#------------------------------------------------------------------------------
#$Date: 2025-11-12 03:11:17 +0100 (Wed 12 de Nov de 2025) $
#$Revision: 303272 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/08/7160846.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_7160846
loop_
_publ_author_name
'Farajpour, Behnaz'
'Khavari, Fatemeh'
'Davoudi, Nafiseh B.'
'Lotfi Nosood, Yazdanbakhsh'
'Notash, Behrouz'
'Taheri, Salman'
'Moradkhani, Fatemeh'
'Shiri, Morteza'
'Al-Harrasi, Ahmed'
'Hussain, Faiq'
_publ_section_title
;
 Synthesis of Furan-Linked Iminomethyl 2-Aminochromones via Base-Promoted
 Cascade Reaction of 3-Cyanochromones with β-Ketodinitriles
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01442E
_journal_year                    2025
_chemical_formula_moiety         'C21 H12 Cl N3 O3, C3 H7 N O'
_chemical_formula_sum            'C24 H19 Cl N4 O4'
_chemical_formula_weight         462.88
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_update_record
;
2025-08-03 deposited with the CCDC.	2025-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.37(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.683(3)
_cell_length_b                   8.7068(17)
_cell_length_c                   16.643(3)
_cell_measurement_reflns_used    4046
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.50
_cell_volume                     2307.2(8)
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_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  0.1615
_diffrn_reflns_av_sigmaI/netI    0.1572
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10979
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4046
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1995
_refine_ls_R_factor_gt           0.0843
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0645P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.1915
_reflns_number_gt                1732
_reflns_number_total             4046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5ob01442e2.cif
_cod_data_source_block           khc1991h
_cod_original_sg_symbol_Hall     '-P 2bc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160846
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.11921(11) 1.1077(3) 0.37030(15) 0.1309(8) Uani 1 1 d . . .
O1 O 0.49993(19) 0.7845(3) 0.46971(17) 0.0517(8) Uani 1 1 d . . .
O2 O 0.7834(2) 0.3696(4) 0.7132(2) 0.0708(10) Uani 1 1 d . . .
O3 O 0.5371(2) 0.4423(4) 0.6954(2) 0.0694(10) Uani 1 1 d . . .
O4 O 1.0599(3) 0.5668(8) 0.3915(4) 0.155(3) Uani 1 1 d . . .
N1 N 0.7256(3) 0.8060(6) 0.3545(3) 0.0965(17) Uani 1 1 d . . .
N2 N 0.6283(2) 0.6487(4) 0.5201(2) 0.0528(10) Uani 1 1 d . . .
N3 N 0.7775(3) 0.5154(6) 0.6026(3) 0.0703(13) Uani 1 1 d D . .
N4 N 0.9701(3) 0.7618(7) 0.3782(4) 0.0988(17) Uani 1 1 d . . .
C1 C 0.2204(3) 1.0423(7) 0.3800(4) 0.0743(16) Uani 1 1 d . . .
C2 C 0.2621(4) 1.0949(6) 0.3265(3) 0.0709(15) Uani 1 1 d . . .
H2 H 0.2362 1.1635 0.2837 0.085 Uiso 1 1 calc R . .
C3 C 0.2570(4) 0.9400(7) 0.4423(4) 0.0756(16) Uani 1 1 d . . .
H3 H 0.2279 0.9058 0.4786 0.091 Uiso 1 1 calc R . .
C4 C 0.3363(3) 0.8880(6) 0.4512(3) 0.0630(14) Uani 1 1 d . . .
H4 H 0.3606 0.8163 0.4927 0.076 Uiso 1 1 calc R . .
C5 C 0.3421(3) 1.0462(6) 0.3360(3) 0.0607(14) Uani 1 1 d . . .
H5 H 0.3710 1.0833 0.3002 0.073 Uiso 1 1 calc R . .
C6 C 0.3810(3) 0.9414(5) 0.3989(3) 0.0528(12) Uani 1 1 d . . .
