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#$Date: 2025-01-22 04:14:03 +0200 (Wed, 22 Jan 2025) $
#$Revision: 297407 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/98/7249817.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_7249817
loop_
_publ_author_name
'Aly, Ashraf A.'
'Abd El-Naby, Hisham A.'
'Ahmed, Essam Kh.'
'Gedamy, Sageda A.'
'Rissanen, Kari'
'Nieger, Martin'
'Brown, Alan B.'
'Shehat, Michael G.'
'Shaaban, Marwa M.'
'Atta, Amal'
_publ_section_title
;
 Microwave-assisted synthesis and in vitro and in silico studies of
 pyrano[3,2-c]quinoline-3-carboxylates as dual acting anti-cancer and
 anti-microbial agents and potential topoisomerase II and DNA-gyrase
 inhibitors
;
_journal_issue                   3
_journal_name_full               'RSC Advances'
_journal_page_first              1941
_journal_page_last               1956
_journal_paper_doi               10.1039/D4RA06201A
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C19 H16 N2 O5'
_chemical_formula_sum            'C19 H16 N2 O5'
_chemical_formula_weight         352.34
_chemical_name_systematic
'ethyl 2-amino-4-(furan-2-yl)-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate'
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-12-07 deposited with the CCDC.	2024-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                106.141(3)
_cell_angle_beta                 103.673(2)
_cell_angle_gamma                100.320(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2266(2)
_cell_length_b                   8.5847(3)
_cell_length_c                   12.5866(3)
_cell_measurement_reflns_used    10226
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      78.3
_cell_measurement_theta_min      3.8
_cell_volume                     800.60(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'omega scans, 0.5 deg.'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17010
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.251
_diffrn_reflns_theta_min         3.836
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.895
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       blocks
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3430
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0393
_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)+(0.0651P)²+0.2659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3087
_reflns_number_total             3430
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra06201a2.cif
_cod_data_source_block           sb1526_hy_compound_3a
_cod_database_code               7249817
_shelx_shelxl_version_number     2014/7
_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   0.913
_shelx_estimated_absorpt_t_max   0.968
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
O1 O 0.69097(12) 0.53171(11) 0.48221(7) 0.0223(2) Uani 1 1 d . . . . .
C2 C 0.71392(16) 0.63514(15) 0.59278(11) 0.0209(3) Uani 1 1 d . . . . .
N2 N 0.66369(16) 0.77405(14) 0.58790(10) 0.0258(2) Uani 1 1 d D . . . .
H2A H 0.620(2) 0.779(2) 0.5192(13) 0.039 Uiso 1 1 d D U . . .
H2B H 0.675(3) 0.844(2) 0.6552(13) 0.039 Uiso 1 1 d D U . . .
C3 C 0.77860(16) 0.59578(15) 0.68877(11) 0.0210(3) Uani 1 1 d . . . . .
C4 C 0.82658(16) 0.43071(15) 0.67970(10) 0.0201(3) Uani 1 1 d . . . . .
H4 H 0.9442 0.4559 0.7359 0.024 Uiso 1 1 calc R U . . .
C4A C 0.83665(16) 0.35131(15) 0.55902(10) 0.0202(3) Uani 1 1 d . . . . .
C5 C 0.92262(16) 0.21661(15) 0.53878(11) 0.0209(3) Uani 1 1 d . . . . .
O5 O 0.99473(12) 0.16854(12) 0.61791(8) 0.0255(2) Uani 1 1 d . . . . .
N6 N 0.92153(14) 0.14386(14) 0.42738(9) 0.0228(2) Uani 1 1 d D . . . .
H6 H 0.963(2) 0.0529(19) 0.4150(14) 0.027 Uiso 1 1 d D U . . .
C6A C 0.84240(16) 0.18600(16) 0.33394(11) 0.0215(3) Uani 1 1 d . . . . .
C7 C 0.84347(17) 0.09928(17) 0.22192(12) 0.0251(3) Uani 1 1 d . . . . .
