#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:41:36 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299000 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/37/1573729.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1573729
loop_
_publ_author_name
'Korica, Milenko'
'Komar, Mario'
'Molnar, Maja'
'Nemec, Vinko'
'Cinčić, Dominik'
'Balić, Tomislav'
_publ_section_title
;
 Structural and thermal properties of 3-substituted quinazolinone Schiff
 base conjugates
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3067
_journal_page_last               3077
_journal_paper_doi               10.1039/D4NJ04028G
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C16 H12 Cl N3 O'
_chemical_formula_sum            'C16 H12 Cl N3 O'
_chemical_formula_weight         297.74
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-01-17 deposited with the CCDC.	2025-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                71.525(3)
_cell_angle_beta                 76.046(3)
_cell_angle_gamma                81.964(3)
_cell_formula_units_Z            4
_cell_length_a                   7.9879(3)
_cell_length_b                   13.1032(4)
_cell_length_c                   14.7678(6)
_cell_measurement_reflns_used    8912
_cell_measurement_temperature    294.99(12)
_cell_measurement_theta_max      37.9100
_cell_measurement_theta_min      2.7430
_cell_volume                     1419.40(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_molecular_graphics    'WINGX v2020.1 (Farrugia, 2022)'
_computing_publication_material  'WINGX v2020.1 (Farrugia, 2022)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294.99(12)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22130
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.634
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0477
_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)+(0.0892P)²+0.0834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1415
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3806
_reflns_number_total             5005
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj04028g2.cif
_cod_data_source_block           SB4
_cod_depositor_comments
'Adding full bibliography for 1573726--1573730.cif.'
_cod_original_cell_volume        1419.40(10)
_cod_database_code               1573729
_shelx_shelxl_version_number     2019/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.05396(10) 0.89462(5) 0.65933(4) 0.0775(2) Uani 1 1 d . . . . .
Cl2 Cl 0.65741(12) 0.86286(7) 0.17355(5) 0.1106(3) Uani 1 1 d . . . . .
O1 O 0.3352(2) 0.65193(11) 0.83077(9) 0.0594(4) Uani 1 1 d . . . . .
N1 N 0.1534(2) 0.63208(11) 0.98040(10) 0.0443(4) Uani 1 1 d . . . . .
O2 O 0.2800(2) 0.63969(11) 0.31005(10) 0.0701(5) Uani 1 1 d . . . . .
N4 N 0.3006(2) 0.61784(11) 0.46698(11) 0.0465(4) Uani 1 1 d . . . . .
N3 N 0.0931(2) 0.74207(12) 0.95816(11) 0.0498(4) Uani 1 1 d . . . . .
N2 N 0.1506(2) 0.47078(13) 1.11018(11) 0.0501(4) Uani 1 1 d . . . . .
N6 N 0.3227(2) 0.72881(12) 0.44811(11) 0.0525(4) Uani 1 1 d . . . . .
N5 N 0.2418(2) 0.45648(13) 0.59369(11) 0.0536(4) Uani 1 1 d . . . . .
C3 C 0.3359(3) 0.48041(15) 0.94996(13) 0.0448(4) Uani 1 1 d . . . . .
C1 C 0.1001(3) 0.57114(15) 1.07749(13) 0.0456(5) Uani 1 1 d . . . . .
C19 C 0.2252(2) 0.46961(15) 0.42729(14) 0.0464(5) Uani 1 1 d . . . . .
C8 C 0.2685(3) 0.42317(15) 1.04702(13) 0.0460(5) Uani 1 1 d . . . . .
C24 C 0.2126(3) 0.41178(15) 0.52601(14) 0.0479(5) Uani 1 1 d . . . . .
C2 C 0.2804(3) 0.59357(15) 0.91281(13) 0.0446(4) Uani 1 1 d . . . . .
C18 C 0.2698(3) 0.58142(15) 0.39373(13) 0.0494(5) Uani 1 1 d . . . . .
C11 C -0.0204(3) 0.89464(15) 0.84952(13) 0.0476(5) Uani 1 1 d . . . . .
C17 C 0.2811(3) 0.55551(16) 0.56439(13) 0.0492(5) Uani 1 1 d . . . . .
C10 C 0.0496(3) 0.78138(15) 0.87656(14) 0.0485(5) Uani 1 1 d . . . . .
H10 H 0.061571 0.739781 0.834444 0.058 Uiso 1 1 calc R U . . .
C12 C -0.0264(3) 0.95298(16) 0.75353(14) 0.0506(5) Uani 1 1 d . . . . .
C27 C 0.4712(3) 0.88160(15) 0.34790(14) 0.0505(5) Uani 1 1 d . . . . .
C26 C 0.4423(3) 0.76675(15) 0.37594(14) 0.0508(5) Uani 1 1 d . . . . .
H26 H 0.510802 0.722377 0.341227 0.061 Uiso 1 1 calc R U . . .
