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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/28/1542801.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_1542801
loop_
_publ_author_name
'Dubey, Ritesh'
'Desiraju, Gautam R.'
_publ_section_title
;
 Combinatorial selection of molecular conformations and supramolecular
 synthons in quercetin cocrystal landscapes: a route to ternary solids
;
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first              402
_journal_page_last               408
_journal_paper_doi               10.1107/S2052252515009884
_journal_volume                  2
_journal_year                    2015
_chemical_formula_sum            'C25 H18 N4 O7'
_chemical_formula_weight         486.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 101.543(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.647(3)
_cell_length_b                   12.8623(16)
_cell_length_c                   15.712(2)
_cell_measurement_temperature    150(2)
_cell_volume                     4286.2(10)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24298
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.852
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Bruker, AXS, 2008'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       Plate
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0517
_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)+(0.0625P)²+17.9666P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3253
_reflns_number_total             4173
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {ca7e82c3-76a5-4cc8-8d7a-5838d2425dc3}
_cod_data_source_file            lc5063.cif
_cod_data_source_block           QAP_II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Analytical' changed to
'analytical' according to
/usr/data/users/saulius/automatic-downloads/current/IUCr/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4287 2015-11-16 14:04:37Z antanas 
;
_cod_database_code               1542801
_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   0.962
_shelx_estimated_absorpt_t_max   0.983
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
H1O H 0.1751(17) 0.477(3) 0.369(2) 0.051(10) Uiso 1 1 d . .
H4O H 0.0968(16) 0.276(3) -0.149(2) 0.046(10) Uiso 1 1 d . .
H2O H 0.2322(15) 0.314(2) 0.067(2) 0.039(9) Uiso 1 1 d . .
H5O H -0.1895(18) 0.236(3) -0.290(2) 0.052(10) Uiso 1 1 d . .
H6O H -0.268(2) 0.361(3) -0.180(3) 0.076(13) Uiso 1 1 d . .
O7 O 0.01858(7) 0.38411(12) 0.05880(10) 0.0156(4) Uani 1 1 d . .
O4 O 0.06003(8) 0.27776(14) -0.13585(11) 0.0209(4) Uani 1 1 d . .
O2 O 0.24283(7) 0.33673(13) 0.12433(11) 0.0179(4) Uani 1 1 d . .
O1 O 0.13425(8) 0.47363(14) 0.33498(11) 0.0214(4) Uani 1 1 d . .
O6 O -0.24052(7) 0.32590(14) -0.20351(11) 0.0206(4) Uani 1 1 d . .
O3 O 0.17450(7) 0.29198(13) -0.02877(11) 0.0181(4) Uani 1 1 d . .
C6 C 0.13077(10) 0.35873(17) 0.08704(15) 0.0134(5) Uani 1 1 d . .
O5 O -0.14886(8) 0.24076(14) -0.27217(11) 0.0197(4) Uani 1 1 d . .
N3 N 0.44827(9) 0.49810(16) 0.39750(13) 0.0204(5) Uani 1 1 d . .
N4 N 0.25897(9) 0.48344(15) 0.42547(13) 0.0177(4) Uani 1 1 d . .
C9 C 0.01249(10) 0.34562(17) -0.02420(15) 0.0139(5) Uani 1 1 d . .
C8 C 0.06466(10) 0.31572(17) -0.05429(15) 0.0149(5) Uani 1 1 d . .
C7 C 0.12700(10) 0.32076(17) 0.00013(15) 0.0141(5) Uani 1 1 d . .
N1 N 0.65404(9) 0.60021(17) 0.34087(14) 0.0212(5) Uani 1 1 d . .
C25 C 0.34263(11) 0.58336(18) 0.38662(16) 0.0198(5) Uani 1 1 d . .
H25 H 0.3565 0.6469 0.3659 0.024 Uiso 1 1 calc R U
C11 C -0.07136(10) 0.29512(18) -0.15211(15) 0.0151(5) Uani 1 1 d . .
H11 H -0.0399 0.2665 -0.1795 0.018 Uiso 1 1 calc R U
C15 C -0.10125(10) 0.38352(17) -0.03136(15) 0.0155(5) Uani 1 1 d . .
