#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/94/1569407.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_1569407
loop_
_publ_author_name
'Chakraborty, Bimal Bhushan'
'Paul, Saurav'
'Anwar, Siddique'
'Choudhury, Sudip'
_publ_section_title
;
 2-Amino-4-(4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile
 acetic acid monosolvate
;
_journal_coeditor_code           HB4427
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x230558
_journal_paper_doi               10.1107/S2414314623005588
_journal_volume                  8
_journal_year                    2023
_chemical_formula_iupac          'C20 H14 N2 O4, C2 H4 O2'
_chemical_formula_moiety         'C20 H14 N2 O4, C2 H4 O2'
_chemical_formula_sum            'C22 H18 N2 O6'
_chemical_formula_weight         406.38
_chemical_melting_point          511.15
_chemical_name_systematic
'2-Amino-4-(4-methoxyphenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile acetic acid monosolvate'
_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     iterative
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                82.468(4)
_cell_angle_beta                 77.379(4)
_cell_angle_gamma                73.419(4)
_cell_formula_units_Z            2
_cell_length_a                   7.9303(6)
_cell_length_b                   11.2977(9)
_cell_length_c                   11.9988(9)
_cell_measurement_reflns_used    5371
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.66
_cell_volume                     1002.71(14)
_computing_cell_refinement
;
APEX2 (Bruker 2015)
;
_computing_data_collection
;
SAINT (Bruker 2015)
;
_computing_data_reduction
;
SAINT (Bruker 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009; Bourhis et al.,
2015)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009; Bourhis et al.,
2015)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17101
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.062
_diffrn_reflns_theta_min         2.730
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       Block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.245
_refine_ls_extinction_coef       0.037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0503
_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)+(0.0858P)²+0.1068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1571
_reflns_number_gt                3457
_reflns_number_total             4807
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4427.cif
_cod_data_source_block           I
_cod_database_code               1569407
#BEGIN Tags that were not found in dictionaries:
_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.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.28503(19) 0.15224(13) 0.94770(12) 0.0398(3) Uani d 1 . .
C C2 0.46268(18) 0.13992(12) 0.87929(11) 0.0343(3) Uani d 1 . .
C C3 0.59600(18) 0.14624(12) 0.92882(11) 0.0351(3) Uani d 1 . .
C C4 0.5684(2) 0.16975(12) 1.04776(11) 0.0388(3) Uani d 1 . .
C C5 0.3950(2) 0.18548(13) 1.10966(11) 0.0416(3) Uani d 1 . .
C C6 0.7039(2) 0.17741(15) 1.10147(13) 0.0506(4) Uani d 1 . .
H H4 0.820649 0.167223 1.060769 0.061 Uiso calc 1 . .
C C7 0.6624(3) 0.20027(18) 1.21552(15) 0.0649(5) Uani d 1 . .
H H3 0.752115 0.204468 1.252281 0.078 Uiso calc 1 . .
C C8 0.4892(3) 0.21697(18) 1.27573(14) 0.0662(5) Uani d 1 . .
H H2 0.463455 0.233314 1.352487 0.079 Uiso calc 1 . .
C C9 0.3539(3) 0.20992(16) 1.22439(13) 0.0566(4) Uani d 1 . .
H H1 0.237323 0.221273 1.265566 0.068 Uiso calc 1 . .
C C10 0.81505(19) 0.09187(13) 0.76421(11) 0.0372(3) Uani d 1 . .
C C11 0.69033(18) 0.08117(12) 0.70792(11) 0.0350(3) Uani d 1 . .
C C12 0.49036(17) 0.12492(12) 0.75303(10) 0.0339(3) Uani d 1 . .
H H5 0.434598 0.060982 0.742969 0.041 Uiso calc 1 . .
C C13 0.74784(19) 0.03627(13) 0.59735(12) 0.0414(3) Uani d 1 . .
C C14 0.40507(17) 0.24512(12) 0.68869(10) 0.0345(3) Uani d 1 . .
C C15 0.4317(2) 0.35587(13) 0.70738(13) 0.0471(4) Uani d 1 . .
H H6 0.499634 0.356797 0.761194 0.056 Uiso calc 1 . .
C C16 0.3594(2) 0.46567(14) 0.64780(14) 0.0506(4) Uani d 1 . .
H H7 0.378473 0.539410 0.661815 0.061 Uiso calc 1 . .
