#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/66/2226662.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_2226662
loop_
_publ_author_name
'Elmuradov, Burkhon Zh.'
'Okmanov, Rasul Ya.'
'Abdurazakov, Asqar Sh.'
'Tashkhodjaev, Bakhodir'
'Shakhidoyatov, Khusnutdin M.'
_publ_section_title
;
 (E)-3-[4-(Dimethylamino)benzylidene]-2,3-dihydro-1H,9H-pyrrolo[2,1-b]quinazolin-9-one
;
_journal_coeditor_code           SI2264
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1592
_journal_paper_doi               10.1107/S1600536810020878
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H19 N3 O'
_chemical_formula_moiety         'C20 H19 N3 O'
_chemical_formula_sum            'C20 H19 N3 O'
_chemical_formula_weight         317.38
_chemical_melting_point          514(2)
_chemical_name_systematic
;
(E)-3-[4-(Dimethylamino)benzylidene]-2,3-dihydro-
1H,9H-pyrrolo[2,1-b]quinazolin-9-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.05(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8030(18)
_cell_length_b                   16.415(3)
_cell_length_c                   11.463(2)
_cell_measurement_reflns_used    12
_cell_measurement_temperature    300.0(10)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      10
_cell_volume                     1599.6(6)
_computing_cell_refinement       'STADI4 (Stoe & Cie, 1997)'
_computing_data_collection       'STADI4 (Stoe & Cie, 1997)'
_computing_data_reduction        'X-RED (Stoe & Cie, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300.0(10)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Stoe Stadi-4 4-circle-diffractometer D092'
_diffrn_measurement_device_type  'Stoe Stadi-4 four-circle'
_diffrn_measurement_method
; Scan width (omega) = 1.32 - 1.56, scan ratio 2theta:omega = 0.00
  I(Net) and sigma(I) calculated according to Blessing (1987)
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2446
_diffrn_reflns_theta_full        60.00
_diffrn_reflns_theta_max         60.00
_diffrn_reflns_theta_min         4.82
_diffrn_standards_decay_%        10.0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  0.9062
_exptl_absorpt_correction_T_min  0.8543
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
(X-RED; Stoe & Cie, 1997).
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizmatic
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.179
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0446P)²+1.0639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1415
_reflns_number_gt                1728
_reflns_number_total             2342
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            si2264.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226662
_cod_database_fobs_code          2226662
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.1964(3) 0.57316(13) 0.07780(19) 0.0553(7) Uani d . 1 . .
C C1 0.0365(4) 0.48250(18) 0.2373(3) 0.0496(9) Uani d . 1 . .
H H1A 0.0818 0.4880 0.1691 0.060 Uiso calc R 1 . .
H H1B -0.0432 0.4402 0.2197 0.060 Uiso calc R 1 . .
C C2 0.1634(4) 0.46318(18) 0.3530(3) 0.0435(8) Uani d . 1 . .
H H2A 0.1435 0.4107 0.3851 0.052 Uiso calc R 1 . .
H H2B 0.2663 0.4617 0.3370 0.052 Uiso calc R 1 . .
C C3 0.1562(3) 0.52982(17) 0.4410(3) 0.0373(7) Uani d . 1 . .
C C3A 0.0343(3) 0.58741(17) 0.3798(2) 0.0355(7) Uani d . 1 . .
N N4 -0.0078(3) 0.65349(14) 0.4246(2) 0.0391(6) Uani d . 1 . .
C C4A -0.1278(3) 0.69758(17) 0.3470(3) 0.0378(7) Uani d . 1 . .
C C5 -0.1799(4) 0.76888(18) 0.3914(3) 0.0459(8) Uani d . 1 . .
H H5A -0.1330 0.7856 0.4700 0.055 Uiso calc R 1 . .
C C6 -0.2995(4) 0.8144(2) 0.3201(3) 0.0495(8) Uani d . 1 . .
H H6A -0.3327 0.8618 0.3503 0.059 Uiso calc R 1 . .
C C7 -0.3707(4) 0.78958(19) 0.2026(3) 0.0476(8) Uani d . 1 . .
H H7A -0.4525 0.8201 0.1549 0.057 Uiso calc R 1 . .