H15 H -0.0905 0.4144 0.0246 0.019 Uiso 1 1 calc R U
C10 C -0.05378(10) 0.34159(17) -0.07009(15) 0.0141(5) Uani 1 1 d . .
N2 N 0.46562(9) 0.58327(16) 0.37248(14) 0.0221(5) Uani 1 1 d . .
C1 C 0.07593(10) 0.39105(17) 0.11402(15) 0.0144(5) Uani 1 1 d . .
C4 C 0.19075(10) 0.40518(17) 0.22973(15) 0.0150(5) Uani 1 1 d . .
H4 H 0.2299 0.4096 0.2697 0.018 Uiso 1 1 calc R U
C18 C 0.53019(11) 0.58250(19) 0.36147(15) 0.0185(5) Uani 1 1 d . .
C22 C 0.36163(11) 0.40782(18) 0.43728(15) 0.0186(5) Uani 1 1 d . .
H22 H 0.3888 0.3498 0.4523 0.022 Uiso 1 1 calc R U
C14 C -0.16419(10) 0.38019(17) -0.07450(15) 0.0161(5) Uani 1 1 d . .
H14 H -0.1959 0.4096 -0.0479 0.019 Uiso 1 1 calc R U
C5 C 0.18836(10) 0.36763(17) 0.14777(15) 0.0151(5) Uani 1 1 d . .
C13 C -0.18101(10) 0.33449(17) -0.15575(15) 0.0143(5) Uani 1 1 d . .
C24 C 0.28143(11) 0.57150(18) 0.39765(16) 0.0188(5) Uani 1 1 d . .
H24 H 0.2536 0.6290 0.3848 0.023 Uiso 1 1 calc R U
C21 C 0.38359(11) 0.49928(19) 0.40674(15) 0.0174(5) Uani 1 1 d . .
C2 C 0.07702(11) 0.43065(18) 0.19613(15) 0.0168(5) Uani 1 1 d . .
H2 H 0.0393 0.4530 0.2126 0.020 Uiso 1 1 calc R U
C12 C -0.13385(10) 0.29052(17) -0.19343(15) 0.0146(5) Uani 1 1 d . .
C23 C 0.29931(11) 0.40366(19) 0.44510(16) 0.0188(5) Uani 1 1 d . .
H23 H 0.2841 0.3410 0.4655 0.023 Uiso 1 1 calc R U
C20 C 0.61809(11) 0.6843(2) 0.34353(17) 0.0231(6) Uani 1 1 d . .
H20 H 0.6362 0.7508 0.3385 0.028 Uiso 1 1 calc R U
C17 C 0.56628(11) 0.49412(19) 0.35803(16) 0.0211(5) Uani 1 1 d . .
H17 H 0.5493 0.4268 0.3629 0.025 Uiso 1 1 calc R U
C19 C 0.55617(11) 0.67972(19) 0.35317(17) 0.0220(5) Uani 1 1 d . .
H19 H 0.5321 0.7413 0.3541 0.026 Uiso 1 1 calc R U
C3 C 0.13478(11) 0.43709(17) 0.25420(15) 0.0158(5) Uani 1 1 d . .
C16 C 0.62773(11) 0.5066(2) 0.34730(16) 0.0218(5) Uani 1 1 d . .
