#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/56/2215602.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_2215602
loop_
_publ_author_name
'Butcher, Ray J.'
'Jasinski, Jerry P.'
'Narayana, B.'
'Sunil, K.'
'Yathirajan, H. S.'
_publ_contact_author_address
;
Department of Chemistry
Keene State College
229 Main Street
Keene, New Hampshire 03435-2001
USA
;
_publ_contact_author_email       jjasinski@keene.edu
_publ_contact_author_fax         '603 358-2987'
_publ_contact_author_name        'Jasinski, Jerry P.'
_publ_contact_author_phone       '603 358-2563'
_publ_section_title
2-(4-Chlorophenyl)-3-{[(1E)-(4-chlorophenyl)methylene]amino}-2,3-dihydroquinazolin-4(1H)-one
_journal_coeditor_code           NC2054
_journal_date_accepted           2007-09-05
_journal_date_recd_electronic    2007-08-09
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4025
_journal_page_last               o4026
_journal_paper_category          QO
_journal_paper_doi               10.1107/S1600536807043632
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C21 H15 Cl2 N3 O'
_chemical_formula_moiety         'C21 H15 Cl2 N3 O'
_chemical_formula_sum            'C21 H15 Cl2 N3 O'
_chemical_formula_weight         396.26
_chemical_name_systematic
;
2-(4-Chlorophenyl)-3-{[(1E)-(4-chlorophenyl)methylene]amino}-2,3-
dihydroquinazolin-4(1H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.010(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8774(2)
_cell_length_b                   13.7315(3)
_cell_length_c                   20.4667(8)
_cell_measurement_reflns_used    4254
_cell_measurement_temperature    203
_cell_measurement_theta_max      32.4924
_cell_measurement_theta_min      4.7208
_cell_volume                     1918.37(10)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      203
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.1264
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16112
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.57
_diffrn_reflns_theta_min         4.73
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.629
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         6303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.629
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0550
_reflns_number_gt                2674
_reflns_number_total             6303
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2054.cif
_cod_data_source_block           I
_cod_original_cell_volume        1918.36(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2215602
_cod_database_fobs_code          2215602
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl Cl1 -0.10011(6) 0.67297(3) 1.01418(2) 0.06572(16) Uani d . 1 . .
Cl Cl2A 0.2071(12) 0.0619(3) 0.9802(4) 0.0822(5) Uani d P 0.143(3) A 1
Cl Cl2B 0.1030(2) 0.06077(5) 0.94734(8) 0.0822(5) Uani d P 0.857(3) A 2
O O1 0.65192(12) 0.52725(6) 0.74083(5) 0.0381(3) Uani d . 1 . .
N N1 0.74123(16) 0.23816(9) 0.75887(6) 0.0327(3) Uani d . 1 . .
H H1A 0.7714(16) 0.1785(9) 0.7664(6) 0.034(4) Uiso d . 1 . .
N N2 0.59892(14) 0.38310(7) 0.79096(6) 0.0289(3) Uani d . 1 . .
N N3 0.51282(17) 0.43070(8) 0.84227(6) 0.0365(3) Uani d . 1 . .
C C1 0.68930(18) 0.43957(10) 0.74828(7) 0.0302(4) Uani d . 1 . .
C C2 0.83198(18) 0.38806(9) 0.71214(7) 0.0277(3) Uani d . 1 . .
C C3 0.94084(19) 0.43931(10) 0.67071(7) 0.0392(4) Uani d . 1 . .
H H3A 0.9251 0.5071 0.6663 0.047 Uiso calc R 1 . .
C C4 1.0717(2) 0.39151(11) 0.63603(8) 0.0461(5) Uani d . 1 . .
H H4A 1.1477 0.4266 0.6089 0.055 Uiso calc R 1 . .
C C5 1.09004(19) 0.29123(11) 0.64157(8) 0.0438(4) Uani d . 1 . .
H H5A 1.1773 0.2583 0.6173 0.053 Uiso calc R 1 . .
C C6 0.98294(18) 0.23944(10) 0.68187(7) 0.0366(4) Uani d . 1 . .
H H6A 0.9965 0.1714 0.6849 0.044 Uiso calc R 1 . .
C C7 0.85406(18) 0.28752(9) 0.71830(7) 0.0290(3) Uani d . 1 . .
C C8 0.68991(19) 0.28985(9) 0.81588(8) 0.0348(4) Uani d . 1 . .
H H8A 0.8092 0.3031 0.8468 0.042 Uiso calc R 1 . .
C C9 0.5468(2) 0.23071(9) 0.84980(8) 0.0311(4) Uani d . 1 A .
C C10 0.5939(2) 0.19858(10) 0.91276(9) 0.0454(4) Uani d . 1 . .