C C17 0.2593(2) 0.46490(14) 0.56784(13) 0.0478(4) Uani d 1 . .
C C18 0.2344(2) 0.35441(16) 0.54666(14) 0.0506(4) Uani d 1 . .
H H8 0.168538 0.353381 0.491619 0.061 Uiso calc 1 . .
C C19 0.3064(2) 0.24558(14) 0.60666(12) 0.0423(3) Uani d 1 . .
H H9 0.288535 0.171768 0.591792 0.051 Uiso calc 1 . .
C C20 0.1897(3) 0.68441(18) 0.5279(2) 0.0792(6) Uani d 1 . .
H H12 0.134892 0.699323 0.606260 0.119 Uiso calc 1 . .
H H13 0.127714 0.747593 0.478338 0.119 Uiso calc 1 . .
H H14 0.312930 0.685832 0.515177 0.119 Uiso calc 1 . .
N N1 0.99246(18) 0.06727(16) 0.73010(13) 0.0548(4) Uani d 1 . .
H H11 1.045(3) 0.044(2) 0.664(2) 0.082 Uiso d 1 . .
H H10 1.050(3) 0.0795(18) 0.7738(17) 0.063(6) Uiso d 1 . .
N N2 0.7914(2) 0.00034(16) 0.50810(12) 0.0636(4) Uani d 1 . .
O O1 0.15733(14) 0.14244(11) 0.91391(10) 0.0554(3) Uani d 1 . .
O O2 0.25831(14) 0.17565(10) 1.06096(8) 0.0469(3) Uani d 1 . .
O O3 0.76834(13) 0.13240(10) 0.87243(8) 0.0438(3) Uani d 1 . .
O O4 0.18023(18) 0.56733(12) 0.50445(12) 0.0718(4) Uani d 1 . .
C C21 0.7402(3) 0.47407(18) 0.9117(2) 0.0699(5) Uani d 1 . .
C C22 0.9237(4) 0.4564(3) 0.8413(3) 0.1178(10) Uani d 1 . .
H H16 0.917608 0.462359 0.761649 0.177 Uiso calc 1 . .
H H17 0.974923 0.519298 0.855137 0.177 Uiso calc 1 . .
H H18 0.997116 0.376303 0.861655 0.177 Uiso calc 1 . .
O O5 0.6192(2) 0.4549(2) 0.87859(14) 0.1048(6) Uani d 1 . .
O O6 0.7183(3) 0.51493(19) 1.01024(16) 0.0988(6) Uani d 1 . .
H H15 0.594(5) 0.518(3) 1.052(3) 0.139(11) Uiso d 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'
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
O1 C1 C2 . . 125.22(13) ?
O1 C1 O2 . . 116.85(13) ?
O2 C1 C2 . . 117.93(12) ?
C1 C2 C12 . . 118.49(12) ?
C3 C2 C1 . . 119.38(12) ?
C3 C2 C12 . . 122.09(12) ?
C2 C3 C4 . . 122.65(13) ?
C2 C3 O3 . . 123.72(11) ?
O3 C3 C4 . . 113.62(12) ?
C5 C4 C3 . . 116.32(13) ?
C5 C4 C6 . . 119.71(13) ?
C6 C4 C3 . . 123.98(14) ?
C4 C5 C9 . . 120.82(15) ?
O2 C5 C4 . . 121.65(12) ?
O2 C5 C9 . . 117.52(14) ?
C4 C6 H4 . . 120.5 ?
C7 C6 C4 . . 119.07(16) ?
C7 C6 H4 . . 120.5 ?
C6 C7 H3 . . 119.7 ?
C6 C7 C8 . . 120.64(17) ?
C8 C7 H3 . . 119.7 ?
C7 C8 H2 . . 119.4 ?
C9 C8 C7 . . 121.17(15) ?
C9 C8 H2 . . 119.4 ?
C5 C9 H1 . . 120.7 ?
C8 C9 C5 . . 118.59(17) ?
C8 C9 H1 . . 120.7 ?
C11 C10 O3 . . 121.49(12) ?
N1 C10 C11 . . 129.17(13) ?
N1 C10 O3 . . 109.34(12) ?
C10 C11 C12 . . 123.19(11) ?
C10 C11 C13 . . 118.66(12) ?
C13 C11 C12 . . 117.94(12) ?