C C8 -0.3213(3) 0.72058(19) 0.1568(3) 0.0452(8) Uani d . 1 . .
H H8A -0.3690 0.7047 0.0780 0.054 Uiso calc R 1 . .
C C8A -0.1995(3) 0.67373(17) 0.2279(3) 0.0379(7) Uani d . 1 . .
C C9 -0.1474(3) 0.59996(18) 0.1804(3) 0.0413(7) Uani d . 1 . .
N N10 -0.0298(3) 0.55973(14) 0.2639(2) 0.0384(6) Uani d . 1 . .
N N1' 0.7209(3) 0.34893(18) 0.8577(2) 0.0585(8) Uani d . 1 . .
C C1' 0.3643(3) 0.49063(17) 0.6292(2) 0.0375(7) Uani d . 1 . .
C C2' 0.4284(4) 0.42189(18) 0.5885(3) 0.0445(8) Uani d . 1 . .
H H2'A 0.3902 0.4064 0.5081 0.053 Uiso calc R 1 . .
C C3' 0.5455(4) 0.37605(19) 0.6621(3) 0.0451(8) Uani d . 1 . .
H H3'A 0.5847 0.3310 0.6303 0.054 Uiso calc R 1 . .
C C4' 0.6065(3) 0.39601(18) 0.7836(3) 0.0426(8) Uani d . 1 . .
C C5' 0.5453(4) 0.46547(19) 0.8262(3) 0.0462(8) Uani d . 1 . .
H H5'A 0.5839 0.4812 0.9064 0.055 Uiso calc R 1 . .
C C6' 0.4282(3) 0.51068(18) 0.7500(3) 0.0423(8) Uani d . 1 . .
H H6'A 0.3904 0.5566 0.7808 0.051 Uiso calc R 1 . .
C C7' 0.2395(3) 0.54038(17) 0.5554(3) 0.0383(7) Uani d . 1 . .
H H7'A 0.2135 0.5864 0.5934 0.046 Uiso calc R 1 . .
C C8' 0.7668(5) 0.3632(3) 0.9855(3) 0.0906(15) Uani d . 1 . .
H H8'A 0.6753 0.3623 1.0164 0.136 Uiso calc R 1 . .
H H8'B 0.8171 0.4154 1.0015 0.136 Uiso calc R 1 . .
H H8'C 0.8386 0.3214 1.0243 0.136 Uiso calc R 1 . .
C C9' 0.7788(4) 0.2766(2) 0.8122(3) 0.0617(10) Uani d . 1 . .
H H9'A 0.8256 0.2912 0.7482 0.093 Uiso calc R 1 . .
H H9'B 0.6932 0.2397 0.7818 0.093 Uiso calc R 1 . .
H H9'C 0.8562 0.2509 0.8762 0.093 Uiso calc R 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'
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 . . 103.9(2) ?
N10 C1 H1A . . 111.0 ?
C2 C1 H1A . . 111.0 ?
N10 C1 H1B . . 111.0 ?
C2 C1 H1B . . 111.0 ?
H1A C1 H1B . . 109.0 ?
C3 C2 C1 . . 106.4(2) ?
C3 C2 H2A . . 110.4 ?
C1 C2 H2A . . 110.4 ?
C3 C2 H2B . . 110.4 ?
C1 C2 H2B . . 110.4 ?
H2A C2 H2B . . 108.6 ?
C7' C3 C3A . . 122.2(3) ?
C7' C3 C2 . . 130.2(3) ?
C3A C3 C2 . . 107.6(2) ?
N4 C3A N10 . . 124.8(3) ?
N4 C3A C3 . . 126.9(3) ?
N10 C3A C3 . . 108.3(2) ?
C3A N4 C4A . . 115.4(2) ?
N4 C4A C5 . . 117.9(3) ?
N4 C4A C8A . . 123.4(3) ?
C5 C4A C8A . . 118.7(3) ?
C6 C5 C4A . . 120.7(3) ?
C6 C5 H5A . . 119.6 ?
C4A C5 H5A . . 119.6 ?
C5 C6 C7 . . 120.0(3) ?
C5 C6 H6A . . 120.0 ?
C7 C6 H6A . . 120.0 ?
C8 C7 C6 . . 120.4(3) ?