H H10A 0.7185 0.2122 0.9351 0.055 Uiso calc R 1 . .
C C11 0.4605(3) 0.14606(11) 0.94427(9) 0.0576(5) Uani d . 1 A .
H H11A 0.4933 0.1247 0.9879 0.069 Uiso calc R 1 . .
C C12 0.2817(3) 0.12593(11) 0.91110(11) 0.0555(5) Uani d . 1 . .
C C13 0.2316(2) 0.15577(11) 0.84789(11) 0.0562(5) Uani d . 1 A .
H H13A 0.1078 0.1407 0.8254 0.067 Uiso calc R 1 . .
C C14 0.3658(2) 0.20870(10) 0.81721(8) 0.0454(4) Uani d . 1 . .
H H14A 0.3326 0.2298 0.7736 0.055 Uiso calc R 1 A .
C C15 0.3577(2) 0.47659(10) 0.82277(8) 0.0366(4) Uani d . 1 . .
H H15A 0.3095 0.4768 0.7778 0.044 Uiso calc R 1 . .
C C16 0.2520(2) 0.52966(9) 0.86972(8) 0.0307(4) Uani d . 1 . .
C C17 0.3345(2) 0.54820(10) 0.93330(8) 0.0425(4) Uani d . 1 . .
H H17A 0.4655 0.5304 0.9463 0.051 Uiso calc R 1 . .
C C18 0.2287(2) 0.59239(10) 0.97826(8) 0.0448(4) Uani d . 1 . .
H H18A 0.2860 0.6043 1.0216 0.054 Uiso calc R 1 . .
C C19 0.0381(2) 0.61862(10) 0.95834(9) 0.0394(4) Uani d . 1 . .
C C20 -0.0444(2) 0.60432(11) 0.89521(9) 0.0514(5) Uani d . 1 . .
H H20A -0.1738 0.6245 0.8819 0.062 Uiso calc R 1 . .
C C21 0.0633(2) 0.55979(11) 0.85062(8) 0.0464(4) Uani d . 1 . .
H H21A 0.0067 0.5501 0.8069 0.056 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
C7 N1 C8 117.04(12)
C7 N1 H1A 115.9(9)
C8 N1 H1A 113.8(9)
C1 N2 N3 118.10(10)
C1 N2 C8 120.02(10)
N3 N2 C8 109.70(11)
C15 N3 N2 114.02(13)
O1 C1 N2 121.67(12)
O1 C1 C2 122.99(13)
N2 C1 C2 115.33(12)
C3 C2 C7 119.76(12)
C3 C2 C1 120.20(12)
C7 C2 C1 120.03(13)
C4 C3 C2 120.50(13)
C4 C3 H3A 119.7
C2 C3 H3A 119.7
C3 C4 C5 119.29(14)
C3 C4 H4A 120.4
C5 C4 H4A 120.4
C6 C5 C4 120.99(14)
C6 C5 H5A 119.5
C4 C5 H5A 119.5
C5 C6 C7 120.02(13)
C5 C6 H6A 120.0
C7 C6 H6A 120.0
N1 C7 C6 122.02(12)
N1 C7 C2 118.53(12)
C6 C7 C2 119.41(13)
N1 C8 N2 106.24(12)
N1 C8 C9 110.14(11)
N2 C8 C9 110.50(10)
N1 C8 H8A 110.0
N2 C8 H8A 110.0
C9 C8 H8A 110.0
C10 C9 C14 119.02(14)
C10 C9 C8 121.07(14)
C14 C9 C8 119.92(14)
C9 C10 C11 120.92(16)
C9 C10 H10A 119.5
C11 C10 H10A 119.5
C12 C11 C10 118.91(16)
C12 C11 H11A 120.5
C10 C11 H11A 120.5
C11 C12 C13 121.48(16)
C11 C12 Cl2B 122.01(18)
C13 C12 Cl2B 116.50(18)
C11 C12 Cl2A 92.0(3)
C13 C12 Cl2A 146.5(4)
Cl2B C12 Cl2A 30.1(3)
C12 C13 C14 118.95(17)
C12 C13 H13A 120.5
C14 C13 H13A 120.5
C9 C14 C13 120.71(16)
C9 C14 H14A 119.6
C13 C14 H14A 119.6
N3 C15 C16 120.56(14)
N3 C15 H15A 119.7
C16 C15 H15A 119.7
C21 C16 C17 118.64(14)
C21 C16 C15 119.34(15)
C17 C16 C15 121.99(13)
C16 C17 C18 121.34(14)
C16 C17 H17A 119.3
C18 C17 H17A 119.3
C19 C18 C17 118.64(15)
C19 C18 H18A 120.7
C17 C18 H18A 120.7
C20 C19 C18 121.11(15)