C2 C12 C11 . . 107.92(10) ?
C2 C12 H5 . . 108.6 ?
C2 C12 C14 . . 111.51(10) ?
C11 C12 H5 . . 108.6 ?
C11 C12 C14 . . 111.56(10) ?
C14 C12 H5 . . 108.6 ?
N2 C13 C11 . . 178.91(16) ?
C15 C14 C12 . . 120.49(12) ?
C15 C14 C19 . . 118.23(13) ?
C19 C14 C12 . . 121.21(12) ?
C14 C15 H6 . . 119.2 ?
C14 C15 C16 . . 121.51(13) ?
C16 C15 H6 . . 119.2 ?
C15 C16 H7 . . 120.2 ?
C17 C16 C15 . . 119.55(14) ?
C17 C16 H7 . . 120.2 ?
C16 C17 C18 . . 119.60(14) ?
O4 C17 C16 . . 124.86(15) ?
O4 C17 C18 . . 115.54(14) ?
C17 C18 H8 . . 119.8 ?
C19 C18 C17 . . 120.42(13) ?
C19 C18 H8 . . 119.8 ?
C14 C19 H9 . . 119.7 ?
C18 C19 C14 . . 120.67(13) ?
C18 C19 H9 . . 119.7 ?
H12 C20 H13 . . 109.5 ?
H12 C20 H14 . . 109.5 ?
H13 C20 H14 . . 109.5 ?
O4 C20 H12 . . 109.5 ?
O4 C20 H13 . . 109.5 ?
O4 C20 H14 . . 109.5 ?
C10 N1 H11 . . 122.0(16) ?
C10 N1 H10 . . 117.6(14) ?
H11 N1 H10 . . 120(2) ?
C5 O2 C1 . . 121.99(11) ?
C3 O3 C10 . . 118.34(11) ?
C17 O4 C20 . . 118.28(15) ?
O5 C21 C22 . . 123.0(2) ?
O5 C21 O6 . . 121.7(2) ?
O6 C21 C22 . . 115.3(2) ?
C21 C22 H16 . . 109.5 ?
C21 C22 H17 . . 109.5 ?
C21 C22 H18 . . 109.5 ?
H17 C22 H16 . . 109.5 ?
H18 C22 H16 . . 109.5 ?
H18 C22 H17 . . 109.5 ?
C21 O6 H15 . . 108.3(19) ?
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
C2 C1 . 1.4459(19) ?
C2 C3 . 1.3435(19) ?
C3 C4 . 1.4439(18) ?
C4 C6 . 1.396(2) ?
C5 C4 . 1.387(2) ?
C5 C9 . 1.389(2) ?
C6 H4 . 0.9300 ?
C7 C6 . 1.377(2) ?
C7 H3 . 0.9300 ?
C8 C7 . 1.378(3) ?
C8 H2 . 0.9300 ?
C9 C8 . 1.374(3) ?
C9 H1 . 0.9300 ?
C11 C10 . 1.3529(19) ?
C11 C13 . 1.4161(18) ?
C12 C2 . 1.5075(17) ?
C12 C11 . 1.5165(18) ?
C12 H5 . 0.9800 ?
C14 C12 . 1.5253(18) ?
C14 C15 . 1.380(2) ?
C15 H6 . 0.9300 ?
C15 C16 . 1.385(2) ?
C16 H7 . 0.9300 ?
C17 C16 . 1.375(2) ?
C17 C18 . 1.381(2) ?
C18 H8 . 0.9300 ?
C18 C19 . 1.380(2) ?
C19 C14 . 1.3834(19) ?
C19 H9 . 0.9300 ?
C20 H12 . 0.9600 ?
C20 H13 . 0.9600 ?
C20 H14 . 0.9600 ?
N1 C10 . 1.3339(19) ?
N1 H11 . 0.85(2) ?
N1 H10 . 0.81(2) ?
N2 C13 . 1.1416(18) ?
O1 C1 . 1.2072(17) ?
O2 C1 . 1.3776(17) ?
O2 C5 . 1.3753(18) ?
O3 C3 . 1.3608(16) ?
O3 C10 . 1.3718(15) ?
O4 C17 . 1.3691(18) ?
O4 C20 . 1.414(2) ?
C22 C21 . 1.488(3) ?
C22 H16 . 0.9600 ?
C22 H17 . 0.9600 ?
C22 H18 . 0.9600 ?
