . . 119.0(2) ?
C4A C8A C8 . . 118.9(2) ?
O1 C12 N11 . . 124.7(2) ?
O1 C12 C13 . . 127.0(2) ?
N11 C12 C13 . . 108.3(2) ?
C12 C13 C14 . . 104.5(2) ?
C12 C13 H13A . . 110.8 ?
C14 C13 H13A . . 110.8 ?
C12 C13 H13B . . 110.8 ?
C14 C13 H13B . . 110.8 ?
H13A C13 H13B . . 108.9 ?
C13 C14 C15 . . 104.92(19) ?
C13 C14 H14A . . 110.8 ?
C15 C14 H14A . . 110.8 ?
C13 C14 H14B . . 110.8 ?
C15 C14 H14B . . 110.8 ?
H14A C14 H14B . . 108.8 ?
N11 C15 C14 . . 102.9(2) ?
N11 C15 H15A . . 111.2 ?
C14 C15 H15A . . 111.2 ?
N11 C15 H15B . . 111.2 ?
C14 C15 H15B . . 111.2 ?
H15A C15 H15B . . 109.1 ?
C22 C21 C26 . . 119.6(2) ?
C22 C21 C2 . . 121.3(2) ?
C26 C21 C2 . . 119.0(2) ?
C21 C22 C23 . . 119.2(2) ?
C21 C22 H22 . . 120.4 ?
C23 C22 H22 . . 120.4 ?
C24 C23 C22 . . 121.8(2) ?
C24 C23 Br2 . . 119.92(18) ?
C22 C23 Br2 . . 118.28(18) ?
C23 C24 C25 . . 118.5(2) ?
C23 C24 H24 . . 120.7 ?
C25 C24 H24 . . 120.7 ?
C26 C25 C24 . . 120.8(2) ?
C26 C25 H25 . . 119.6 ?
C24 C25 H25 . . 119.6 ?
C25 C26 C21 . . 120.1(2) ?
C25 C26 H26 . . 119.9 ?
C21 C26 H26 . . 119.9 ?
C8A N1 C2 . . 121.08(19) ?
C8A N1 H1 . . 115.4(17) ?
C2 N1 H1 . . 114.1(17) ?
C12 N11 C4 . . 121.4(2) ?
C12 N11 C15 . . 114.0(2) ?
C4 N11 C15 . . 124.49(19) ?
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
C2 N1 . 1.460(3) ?
C2 C21 . 1.519(3) ?
C2 C3 . 1.524(3) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.526(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 N11 . 1.453(3) ?
C4 C4A . 1.520(3) ?
C4 H4A . 1.0000 ?
C4A C5 . 1.392(3) ?
C4A C8A . 1.402(3) ?
C5 C6 . 1.383(3) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.380(4) ?
C6 Br1 . 1.905(2) ?
C7 C8 . 1.383(3) ?
C7 H7A . 0.9500 ?
C8 C8A . 1.404(3) ?
C8 H8A . 0.9500 ?
C8A N1 . 1.386(3) ?
C12 O1 . 1.229(3) ?
C12 N11 . 1.352(3) ?
C12 C13 . 1.511(3) ?
C13 C14 . 1.528(4) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.532(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 N11 . 1.459(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C21 C22 . 1.383(3) ?
C21 C26 . 1.393(3) ?
C22 C23 . 1.389(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.376(3) ?
C23 Br2 . 1.903(2) ?
C24 C25 . 1.385(4) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.381(3) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
N1 H1 . 0.86(3) ?