C8 C7 H7A . . 119.8 ?
C6 C7 H7A . . 119.8 ?
C7 C8 C8A . . 120.3(3) ?
C7 C8 H8A . . 119.8 ?
C8A C8 H8A . . 119.8 ?
C8 C8A C4A . . 119.8(3) ?
C8 C8A C9 . . 120.7(3) ?
C4A C8A C9 . . 119.5(3) ?
O1 C9 N10 . . 120.5(3) ?
O1 C9 C8A . . 126.4(3) ?
N10 C9 C8A . . 113.1(3) ?
C3A N10 C9 . . 123.8(2) ?
C3A N10 C1 . . 113.7(2) ?
C9 N10 C1 . . 122.5(2) ?
C4' N1' C8' . . 120.5(3) ?
C4' N1' C9' . . 120.7(3) ?
C8' N1' C9' . . 118.2(3) ?
C6' C1' C2' . . 115.5(3) ?
C6' C1' C7' . . 119.7(3) ?
C2' C1' C7' . . 124.8(3) ?
C3' C2' C1' . . 122.8(3) ?
C3' C2' H2'A . . 118.6 ?
C1' C2' H2'A . . 118.6 ?
C2' C3' C4' . . 121.1(3) ?
C2' C3' H3'A . . 119.4 ?
C4' C3' H3'A . . 119.4 ?
N1' C4' C3' . . 121.0(3) ?
N1' C4' C5' . . 121.8(3) ?
C3' C4' C5' . . 117.1(3) ?
C6' C5' C4' . . 120.5(3) ?
C6' C5' H5'A . . 119.8 ?
C4' C5' H5'A . . 119.8 ?
C5' C6' C1' . . 123.0(3) ?
C5' C6' H6'A . . 118.5 ?
C1' C6' H6'A . . 118.5 ?
C3 C7' C1' . . 129.6(3) ?
C3 C7' H7'A . . 115.2 ?
C1' C7' H7'A . . 115.2 ?
N1' C8' H8'A . . 109.5 ?
N1' C8' H8'B . . 109.5 ?
H8'A C8' H8'B . . 109.5 ?
N1' C8' H8'C . . 109.5 ?
H8'A C8' H8'C . . 109.5 ?
H8'B C8' H8'C . . 109.5 ?
N1' C9' H9'A . . 109.5 ?
N1' C9' H9'B . . 109.5 ?
H9'A C9' H9'B . . 109.5 ?
N1' C9' H9'C . . 109.5 ?
H9'A C9' H9'C . . 109.5 ?
H9'B C9' H9'C . . 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
O1 C9 . 1.225(3) ?
C1 N10 . 1.461(4) ?
C1 C2 . 1.529(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.500(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C7' . 1.338(4) ?
C3 C3A . 1.465(4) ?
C3A N4 . 1.295(3) ?
C3A N10 . 1.378(3) ?
N4 C4A . 1.394(4) ?
C4A C5 . 1.400(4) ?
C4A C8A . 1.403(4) ?
C5 C6 . 1.374(4) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.390(4) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.366(4) ?
C7 H7A . 0.9300 ?
C8 C8A . 1.397(4) ?
C8 H8A . 0.9300 ?
C8A C9 . 1.450(4) ?
C9 N10 . 1.382(4) ?
N1' C4' . 1.375(4) ?
N1' C8' . 1.434(4) ?
N1' C9' . 1.442(4) ?
C1' C6' . 1.392(4) ?
C1' C2' . 1.395(4) ?
C1' C7' . 1.452(4) ?
C2' C3' . 1.374(4) ?
C2' H2'A . 0.9300 ?
C3' C4' . 1.395(4) ?
C3' H3'A . 0.9300 ?
C4' C5' . 1.402(4) ?
C5' C6' . 1.381(4) ?
C5' H5'A . 0.9300 ?
C6' H6'A . 0.9300 ?
C7' H7'A . 0.9300 ?
C8' H8'A . 0.9600 ?
C8' H8'B . 0.9600 ?
C8' H8'C . 0.9600 ?
C9' H9'A . 0.9600 ?
C9' H9'B . 0.9600 ?
C9' H9'C . 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745226
2 PubChem 12603619