C7 C 0.4664(3) 0.8887(5) 0.4068(3) 0.0509(12) Uani 1 1 d . . .
C8 C 0.5201(3) 0.9159(5) 0.3628(3) 0.0555(13) Uani 1 1 d . . .
H8 H 0.5118 0.9821 0.3172 0.067 Uiso 1 1 calc R . .
C9 C 0.5917(3) 0.8252(6) 0.3988(3) 0.0528(12) Uani 1 1 d D . .
C10 C 0.5781(3) 0.7458(5) 0.4648(3) 0.0468(11) Uani 1 1 d . . .
C11 C 0.6656(3) 0.8128(6) 0.3750(3) 0.0686(15) Uani 1 1 d D . .
C12 C 0.6018(3) 0.5828(5) 0.5782(3) 0.0533(13) Uani 1 1 d . . .
H12 H 0.5466 0.6011 0.5775 0.064 Uiso 1 1 calc R . .
C13 C 0.6509(3) 0.4860(5) 0.6419(3) 0.0501(12) Uani 1 1 d . . .
C14 C 0.7352(4) 0.4587(6) 0.6516(3) 0.0588(13) Uani 1 1 d . . .
C15 C 0.7476(4) 0.2956(6) 0.7687(3) 0.0672(15) Uani 1 1 d . . .
C16 C 0.6635(4) 0.3159(6) 0.7628(3) 0.0629(14) Uani 1 1 d . . .
C17 C 0.6118(4) 0.4183(5) 0.6999(3) 0.0558(13) Uani 1 1 d . . .
C18 C 0.6331(4) 0.2300(6) 0.8186(3) 0.0773(17) Uani 1 1 d . . .
H18 H 0.5770 0.2383 0.8165 0.093 Uiso 1 1 calc R . .
C19 C 0.6850(6) 0.1342(8) 0.8763(4) 0.102(2) Uani 1 1 d . . .
H19 H 0.6636 0.0768 0.9123 0.122 Uiso 1 1 calc R . .
C20 C 0.7675(5) 0.1223(8) 0.8813(4) 0.100(2) Uani 1 1 d . . .
H20 H 0.8026 0.0591 0.9219 0.120 Uiso 1 1 calc R . .
C21 C 0.7995(4) 0.2027(7) 0.8271(4) 0.0902(19) Uani 1 1 d . . .
H21 H 0.8559 0.1939 0.8302 0.108 Uiso 1 1 calc R . .
C22 C 0.9254(4) 0.8910(9) 0.3308(6) 0.140(3) Uani 1 1 d . . .
H22A H 0.9378 0.9819 0.3649 0.210 Uiso 1 1 calc R . .
H22B H 0.8661 0.8712 0.3148 0.210 Uiso 1 1 calc R . .
H22C H 0.9426 0.9055 0.2812 0.210 Uiso 1 1 calc R . .
C23 C 0.9533(6) 0.7265(14) 0.4542(7) 0.219(6) Uani 1 1 d . . .
H23A H 0.8981 0.6828 0.4420 0.328 Uiso 1 1 calc R . .
H23B H 0.9562 0.8185 0.4867 0.328 Uiso 1 1 calc R . .
H23C H 0.9941 0.6541 0.4856 0.328 Uiso 1 1 calc R . .
C24 C 1.0238(5) 0.6796(12) 0.3555(6) 0.134(3) Uani 1 1 d . . .
H24 H 1.0360 0.7096 0.3069 0.160 Uiso 1 1 calc R . .
H3A H 0.749(5) 0.572(8) 0.567(4) 0.160 Uiso 1 1 d D . .
H3B H 0.822(3) 0.482(9) 0.607(5) 0.160 Uiso 1 1 d D . .
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
C7 O1 C10 107.2(3) . . ?
C14 O2 C15 119.5(4) . . ?
C12 N2 C10 120.3(4) . . ?
C14 N3 H3A 112(6) . . ?
C14 N3 H3B 119(6) . . ?
H3A N3 H3B 128(8) . . ?
C24 N4 C23 119.0(8) . . ?