C4 C 0.4551(3) 0.42940(17) 0.88968(15) 0.0558(5) Uani 1 1 d . . . . .
H4 H 0.500997 0.468191 0.825755 0.067 Uiso 1 1 calc R U . . .
C13 C -0.0914(3) 1.05959(17) 0.72963(16) 0.0606(6) Uani 1 1 d . . . . .
H13 H -0.092821 1.097704 0.664876 0.073 Uiso 1 1 calc R U . . .
C7 C 0.3240(3) 0.31481(16) 1.08087(16) 0.0583(6) Uani 1 1 d . . . . .
H7 H 0.282566 0.275827 1.145384 0.070 Uiso 1 1 calc R U . . .
C20 C 0.1957(3) 0.42106(18) 0.36164(16) 0.0601(6) Uani 1 1 d . . . . .
H20 H 0.204126 0.460231 0.296236 0.072 Uiso 1 1 calc R U . . .
C28 C 0.5670(3) 0.93400(18) 0.25693(16) 0.0615(6) Uani 1 1 d . . . . .
C23 C 0.1667(3) 0.30459(17) 0.55701(17) 0.0636(6) Uani 1 1 d . . . . .
H23 H 0.155414 0.264692 0.622389 0.076 Uiso 1 1 calc R U . . .
C9 C -0.0222(3) 0.62648(18) 1.14362(15) 0.0620(6) Uani 1 1 d . . . . .
H9A H -0.051740 0.576324 1.207557 0.093 Uiso 1 1 calc R U . . .
H9B H -0.125163 0.653047 1.118379 0.093 Uiso 1 1 calc R U . . .
H9C H 0.031428 0.685674 1.147493 0.093 Uiso 1 1 calc R U . . .
C16 C -0.0867(3) 0.94611(18) 0.92071(16) 0.0637(6) Uani 1 1 d . . . . .
H16 H -0.086124 0.908559 0.985680 0.076 Uiso 1 1 calc R U . . .
C32 C 0.4018(3) 0.94275(17) 0.41094(17) 0.0654(6) Uani 1 1 d . . . . .
H32 H 0.338795 0.909976 0.472943 0.079 Uiso 1 1 calc R U . . .
C25 C 0.3087(4) 0.60744(19) 0.63518(15) 0.0680(6) Uani 1 1 d . . . . .
H25A H 0.297884 0.555624 0.698674 0.102 Uiso 1 1 calc R U . . .
H25B H 0.223714 0.666549 0.637926 0.102 Uiso 1 1 calc R U . . .
H25C H 0.422214 0.633701 0.614663 0.102 Uiso 1 1 calc R U . . .
C14 C -0.1537(4) 1.10887(19) 0.80140(19) 0.0734(7) Uani 1 1 d . . . . .
H14 H -0.195969 1.180715 0.785356 0.088 Uiso 1 1 calc R U . . .
C6 C 0.4385(3) 0.26532(18) 1.02036(19) 0.0691(6) Uani 1 1 d . . . . .
H6 H 0.472508 0.192611 1.043665 0.083 Uiso 1 1 calc R U . . .
C5 C 0.5050(3) 0.32273(19) 0.92395(18) 0.0666(6) Uani 1 1 d . . . . .
H5 H 0.582961 0.288471 0.883152 0.080 Uiso 1 1 calc R U . . .
C21 C 0.1543(3) 0.31589(19) 0.39324(19) 0.0709(7) Uani 1 1 d . . . . .
H21 H 0.136689 0.282955 0.349321 0.085 Uiso 1 1 calc R U . . .
C22 C 0.1387(3) 0.25886(18) 0.4910(2) 0.0735(7) Uani 1 1 d . . . . .
H22 H 0.108572 0.187785 0.512377 0.088 Uiso 1 1 calc R U . . .
C29 C 0.5880(4) 1.0425(2) 0.2298(2) 0.0791(8) Uani 1 1 d . . . . .
H29 H 0.650781 1.076368 0.167992 0.095 Uiso 1 1 calc R U . . .
C30 C 0.5167(4) 1.1011(2) 0.2934(3) 0.0897(10) Uani 1 1 d . . . . .
H30 H 0.531450 1.174506 0.275240 0.108 Uiso 1 1 calc R U . . .
C15 C -0.1535(4) 1.0519(2) 0.89719(18) 0.0769(7) Uani 1 1 d . . . . .
H15 H -0.198372 1.084637 0.946174 0.092 Uiso 1 1 calc R U . . .
C31 C 0.4246(4) 1.0515(2) 0.3831(2) 0.0806(8) Uani 1 1 d . . . . .
H31 H 0.376240 1.091340 0.426319 0.097 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 123.00(16) . . ?
C1 N1 N3 115.29(15) . . ?
C2 N1 N3 120.87(14) . . ?