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
C13 H13A O1 3_766 0.99 2.46 3.431(3) 168.5 yes
C13 H13A Br2 2_645 0.99 3.06 3.740(3) 127.2 yes
C14 H14A Br2 2_645 0.99 3.12 3.664(3) 116.2 yes
C14 H14B Br1 1_565 0.99 3.02 3.786(2) 135.1 yes
C15 H15A Br1 1_565 0.99 3.00 3.748(2) 133.4 yes
C15 H15B Br2 2_645 0.99 3.09 3.768(2) 126.8 yes
C22 H22 Br1 2_655 0.95 2.94 3.820(2) 154.9 yes
C24 H24 Br2 2 0.95 3.04 3.932(2) 157.6 yes
N1 H1 O1 3_666 0.86(3) 2.30(3) 3.115(3) 159(2) yes
C2 H2 Cg3 3_666 1.00 2.66 3.655(3) 173 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
N1 C2 C3 C4 . . . . -60.0(2) ?
C21 C2 C3 C4 . . . . 178.05(19) ?
C2 C3 C4 N11 . . . . -171.22(19) ?
C2 C3 C4 C4A . . . . 60.2(2) ?
N11 C4 C4A C5 . . . . 22.9(3) ?
C3 C4 C4A C5 . . . . 150.8(2) ?
N11 C4 C4A C8A . . . . -162.0(2) ?
C3 C4 C4A C8A . . . . -34.1(3) ?
C8A C4A C5 C6 . . . . -1.9(4) ?
C4 C4A C5 C6 . . . . 173.1(2) ?
C4A C5 C6 C7 . . . . 0.0(4) ?
C4A C5 C6 Br1 . . . . -178.40(18) ?
C5 C6 C7 C8 . . . . 1.6(4) ?
Br1 C6 C7 C8 . . . . -179.91(18) ?
C6 C7 C8 C8A . . . . -1.5(4) ?
C5 C4A C8A N1 . . . . -177.6(2) ?
C4 C4A C8A N1 . . . . 7.2(3) ?
C5 C4A C8A C8 . . . . 2.0(3) ?
C4 C4A C8A C8 . . . . -173.2(2) ?
C7 C8 C8A N1 . . . . 179.3(2) ?
C7 C8 C8A C4A . . . . -0.3(4) ?
O1 C12 C13 C14 . . . . -169.8(2) ?
N11 C12 C13 C14 . . . . 10.3(2) ?
C12 C13 C14 C15 . . . . -20.3(2) ?
C13 C14 C15 N11 . . . . 22.5(2) ?
N1 C2 C21 C22 . . . . -34.5(3) ?
C3 C2 C21 C22 . . . . 86.4(3) ?
N1 C2 C21 C26 . . . . 149.1(2) ?
C3 C2 C21 C26 . . . . -90.0(3) ?
C26 C21 C22 C23 . . . . 0.0(3) ?
C2 C21 C22 C23 . . . . -176.4(2) ?
C21 C22 C23 C24 . . . . 0.5(4) ?
C21 C22 C23 Br2 . . . . -178.16(17) ?
C22 C23 C24 C25 . . . . -0.5(4) ?
Br2 C23 C24 C25 . . . . 178.1(2) ?
C23 C24 C25 C26 . . . . 0.0(4) ?
C24 C25 C26 C21 . . . . 0.5(4) ?
C22 C21 C26 C25 . . . . -0.5(4) ?
C2 C21 C26 C25 . . . . 176.0(2) ?
C4A C8A N1 C2 . . . . -7.4(4) ?
C8 C8A N1 C2 . . . . 173.0(2) ?
C21 C2 N1 C8A . . . . 155.7(2) ?
C3 C2 N1 C8A . . . . 34.2(3) ?
O1 C12 N11 C4 . . . . 1.7(3) ?
C13 C12 N11 C4 . . . . -178.46(19) ?
O1 C12 N11 C15 . . . . -175.2(2) ?
C13 C12 N11 C15 . . . . 4.7(3) ?
C4A C4 N11 C12 . . . . -101.7(2) ?
C3 C4 N11 C12 . . . . 132.3(2) ?
C4A C4 N11 C15 . . . . 74.8(3) ?
C3 C4 N11 C15 . . . . -51.2(3) ?
C14 C15 N11 C12 . . . . -17.5(2) ?
C14 C15 N11 C4 . . . . 165.80(19) ?