C24 N4 C22 124.2(7) . . ?
C23 N4 C22 116.8(7) . . ?
C2 C1 C3 121.1(5) . . ?
C2 C1 Cl1 119.9(5) . . ?
C3 C1 Cl1 119.0(5) . . ?
C1 C2 C5 119.5(5) . . ?
C1 C2 H2 120.3 . . ?
C5 C2 H2 120.3 . . ?
C4 C3 C1 119.9(5) . . ?
C4 C3 H3 120.0 . . ?
C1 C3 H3 120.0 . . ?
C3 C4 C6 120.4(5) . . ?
C3 C4 H4 119.8 . . ?
C6 C4 H4 119.8 . . ?
C2 C5 C6 120.8(5) . . ?
C2 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C4 C6 C5 118.3(5) . . ?
C4 C6 C7 122.0(5) . . ?
C5 C6 C7 119.7(4) . . ?
C8 C7 O1 110.3(4) . . ?
C8 C7 C6 133.5(4) . . ?
O1 C7 C6 116.1(4) . . ?
C7 C8 C9 106.9(4) . . ?
C7 C8 H8 126.6 . . ?
C9 C8 H8 126.6 . . ?
C10 C9 C11 123.7(5) . . ?
C10 C9 C8 107.5(4) . . ?
C11 C9 C8 128.8(4) . . ?
N2 C10 C9 130.4(4) . . ?
N2 C10 O1 121.5(4) . . ?
C9 C10 O1 108.1(4) . . ?
N1 C11 C9 178.3(6) . . ?
N2 C12 C13 124.6(5) . . ?
N2 C12 H12 117.7 . . ?
C13 C12 H12 117.7 . . ?
C14 C13 C12 122.2(4) . . ?
C14 C13 C17 119.8(5) . . ?
C12 C13 C17 118.0(5) . . ?
N3 C14 O2 112.1(5) . . ?
N3 C14 C13 124.9(5) . . ?
O2 C14 C13 122.9(5) . . ?
C21 C15 C16 122.8(6) . . ?
C21 C15 O2 116.1(6) . . ?
C16 C15 O2 121.1(5) . . ?
C15 C16 C18 116.3(5) . . ?
C15 C16 C17 120.0(5) . . ?
C18 C16 C17 123.7(5) . . ?
O3 C17 C13 122.5(5) . . ?
O3 C17 C16 121.0(5) . . ?
C13 C17 C16 116.5(5) . . ?
C19 C18 C16 120.9(6) . . ?
C19 C18 H18 119.5 . . ?
C16 C18 H18 119.5 . . ?
C20 C19 C18 120.4(7) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.5(7) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C15 C21 C20 119.0(7) . . ?
C15 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 H23A 109.5 . . ?
N4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C24 N4 126.3(9) . . ?
O4 C24 H24 116.9 . . ?
N4 C24 H24 116.9 . . ?
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 C1 1.743(6) . ?
O1 C7 1.371(5) . ?
O1 C10 1.374(5) . ?
O2 C14 1.345(6) . ?
O2 C15 1.399(6) . ?
O3 C17 1.245(6) . ?
O4 C24 1.212(9) . ?
N1 C11 1.152(6) . ?
N2 C12 1.311(5) . ?
N2 C10 1.343(5) . ?
N3 C14 1.323(7) . ?
N3 H3A 0.80(2) . ?
N3 H3B 0.78(2) . ?
N4 C24 1.288(9) . ?
N4 C23 1.408(8) . ?
N4 C22 1.447(8) . ?
C1 C2 1.363(7) . ?
C1 C3 1.364(7) . ?
C2 C5 1.364(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(7) . ?
C3 H3 0.9300 . ?
C4 C6 1.384(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.465(7) . ?
C7 C8 1.337(6) . ?
C8 C9 1.408(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(6) . ?
C9 C11 1.407(6) . ?
C12 C13 1.409(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(7) . ?
C13 C17 1.442(6) . ?
C15 C21 1.358(7) . ?
C15 C16 1.388(8) . ?