H7 H 0.9005 0.0119 0.2100 0.030 Uiso 1 1 calc R U . . .
C8 C 0.76135(19) 0.14160(17) 0.12934(12) 0.0276(3) Uani 1 1 d . . . . .
H8 H 0.7626 0.0835 0.0535 0.033 Uiso 1 1 calc R U . . .
C9 C 0.67596(19) 0.26953(18) 0.14602(12) 0.0285(3) Uani 1 1 d . . . . .
H9 H 0.6173 0.2955 0.0812 0.034 Uiso 1 1 calc R U . . .
C10 C 0.67651(18) 0.35801(16) 0.25588(11) 0.0253(3) Uani 1 1 d . . . . .
H10 H 0.6204 0.4462 0.2668 0.030 Uiso 1 1 calc R U . . .
C10A C 0.76029(16) 0.31738(15) 0.35161(11) 0.0210(3) Uani 1 1 d . . . . .
C10B C 0.76528(15) 0.39932(15) 0.46920(11) 0.0200(3) Uani 1 1 d . . . . .
C11 C 0.79351(16) 0.71125(16) 0.80144(11) 0.0225(3) Uani 1 1 d . . . . .
O11 O 0.76573(13) 0.85065(11) 0.82169(8) 0.0271(2) Uani 1 1 d . . . . .
O12 O 0.84011(14) 0.64453(12) 0.88501(8) 0.0280(2) Uani 1 1 d . . . . .
C13 C 0.8435(2) 0.73979(18) 1.00040(12) 0.0320(3) Uani 1 1 d . . . . .
H13A H 0.7488 0.7967 0.9964 0.038 Uiso 1 1 calc R U . . .
H13B H 0.9555 0.8261 1.0409 0.038 Uiso 1 1 calc R U . . .
C14 C 0.8206(2) 0.6172(2) 1.06328(14) 0.0402(4) Uani 1 1 d . . . . .
H14A H 0.8221 0.6767 1.1423 0.060 Uiso 1 1 calc R U . . .
H14B H 0.7094 0.5326 1.0223 0.060 Uiso 1 1 calc R U . . .
H14C H 0.9151 0.5619 1.0665 0.060 Uiso 1 1 calc R U . . .
C15 C 0.70184(16) 0.31039(15) 0.70926(10) 0.0204(3) Uani 1 1 d . . . . .
C16 C 0.71939(18) 0.19775(17) 0.76441(12) 0.0280(3) Uani 1 1 d . . . . .
H16 H 0.8242 0.1723 0.7958 0.034 Uiso 1 1 calc R U . . .
C17 C 0.55060(19) 0.12357(17) 0.76681(12) 0.0285(3) Uani 1 1 d . . . . .
H17 H 0.5215 0.0401 0.8003 0.034 Uiso 1 1 calc R U . . .
C18 C 0.44193(19) 0.19558(18) 0.71223(13) 0.0300(3) Uani 1 1 d . . . . .
H18 H 0.3205 0.1705 0.7007 0.036 Uiso 1 1 calc R U . . .
O19 O 0.53085(12) 0.31074(12) 0.67537(8) 0.0273(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10B O1 C2 118.28(10) . . ?
N2 C2 C3 127.76(12) . . ?
N2 C2 O1 109.41(11) . . ?
C3 C2 O1 122.83(11) . . ?
C2 N2 H2A 117.3(13) . . ?
C2 N2 H2B 113.3(13) . . ?
H2A N2 H2B 129.3(18) . . ?
C2 C3 C11 118.64(11) . . ?
C2 C3 C4 121.46(11) . . ?
C11 C3 C4 119.84(11) . . ?
C15 C4 C4A 110.50(10) . . ?
C15 C4 C3 112.59(10) . . ?
C4A C4 C3 109.47(10) . . ?
C15 C4 H4 108.0 . . ?
C4A C4 H4 108.0 . . ?
C3 C4 H4 108.0 . . ?
C10B C4A C5 119.18(11) . . ?