C20 C19 Cl1 119.17(13)
C18 C19 Cl1 119.71(14)
C19 C20 C21 119.64(15)
C19 C20 H20A 120.2
C21 C20 H20A 120.2
C16 C21 C20 120.54(16)
C16 C21 H21A 119.7
C20 C21 H21A 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C19 1.7410(14)
Cl2A C12 1.793(6)
Cl2B C12 1.7556(17)
O1 C1 1.2367(14)
N1 C7 1.3815(16)
N1 C8 1.4457(17)
N1 H1A 0.854(12)
N2 C1 1.3722(16)
N2 N3 1.4258(14)
N2 C8 1.4878(15)
N3 C15 1.2610(15)
C1 C2 1.4789(17)
C2 C3 1.3892(17)
C2 C7 1.3929(17)
C3 C4 1.3786(17)
C3 H3A 0.9400
C4 C5 1.3862(18)
C4 H4A 0.9400
C5 C6 1.3699(17)
C5 H5A 0.9400
C6 C7 1.3924(16)
C6 H6A 0.9400
C8 C9 1.5090(17)
C8 H8A 0.9900
C9 C10 1.3630(19)
C9 C14 1.3722(18)
C10 C11 1.386(2)
C10 H10A 0.9400
C11 C12 1.359(2)
C11 H11A 0.9400
C12 C13 1.361(2)
C13 C14 1.384(2)
C13 H13A 0.9400
C14 H14A 0.9400
C15 C16 1.4677(18)
C15 H15A 0.9400
C16 C21 1.3723(17)
C16 C17 1.3786(18)
C17 C18 1.3814(18)
C17 H17A 0.9400
C18 C19 1.3724(18)
C18 H18A 0.9400
C19 C20 1.361(2)
C20 C21 1.3861(19)
C20 H20A 0.9400
C21 H21A 0.9400
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
N1 H1A O1 2_646 0.854(12) 2.153(13) 2.9877(15) 165.7(12)
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
C1 N2 N3 C15 72.35(15)
C8 N2 N3 C15 -145.13(11)
N3 N2 C1 O1 -20.85(19)
C8 N2 C1 O1 -159.42(13)
N3 N2 C1 C2 159.47(11)
C8 N2 C1 C2 20.89(18)
O1 C1 C2 C3 4.3(2)
N2 C1 C2 C3 -176.04(12)
O1 C1 C2 C7 -174.11(13)
N2 C1 C2 C7 5.58(19)
C7 C2 C3 C4 -0.5(2)
C1 C2 C3 C4 -178.91(13)
C2 C3 C4 C5 1.7(2)
C3 C4 C5 C6 -1.2(2)
C4 C5 C6 C7 -0.3(2)
C8 N1 C7 C6 150.60(13)
C8 N1 C7 C2 -31.76(19)
C5 C6 C7 N1 179.12(13)
C5 C6 C7 C2 1.5(2)
C3 C2 C7 N1 -178.77(13)
C1 C2 C7 N1 -0.4(2)
C3 C2 C7 C6 -1.1(2)
C1 C2 C7 C6 177.32(13)
C7 N1 C8 N2 53.23(15)
C7 N1 C8 C9 172.93(12)
C1 N2 C8 N1 -48.54(15)
N3 N2 C8 N1 169.77(10)
C1 N2 C8 C9 -168.00(13)
N3 N2 C8 C9 50.31(15)
N1 C8 C9 C10 117.64(15)
N2 C8 C9 C10 -125.28(14)
N1 C8 C9 C14 -62.48(16)
N2 C8 C9 C14 54.59(17)
C14 C9 C10 C11 -1.3(2)
C8 C9 C10 C11 178.60(13)
C9 C10 C11 C12 0.7(2)
C10 C11 C12 C13 0.3(2)
C10 C11 C12 Cl2B -179.45(11)
C10 C11 C12 Cl2A 179.9(2)
C11 C12 C13 C14 -0.7(2)
Cl2B C12 C13 C14 179.05(11)
Cl2A C12 C13 C14 -180.0(3)
C10 C9 C14 C13 0.8(2)
C8 C9 C14 C13 -179.04(12)
C12 C13 C14 C9 0.1(2)
N2 N3 C15 C16 -179.84(11)
N3 C15 C16 C21 -165.09(13)
N3 C15 C16 C17 13.2(2)
C21 C16 C17 C18 2.7(2)
C15 C16 C17 C18 -175.57(13)
C16 C17 C18 C19 -0.5(2)
C17 C18 C19 C20 -1.9(2)
C17 C18 C19 Cl1 179.14(11)
C18 C19 C20 C21 2.0(2)
Cl1 C19 C20 C21 -179.03(12)
C17 C16 C21 C20 -2.6(2)
C15 C16 C21 C20 175.72(14)
C19 C20 C21 C16 0.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 96878437