H16 H 0.6525 0.4462 0.3443 0.026 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O7 C9 121.82(17)
C8 O4 H4O 110(2)
C5 O2 H2O 107(2)
C3 O1 H1O 112(2)
C13 O6 H6O 112(3)
C1 C6 C5 117.2(2)
C1 C6 C7 119.9(2)
C5 C6 C7 122.9(2)
C12 O5 H5O 111(2)
N2 N3 C21 112.6(2)
C24 N4 C23 117.3(2)
C8 C9 O7 120.0(2)
C8 C9 C10 127.9(2)
O7 C9 C10 112.09(18)
O4 C8 C9 121.3(2)
O4 C8 C7 117.27(19)
C9 C8 C7 121.4(2)
O3 C7 C6 123.2(2)
O3 C7 C8 120.4(2)
C6 C7 C8 116.46(19)
C20 N1 C16 117.6(2)
C24 C25 C21 118.0(2)
C24 C25 H25 121.0
C21 C25 H25 121.0
C12 C11 C10 120.7(2)
C12 C11 H11 119.6
C10 C11 H11 119.6
C14 C15 C10 120.4(2)
C14 C15 H15 119.8
C10 C15 H15 119.8
C11 C10 C15 118.3(2)
C11 C10 C9 121.6(2)
C15 C10 C9 120.1(2)
N3 N2 C18 113.1(2)
O7 C1 C2 117.36(19)
O7 C1 C6 120.3(2)
C2 C1 C6 122.3(2)
C5 C4 C3 119.3(2)
C5 C4 H4 120.4
C3 C4 H4 120.4
C17 C18 C19 119.5(2)
C17 C18 N2 125.3(2)
C19 C18 N2 115.2(2)
C23 C22 C21 118.1(2)
C23 C22 H22 120.9
C21 C22 H22 120.9
C13 C14 C15 120.7(2)
C13 C14 H14 119.6
C15 C14 H14 119.6
O2 C5 C4 119.1(2)
O2 C5 C6 119.2(2)
C4 C5 C6 121.8(2)
O6 C13 C14 126.0(2)
O6 C13 C12 115.2(2)
C14 C13 C12 118.8(2)
N4 C24 C25 123.7(2)
N4 C24 H24 118.1
C25 C24 H24 118.1
C22 C21 C25 119.3(2)
C22 C21 N3 115.7(2)
C25 C21 N3 125.0(2)
C1 C2 C3 118.5(2)
C1 C2 H2 120.7
C3 C2 H2 120.7
O5 C12 C11 118.5(2)
O5 C12 C13 120.6(2)
C11 C12 C13 120.9(2)
N4 C23 C22 123.5(2)
N4 C23 H23 118.2
C22 C23 H23 118.2
N1 C20 C19 123.5(2)
N1 C20 H20 118.2
C19 C20 H20 118.2
C16 C17 C18 118.2(2)
C16 C17 H17 120.9
C18 C17 H17 120.9
C20 C19 C18 118.0(2)
C20 C19 H19 121.0
C18 C19 H19 121.0
O1 C3 C2 117.3(2)
O1 C3 C4 121.8(2)
C2 C3 C4 120.9(2)
N1 C16 C17 123.0(2)
N1 C16 H16 118.5
C17 C16 H16 118.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O7 C1 1.368(3)
O7 C9 1.376(3)
O4 C8 1.356(3)
O4 H4O 0.86(3)
O2 C5 1.363(3)
O2 H2O 0.92(3)
O1 C3 1.356(3)
O1 H1O 0.94(4)
O6 C13 1.359(3)
O6 H6O 0.89(4)
O3 C7 1.260(3)
C6 C1 1.401(3)
C6 C5 1.415(3)
C6 C7 1.437(3)
O5 C12 1.373(3)
O5 H5O 0.87(4)
N3 N2 1.247(3)
N3 C21 1.436(3)
N4 C24 1.340(3)
N4 C23 1.343(3)
C9 C8 1.364(3)
C9 C10 1.472(3)
C8 C7 1.447(3)
N1 C20 1.338(3)
N1 C16 1.345(3)
C25 C24 1.379(3)
C25 C21 1.394(3)
C25 H25 0.9500
C11 C12 1.380(3)
C11 C10 1.402(3)
C11 H11 0.9500
C15 C14 1.396(3)
C15 C10 1.403(3)
C15 H15 0.9500
N2 C18 1.442(3)
C1 C2 1.383(3)
C4 C5 1.366(3)
C4 C3 1.404(3)
C4 H4 0.9500
C18 C17 1.386(3)
C18 C19 1.388(3)
C22 C23 1.380(3)
C22 C21 1.390(3)
C22 H22 0.9500
C14 C13 1.386(3)
C14 H14 0.9500
C13 C12 1.398(3)
C24 H24 0.9500
C2 C3 1.395(3)
C2 H2 0.9500
C23 H23 0.9500
C20 C19 1.380(3)
C20 H20 0.9500
C17 C16 1.383(3)
C17 H17 0.9500
C19 H19 0.9500
C16 H16 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139048299