C17 N4 C18 123.43(16) . . ?
C17 N4 N6 115.81(16) . . ?
C18 N4 N6 119.77(14) . . ?
C10 N3 N1 115.33(16) . . ?
C1 N2 C8 118.44(16) . . ?
C26 N6 N4 114.68(16) . . ?
C17 N5 C24 118.46(15) . . ?
C4 C3 C8 120.28(18) . . ?
C4 C3 C2 120.23(17) . . ?
C8 C3 C2 119.49(17) . . ?
N2 C1 N1 122.68(18) . . ?
N2 C1 C9 120.25(17) . . ?
N1 C1 C9 117.06(17) . . ?
C20 C19 C24 120.62(18) . . ?
C20 C19 C18 120.21(17) . . ?
C24 C19 C18 119.17(18) . . ?
N2 C8 C7 119.27(17) . . ?
N2 C8 C3 122.39(17) . . ?
C7 C8 C3 118.34(19) . . ?
N5 C24 C19 122.62(17) . . ?
N5 C24 C23 119.20(17) . . ?
C19 C24 C23 118.2(2) . . ?
O1 C2 N1 121.46(17) . . ?
O1 C2 C3 124.91(18) . . ?
N1 C2 C3 113.62(15) . . ?
O2 C18 N4 121.85(17) . . ?
O2 C18 C19 124.46(19) . . ?
N4 C18 C19 113.68(15) . . ?
C16 C11 C12 117.51(18) . . ?
C16 C11 C10 120.35(17) . . ?
C12 C11 C10 122.12(18) . . ?
N5 C17 N4 122.54(19) . . ?
N5 C17 C25 120.16(17) . . ?
N4 C17 C25 117.30(17) . . ?
N3 C10 C11 118.58(18) . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 Cl1 118.18(16) . . ?
C11 C12 Cl1 120.62(16) . . ?
C32 C27 C28 117.24(19) . . ?
C32 C27 C26 121.11(18) . . ?
C28 C27 C26 121.6(2) . . ?
N6 C26 C27 119.00(18) . . ?
C5 C4 C3 120.3(2) . . ?
C14 C13 C12 119.99(19) . . ?
C6 C7 C8 120.7(2) . . ?
C21 C20 C19 120.1(2) . . ?
C29 C28 C27 121.3(2) . . ?
C29 C28 Cl2 118.69(19) . . ?
C27 C28 Cl2 119.95(17) . . ?
C22 C23 C24 120.0(2) . . ?
C15 C16 C11 121.4(2) . . ?
C31 C32 C27 120.9(2) . . ?
C13 C14 C15 119.9(2) . . ?
C7 C6 C5 120.6(2) . . ?
C4 C5 C6 119.7(2) . . ?
C20 C21 C22 119.5(2) . . ?
C23 C22 C21 121.5(2) . . ?
C30 C29 C28 120.1(2) . . ?
C31 C30 C29 119.7(2) . . ?
C14 C15 C16 120.1(2) . . ?
C30 C31 C32 120.7(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C12 1.743(2) . ?
Cl2 C28 1.737(3) . ?
O1 C2 1.223(2) . ?
N1 C1 1.396(2) . ?
N1 C2 1.403(2) . ?
N1 N3 1.414(2) . ?
O2 C18 1.220(2) . ?
N4 C17 1.394(2) . ?
N4 C18 1.395(3) . ?
N4 N6 1.419(2) . ?
N3 C10 1.263(2) . ?
N2 C1 1.292(2) . ?
N2 C8 1.388(3) . ?
N6 C26 1.266(2) . ?
N5 C17 1.289(2) . ?
N5 C24 1.385(3) . ?
C3 C4 1.392(3) . ?
C3 C8 1.402(3) . ?
C3 C2 1.454(3) . ?
C1 C9 1.492(3) . ?
C19 C20 1.394(3) . ?
C19 C24 1.400(3) . ?
C19 C18 1.456(3) . ?
C8 C7 1.394(3) . ?
C24 C23 1.404(3) . ?
C11 C16 1.386(3) . ?
C11 C12 1.390(3) . ?
C11 C10 1.475(3) . ?
C17 C25 1.486(3) . ?
C12 C13 1.385(3) . ?
C27 C32 1.384(3) . ?
C27 C28 1.389(3) . ?
C27 C26 1.465(3) . ?
C4 C5 1.364(3) . ?
C13 C14 1.370(3) . ?
C7 C6 1.365(3) . ?
C20 C21 1.368(3) . ?
C28 C29 1.373(3) . ?
C23 C22 1.368(3) . ?
C16 C15 1.380(3) . ?
C32 C31 1.378(3) . ?
C14 C15 1.375(3) . ?
C6 C5 1.394(3) . ?
C21 C22 1.384(3) . ?
C29 C30 1.369(4) . ?
C30 C31 1.355(4) . ?