C10B C4A C4 121.98(11) . . ?
C5 C4A C4 118.82(11) . . ?
O5 C5 N6 120.71(11) . . ?
O5 C5 C4A 122.68(11) . . ?
N6 C5 C4A 116.62(11) . . ?
C5 N6 C6A 124.91(11) . . ?
C5 N6 H6 115.2(11) . . ?
C6A N6 H6 119.3(11) . . ?
N6 C6A C7 120.48(11) . . ?
N6 C6A C10A 119.47(11) . . ?
C7 C6A C10A 120.04(12) . . ?
C8 C7 C6A 119.61(12) . . ?
C8 C7 H7 120.2 . . ?
C6A C7 H7 120.2 . . ?
C7 C8 C9 120.60(12) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 120.46(13) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C10A 119.83(12) . . ?
C9 C10 H10 120.1 . . ?
C10A C10 H10 120.1 . . ?
C10 C10A C6A 119.43(12) . . ?
C10 C10A C10B 124.22(11) . . ?
C6A C10A C10B 116.33(11) . . ?
C4A C10B O1 122.80(11) . . ?
C4A C10B C10A 123.36(11) . . ?
O1 C10B C10A 113.83(10) . . ?
O11 C11 O12 122.53(11) . . ?
O11 C11 C3 126.63(12) . . ?
O12 C11 C3 110.83(10) . . ?
C11 O12 C13 116.62(10) . . ?
O12 C13 C14 106.71(11) . . ?
O12 C13 H13A 110.4 . . ?
C14 C13 H13A 110.4 . . ?
O12 C13 H13B 110.4 . . ?
C14 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 O19 109.48(11) . . ?
C16 C15 C4 134.10(12) . . ?
O19 C15 C4 116.42(10) . . ?
C15 C16 C17 107.20(12) . . ?
C15 C16 H16 126.4 . . ?
C17 C16 H16 126.4 . . ?
C18 C17 C16 106.12(12) . . ?
C18 C17 H17 126.9 . . ?
C16 C17 H17 126.9 . . ?
C17 C18 O19 110.44(12) . . ?
C17 C18 H18 124.8 . . ?
O19 C18 H18 124.8 . . ?
C15 O19 C18 106.75(10) . . ?
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
O1 C10B 1.3730(14) . ?
O1 C2 1.3746(15) . ?
C2 N2 1.3423(16) . ?
C2 C3 1.3580(17) . ?
N2 H2A 0.873(14) . ?
N2 H2B 0.863(14) . ?
C3 C11 1.4496(17) . ?
C3 C4 1.5195(16) . ?
C4 C15 1.5076(17) . ?
C4 C4A 1.5109(16) . ?
C4 H4 1.0000 . ?
C4A C10B 1.3507(17) . ?
C4A C5 1.4549(16) . ?
C5 O5 1.2454(15) . ?
C5 N6 1.3642(16) . ?
N6 C6A 1.3773(16) . ?
N6 H6 0.896(14) . ?
C6A C7 1.4024(17) . ?
C6A C10A 1.4080(17) . ?
C7 C8 1.3774(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.401(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3787(19) . ?
C9 H9 0.9500 . ?
C10 C10A 1.4056(17) . ?
C10 H10 0.9500 . ?
C10A C10B 1.4384(17) . ?
C11 O11 1.2269(16) . ?
C11 O12 1.3433(15) . ?
O12 C13 1.4461(16) . ?
C13 C14 1.494(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.3467(18) . ?
C15 O19 1.3708(15) . ?
C16 C17 1.4312(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.341(2) . ?
C17 H17 0.9500 . ?
C18 O19 1.3726(16) . ?
C18 H18 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O19 0.873(14) 2.301(15) 3.1315(15) 158.8(17) 2_666
N2 H2B O11 0.863(14) 2.031(17) 2.7119(15) 135.2(17) .
N6 H6 O5 0.896(14) 1.942(14) 2.8266(14) 168.6(16) 2_756
C18 H18 O5 0.95 2.63 3.5318(17) 158.4 1_455
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
C10B O1 C2 N2 167.53(11) . . . . ?
