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#$Date: 2022-08-10 04:42:42 +0300 (Wed, 10 Aug 2022) $
#$Revision: 277184 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244142.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_2244142
loop_
_publ_author_name
'Tojiboev, Akmaljon'
'Elmuradov, Burkhon'
'Kattaev, Nuritdin'
'Abdurazakov, Asqar'
'Nasrullayev, Azizbek'
'Tashkhodjaev, Bakhodir'
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and DFT calculations of
 7-bromo-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
;
_journal_coeditor_code           WM5655
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022007800
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C11 H9 Br N2 O'
_chemical_formula_moiety         'C11 H9 Br N2 O'
_chemical_formula_sum            'C11 H9 Br N2 O'
_chemical_formula_weight         265.11
_chemical_name_systematic
;
7-Bromo-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-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   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 105.583(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5654(3)
_cell_length_b                   11.4972(2)
_cell_length_c                   12.1025(3)
_cell_measurement_reflns_used    5905
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      71.3050
_cell_measurement_theta_min      3.7970
_cell_volume                     1013.99(5)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9036
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.484
_diffrn_reflns_theta_min         5.404
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    5.304
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.556
_refine_ls_extinction_coef       0.0045(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick 2015)
;
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0459P)²+0.6636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                1770
_reflns_number_total             1959
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5655sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2244142
_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   0.199
_shelx_estimated_absorpt_t_max   0.619
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 Br 0.90737(5) 0.85845(3) 0.51410(4) 0.0772(2) Uani d 1 . .
O O 0.6024(3) 0.46212(19) 0.28785(15) 0.0704(6) Uani d 1 . .
C C1 0.5525(4) 0.2291(2) 0.3474(2) 0.0524(6) Uani d 1 . .
H H1A 0.615715 0.217862 0.288281 0.063 Uiso calc 1 . .
H H1B 0.424182 0.245293 0.311148 0.063 Uiso calc 1 . .
C C2 0.5725(5) 0.1238(3) 0.4234(3) 0.0646(8) Uani d 1 . .
H H2A 0.660804 0.070068 0.406688 0.077 Uiso calc 1 . .
H H2B 0.455714 0.084094 0.411100 0.077 Uiso calc 1 . .
C C3 0.6385(5) 0.1665(2) 0.5467(2) 0.0573(7) Uani d 1 . .
H H3A 0.541287 0.160567 0.584874 0.069 Uiso calc 1 . .
H H3B 0.742854 0.121317 0.589288 0.069 Uiso calc 1 . .
C C3A 0.6916(4) 0.2907(2) 0.53807(19) 0.0428(5) Uani d 1 . .
N N4 0.7726(4) 0.35675(17) 0.62262(17) 0.0503(5) Uani d 1 . .
C C4A 0.8027(3) 0.4710(2) 0.59434(19) 0.0424(5) Uani d 1 . .
C C5 0.8937(4) 0.5471(2) 0.6820(2) 0.0569(7) Uani d 1 . .
H H5 0.932797 0.519968 0.757050 0.068 Uiso calc 1 . .
C C6 0.9258(4) 0.6610(2) 0.6588(2) 0.0554(7) Uani d 1 . .
H H6 0.986151 0.710837 0.717397 0.066 Uiso calc 1 . .
C C7 0.8667(4) 0.7005(2) 0.5464(2) 0.0490(6) Uani d 1 . .
C C8 0.7793(4) 0.6286(2) 0.4582(2) 0.0486(6) Uani d 1 . .
H H8 0.742035 0.656476 0.383367 0.058 Uiso calc 1 . .
C C8A 0.7471(3) 0.5135(2) 0.48227(19) 0.0403(5) Uani d 1 . .
C C9 0.6560(3) 0.4355(2) 0.38867(19) 0.0451(5) Uani d 1 . .
N N10 0.6368(3) 0.32406(18) 0.42522(15) 0.0405(4) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
N10 C1 C2 . . 104.5(2) ?
N10 C1 H1A . . 110.8 ?
C2 C1 H1A . . 110.8 ?
N10 C1 H1B . . 110.8 ?
C2 C1 H1B . . 110.8 ?
H1A C1 H1B . . 108.9 ?
C1 C2 C3 . . 107.0(2) ?
C1 C2 H2A . . 110.3 ?
C3 C2 H2A . . 110.3 ?
C1 C2 H2B . . 110.3 ?
C3 C2 H2B . . 110.3 ?
H2A C2 H2B . . 108.6 ?
C3A C3 C2 . . 105.3(2) ?
C3A C3 H3A . . 110.7 ?