C16 C18 1.400(7) . ?
C16 C17 1.447(7) . ?
C18 C19 1.368(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(8) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 C5 -0.9(8) . . . . ?
Cl1 C1 C2 C5 178.2(4) . . . . ?
C2 C1 C3 C4 -0.5(9) . . . . ?
Cl1 C1 C3 C4 -179.7(4) . . . . ?
C1 C3 C4 C6 1.7(8) . . . . ?
C1 C2 C5 C6 1.1(8) . . . . ?
C3 C4 C6 C5 -1.5(7) . . . . ?
C3 C4 C6 C7 179.7(5) . . . . ?
C2 C5 C6 C4 0.0(7) . . . . ?
C2 C5 C6 C7 178.9(5) . . . . ?
C10 O1 C7 C8 0.3(5) . . . . ?
C10 O1 C7 C6 177.8(4) . . . . ?
C4 C6 C7 C8 176.3(5) . . . . ?
C5 C6 C7 C8 -2.5(8) . . . . ?
C4 C6 C7 O1 -0.6(6) . . . . ?
C5 C6 C7 O1 -179.4(4) . . . . ?
O1 C7 C8 C9 0.0(5) . . . . ?
C6 C7 C8 C9 -177.0(5) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C7 C8 C9 C11 179.8(5) . . . . ?
C12 N2 C10 C9 -178.9(5) . . . . ?
C12 N2 C10 O1 3.1(6) . . . . ?
C11 C9 C10 N2 2.2(8) . . . . ?
C8 C9 C10 N2 -177.7(4) . . . . ?
C11 C9 C10 O1 -179.7(5) . . . . ?
C8 C9 C10 O1 0.5(5) . . . . ?
C7 O1 C10 N2 177.9(4) . . . . ?
C7 O1 C10 C9 -0.5(5) . . . . ?
C10 C9 C11 N1 -161(23) . . . . ?
C8 C9 C11 N1 19(24) . . . . ?
C10 N2 C12 C13 -176.3(4) . . . . ?
N2 C12 C13 C14 3.9(7) . . . . ?
N2 C12 C13 C17 -178.1(4) . . . . ?
C15 O2 C14 N3 -177.5(4) . . . . ?
C15 O2 C14 C13 2.4(7) . . . . ?
C12 C13 C14 N3 -1.6(8) . . . . ?
C17 C13 C14 N3 -179.6(5) . . . . ?
C12 C13 C14 O2 178.4(4) . . . . ?
C17 C13 C14 O2 0.5(7) . . . . ?
C14 O2 C15 C21 177.4(4) . . . . ?
C14 O2 C15 C16 -1.8(7) . . . . ?
C21 C15 C16 C18 -2.4(8) . . . . ?
O2 C15 C16 C18 176.7(4) . . . . ?
C21 C15 C16 C17 179.1(5) . . . . ?
O2 C15 C16 C17 -1.7(7) . . . . ?
C14 C13 C17 O3 178.1(5) . . . . ?
C12 C13 C17 O3 0.1(7) . . . . ?
C14 C13 C17 C16 -3.8(6) . . . . ?
C12 C13 C17 C16 178.1(4) . . . . ?
C15 C16 C17 O3 -177.4(5) . . . . ?
C18 C16 C17 O3 4.2(7) . . . . ?
C15 C16 C17 C13 4.4(6) . . . . ?
C18 C16 C17 C13 -173.9(5) . . . . ?
C15 C16 C18 C19 1.1(7) . . . . ?
C17 C16 C18 C19 179.5(5) . . . . ?
C16 C18 C19 C20 1.0(9) . . . . ?
C18 C19 C20 C21 -1.9(11) . . . . ?
C16 C15 C21 C20 1.7(8) . . . . ?
O2 C15 C21 C20 -177.6(5) . . . . ?
C19 C20 C21 C15 0.6(10) . . . . ?
C23 N4 C24 O4 3.8(14) . . . . ?
C22 N4 C24 O4 -176.7(9) . . . . ?