O5 C21 . 1.197(3) ?
O6 C21 . 1.284(3) ?
O6 H15 . 1.00(4) ?
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 H11 N2 2_756 0.85(2) 2.22(2) 3.062(2) 172(2)
N1 H10 O1 1_655 0.81(2) 2.31(2) 3.111(2) 168(2)
O6 H15 O5 2_667 1.00(4) 1.67(4) 2.664(3) 172(3)
C15 H6 O5 1_555 0.93 2.39 3.251(2) 154
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C4 . . . . -2.4(2) ?
C1 C2 C3 O3 . . . . 178.15(12) ?
C1 O2 C5 C4 . . . . -1.4(2) ?
C1 O2 C5 C9 . . . . 179.66(13) ?
C2 C3 C4 C5 . . . . 0.2(2) ?
C2 C3 C4 C6 . . . . -179.69(13) ?
C2 C12 C11 C10 . . . . -18.04(17) ?
C2 C12 C11 C13 . . . . 167.21(11) ?
C3 C2 C1 O1 . . . . -176.40(14) ?
C3 C2 C1 O2 . . . . 2.84(19) ?
C3 C4 C6 C7 . . . . 179.99(14) ?
C3 O3 C10 C11 . . . . 8.62(19) ?
C3 O3 C10 N1 . . . . -171.14(12) ?
C4 C5 C9 C8 . . . . -0.7(2) ?
C5 C4 C6 C7 . . . . 0.2(2) ?
C5 C9 C8 C7 . . . . 0.0(3) ?
C5 O2 C1 C2 . . . . -0.99(19) ?
C5 O2 C1 O1 . . . . 178.31(12) ?
C8 C7 C6 C4 . . . . -0.8(3) ?
C9 C5 C4 C3 . . . . -179.26(12) ?
C9 C5 C4 C6 . . . . 0.6(2) ?
C9 C8 C7 C6 . . . . 0.8(3) ?
C10 O3 C3 C2 . . . . -10.0(2) ?
C10 O3 C3 C4 . . . . 170.56(11) ?
C11 C12 C2 C1 . . . . -165.55(11) ?
C11 C12 C2 C3 . . . . 16.70(17) ?
C12 C2 C1 O1 . . . . 5.8(2) ?
C12 C2 C1 O2 . . . . -174.98(11) ?
C12 C2 C3 C4 . . . . 175.29(11) ?
C12 C2 C3 O3 . . . . -4.1(2) ?
C12 C11 C10 N1 . . . . -173.68(14) ?
C12 C11 C10 O3 . . . . 6.6(2) ?
C12 C14 C15 C16 . . . . 178.31(14) ?
C13 C11 C10 N1 . . . . 1.0(2) ?
C13 C11 C10 O3 . . . . -178.68(12) ?
C14 C12 C2 C1 . . . . 71.60(15) ?
C14 C12 C2 C3 . . . . -106.15(14) ?
C14 C12 C11 C10 . . . . 104.78(14) ?
C14 C12 C11 C13 . . . . -69.97(15) ?
C14 C15 C16 C17 . . . . -0.2(3) ?
C15 C14 C12 C2 . . . . 47.04(17) ?
C15 C14 C12 C11 . . . . -73.70(16) ?
C16 C17 C18 C19 . . . . 1.2(3) ?
C17 C18 C19 C14 . . . . -0.1(2) ?
C18 C17 C16 C15 . . . . -1.0(3) ?
C18 C19 C14 C12 . . . . -178.09(13) ?
C18 C19 C14 C15 . . . . -1.0(2) ?
C19 C14 C12 C2 . . . . -135.97(13) ?
C19 C14 C12 C11 . . . . 103.28(14) ?
C19 C14 C15 C16 . . . . 1.2(2) ?
C20 O4 C17 C16 . . . . -5.0(3) ?
C20 O4 C17 C18 . . . . 175.46(17) ?
O2 C5 C4 C3 . . . . 1.79(19) ?
O2 C5 C4 C6 . . . . -178.36(13) ?
O2 C5 C9 C8 . . . . 178.34(14) ?
O3 C3 C4 C5 . . . . 179.61(12) ?
O3 C3 C4 C6 . . . . -0.2(2) ?
O4 C17 C16 C15 . . . . 179.48(15) ?
O4 C17 C18 C19 . . . . -179.25(14) ?