C2 C3 H3A . . 110.7 ?
C3A C3 H3B . . 110.7 ?
C2 C3 H3B . . 110.7 ?
H3A C3 H3B . . 108.8 ?
N4 C3A N10 . . 125.3(2) ?
N4 C3A C3 . . 125.9(2) ?
N10 C3A C3 . . 108.8(2) ?
C3A N4 C4A . . 115.8(2) ?
N4 C4A C8A . . 122.9(2) ?
N4 C4A C5 . . 118.8(2) ?
C8A C4A C5 . . 118.3(2) ?
C6 C5 C4A . . 121.1(2) ?
C6 C5 H5 . . 119.4 ?
C4A C5 H5 . . 119.4 ?
C5 C6 C7 . . 118.9(2) ?
C5 C6 H6 . . 120.6 ?
C7 C6 H6 . . 120.6 ?
C8 C7 C6 . . 121.8(2) ?
C8 C7 Br . . 119.1(2) ?
C6 C7 Br . . 119.1(2) ?
C7 C8 C8A . . 119.0(2) ?
C7 C8 H8 . . 120.5 ?
C8A C8 H8 . . 120.5 ?
C8 C8A C4A . . 120.8(2) ?
C8 C8A C9 . . 119.6(2) ?
C4A C8A C9 . . 119.6(2) ?
O C9 N10 . . 121.4(2) ?
O C9 C8A . . 125.6(2) ?
N10 C9 C8A . . 112.97(19) ?
C3A N10 C9 . . 123.4(2) ?
C3A N10 C1 . . 113.1(2) ?
C9 N10 C1 . . 123.41(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
Br C7 . 1.900(3) ?
O C9 . 1.217(3) ?
C1 N10 . 1.471(3) ?
C1 C2 . 1.503(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.522(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C3A . 1.494(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C3A N4 . 1.290(3) ?
C3A N10 . 1.371(3) ?
N4 C4A . 1.392(3) ?
C4A C8A . 1.396(3) ?
C4A C5 . 1.404(3) ?
C5 C6 . 1.375(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.389(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.371(4) ?
C8 C8A . 1.391(3) ?
C8 H8 . 0.9300 ?
C8A C9 . 1.464(3) ?
C9 N10 . 1.376(3) ?
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
N10 C1 C2 C3 . . . . 9.8(4) ?
C1 C2 C3 C3A . . . . -11.4(4) ?
C2 C3 C3A N4 . . . . -172.4(3) ?
C2 C3 C3A N10 . . . . 8.8(3) ?
N10 C3A N4 C4A . . . . 0.9(4) ?
C3 C3A N4 C4A . . . . -177.8(3) ?
C3A N4 C4A C8A . . . . 1.0(4) ?
C3A N4 C4A C5 . . . . -178.7(3) ?
N4 C4A C5 C6 . . . . -179.6(3) ?
C8A C4A C5 C6 . . . . 0.7(4) ?
C4A C5 C6 C7 . . . . 0.0(5) ?
C5 C6 C7 C8 . . . . -0.7(4) ?
C5 C6 C7 Br . . . . 179.0(2) ?
C6 C7 C8 C8A . . . . 0.8(4) ?
Br C7 C8 C8A . . . . -179.02(19) ?
C7 C8 C8A C4A . . . . -0.1(4) ?
C7 C8 C8A C9 . . . . -179.2(2) ?
N4 C4A C8A C8 . . . . 179.6(2) ?
C5 C4A C8A C8 . . . . -0.7(4) ?
N4 C4A C8A C9 . . . . -1.2(4) ?
C5 C4A C8A C9 . . . . 178.5(2) ?
C8 C8A C9 O . . . . -0.4(4) ?
C4A C8A C9 O . . . . -179.6(3) ?
C8 C8A C9 N10 . . . . 178.8(2) ?
C4A C8A C9 N10 . . . . -0.3(3) ?
N4 C3A N10 C9 . . . . -2.6(4) ?
C3 C3A N10 C9 . . . . 176.2(2) ?
N4 C3A N10 C1 . . . . 178.4(3) ?
C3 C3A N10 C1 . . . . -2.7(3) ?
O C9 N10 C3A . . . . -178.6(3) ?
C8A C9 N10 C3A . . . . 2.1(3) ?
O C9 N10 C1 . . . . 0.3(4) ?
C8A C9 N10 C1 . . . . -179.0(2) ?
C2 C1 N10 C3A . . . . -4.5(3) ?
C2 C1 N10 C9 . . . . 176.5(2) ?

_cod_database_fobs_code 2244142