C10B O1 C2 C3 -12.31(17) . . . . ?
N2 C2 C3 C11 1.8(2) . . . . ?
O1 C2 C3 C11 -178.36(11) . . . . ?
N2 C2 C3 C4 178.78(12) . . . . ?
O1 C2 C3 C4 -1.42(19) . . . . ?
C2 C3 C4 C15 -108.31(13) . . . . ?
C11 C3 C4 C15 68.60(15) . . . . ?
C2 C3 C4 C4A 15.02(16) . . . . ?
C11 C3 C4 C4A -168.07(11) . . . . ?
C15 C4 C4A C10B 107.58(13) . . . . ?
C3 C4 C4A C10B -16.97(16) . . . . ?
C15 C4 C4A C5 -71.04(14) . . . . ?
C3 C4 C4A C5 164.41(11) . . . . ?
C10B C4A C5 O5 178.27(12) . . . . ?
C4 C4A C5 O5 -3.07(18) . . . . ?
C10B C4A C5 N6 -1.53(18) . . . . ?
C4 C4A C5 N6 177.13(11) . . . . ?
O5 C5 N6 C6A 178.63(11) . . . . ?
C4A C5 N6 C6A -1.57(19) . . . . ?
C5 N6 C6A C7 -177.70(11) . . . . ?
C5 N6 C6A C10A 2.40(19) . . . . ?
N6 C6A C7 C8 179.02(12) . . . . ?
C10A C6A C7 C8 -1.08(19) . . . . ?
C6A C7 C8 C9 -0.4(2) . . . . ?
C7 C8 C9 C10 1.6(2) . . . . ?
C8 C9 C10 C10A -1.3(2) . . . . ?
C9 C10 C10A C6A -0.2(2) . . . . ?
C9 C10 C10A C10B -178.63(12) . . . . ?
N6 C6A C10A C10 -178.71(11) . . . . ?
C7 C6A C10A C10 1.39(19) . . . . ?
N6 C6A C10A C10B -0.15(18) . . . . ?
C7 C6A C10A C10B 179.94(11) . . . . ?
C5 C4A C10B O1 -176.04(11) . . . . ?
C4 C4A C10B O1 5.34(19) . . . . ?
C5 C4A C10B C10A 3.81(19) . . . . ?
C4 C4A C10B C10A -174.81(11) . . . . ?
C2 O1 C10B C4A 10.35(17) . . . . ?
C2 O1 C10B C10A -169.52(10) . . . . ?
C10 C10A C10B C4A 175.52(12) . . . . ?
C6A C10A C10B C4A -2.95(19) . . . . ?
C10 C10A C10B O1 -4.61(18) . . . . ?
C6A C10A C10B O1 176.91(10) . . . . ?
C2 C3 C11 O11 -6.0(2) . . . . ?
C4 C3 C11 O11 177.00(12) . . . . ?
C2 C3 C11 O12 172.78(11) . . . . ?
C4 C3 C11 O12 -4.22(17) . . . . ?
O11 C11 O12 C13 4.61(19) . . . . ?
C3 C11 O12 C13 -174.23(11) . . . . ?
C11 O12 C13 C14 155.70(13) . . . . ?
C4A C4 C15 C16 93.93(17) . . . . ?
C3 C4 C15 C16 -143.32(15) . . . . ?
C4A C4 C15 O19 -86.57(12) . . . . ?
C3 C4 C15 O19 36.18(14) . . . . ?
O19 C15 C16 C17 -0.62(15) . . . . ?
C4 C15 C16 C17 178.90(13) . . . . ?
C15 C16 C17 C18 0.39(16) . . . . ?
C16 C17 C18 O19 -0.02(16) . . . . ?
C16 C15 O19 C18 0.61(14) . . . . ?
C4 C15 O19 C18 -179.01(11) . . . . ?
C17 C18 O19 C15 -0.35(15) . . . . ?
