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#$Date: 2022-05-12 11:04:27 +0300 (Thu, 12 May 2022) $
#$Revision: 275361 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105231.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_8105231
loop_
_publ_author_name
'Li, Peizhe'
'Liu, Lei'
'Lou, Benyong'
'Zhan, Hongbing'
_publ_section_title
;
 Crystal structure of
 3,7-dimethyl-1-(5-oxohexyl)-3,7-dihydro-1H-purine-2,6-dione
 4-hydroxybenzoic acid, C20H24N4O6
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              599
_journal_page_last               600
_journal_paper_doi               10.1515/ncrs-2019-0841
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C13 H18 N4 O3, C7 H6 O3 '
_chemical_formula_sum            'C20 H24 N4 O6'
_chemical_formula_weight         416.43
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                64.328(6)
_cell_angle_beta                 70.778(6)
_cell_angle_gamma                86.678(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2441(5)
_cell_length_b                   11.6409(6)
_cell_length_c                   12.0107(9)
_cell_measurement_reflns_used    3126
_cell_measurement_temperature    100(10)
_cell_measurement_theta_max      29.2150
_cell_measurement_theta_min      2.6300
_cell_volume                     976.09(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(10)
_diffrn_detector_area_resol_mean 5.2684
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8047
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.446
_diffrn_reflns_theta_min         1.951
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.90440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0671
_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)+(0.0591P)²+1.1819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1702
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3586
_reflns_number_total             4538
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0841_suppl.cif
_cod_data_source_block           lou
_cod_original_cell_volume        976.09(12)
_cod_database_code               8105231
_shelx_shelxl_version_number     2018/3
_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
O1 O 1.1373(3) 1.4219(2) -0.58966(19) 0.0361(5) Uani 1 1 d . . . . .
O2 O 0.6617(2) 0.86534(18) -0.45472(17) 0.0262(4) Uani 1 1 d . . . . .
O3 O 0.6666(2) 0.89051(17) -0.08677(17) 0.0210(4) Uani 1 1 d . . . . .
O4 O 0.6466(2) 0.88597(17) 0.14372(18) 0.0225(4) Uani 1 1 d . . . . .
O5 O 1.0450(2) 1.31397(18) 0.17545(19) 0.0277(4) Uani 1 1 d . . . . .
O6 O 1.1294(2) 1.38124(18) -0.04199(18) 0.0247(4) Uani 1 1 d . . . . .
N1 N 0.6662(2) 0.87322(19) -0.26895(19) 0.0170(4) Uani 1 1 d . . . . .
N2 N 0.4885(3) 0.7130(2) -0.2588(2) 0.0195(5) Uani 1 1 d . . . . .
N3 N 0.3165(2) 0.56413(19) -0.0393(2) 0.0179(4) Uani 1 1 d . . . . .
N4 N 0.4017(2) 0.64925(19) 0.06879(19) 0.0174(4) Uani 1 1 d . . . . .
C1 C 1.2065(4) 1.3783(3) -0.3995(3) 0.0323(7) Uani 1 1 d . . . . .
H1A H 1.308141 1.439458 -0.461065 0.048 Uiso 1 1 calc R U . . .
H1B H 1.243194 1.298254 -0.344670 0.048 Uiso 1 1 calc R U . . .
H1C H 1.130102 1.414469 -0.343534 0.048 Uiso 1 1 calc R U . . .
C2 C 1.1115(3) 1.3520(2) -0.4749(3) 0.0234(6) Uani 1 1 d . . . . .
C3 C 0.9812(3) 1.2359(2) -0.3988(2) 0.0225(5) Uani 1 1 d . . . . .
H3A H 0.904541 1.239100 -0.317352 0.027 Uiso 1 1 calc R U . . .
H3B H 1.043225 1.158389 -0.372915 0.027 Uiso 1 1 calc R U . . .
C4 C 0.8704(3) 1.2229(2) -0.4726(3) 0.0241(6) Uani 1 1 d . . . . .
H4A H 0.945919 1.212248 -0.550138 0.029 Uiso 1 1 calc R U . . .
H4B H 0.815541 1.303161 -0.504745 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7295(3) 1.1106(2) -0.3903(2) 0.0218(5) Uani 1 1 d . . . . .
H5A H 0.657092 1.118669 -0.310419 0.026 Uiso 1 1 calc R U . . .
H5B H 0.654618 1.114734 -0.441360 0.026 Uiso 1 1 calc R U . . .
C6 C 0.8018(3) 0.9815(2) -0.3501(2) 0.0200(5) Uani 1 1 d . . . . .
H6A H 0.872604 0.972813 -0.429972 0.024 Uiso 1 1 calc R U . . .
H6B H 0.878239 0.977906 -0.300299 0.024 Uiso 1 1 calc R U . . .
C7 C 0.6101(3) 0.8323(2) -0.1333(2) 0.0164(5) Uani 1 1 d . . . . .
C8 C 0.6080(3) 0.8201(2) -0.3352(2) 0.0189(5) Uani 1 1 d . . . . .
C9 C 0.4130(4) 0.6566(3) -0.3208(3) 0.0257(6) Uani 1 1 d . . . . .
H9A H 0.438476 0.567172 -0.294625 0.038 Uiso 1 1 calc R U . . .
H9B H 0.462409 0.704772 -0.416428 0.038 Uiso 1 1 calc R U . . .
H9C H 0.287679 0.660014 -0.292720 0.038 Uiso 1 1 calc R U . . .
C10 C 0.4318(3) 0.6666(2) -0.1250(2) 0.0171(5) Uani 1 1 d . . . . .
C11 C 0.4890(3) 0.7223(2) -0.0638(2) 0.0163(5) Uani 1 1 d . . . . .
C12 C 0.4164(3) 0.6694(2) 0.1767(2) 0.0216(5) Uani 1 1 d . . . . .
H12A H 0.339001 0.604583 0.260097 0.032 Uiso 1 1 calc R U . . .
H12B H 0.384479 0.754923 0.166495 0.032 Uiso 1 1 calc R U . . .
H12C H 0.535715 0.662320 0.176097 0.032 Uiso 1 1 calc R U . . .
C13 C 0.3019(3) 0.5569(2) 0.0776(2) 0.0191(5) Uani 1 1 d . . . . .
H13 H 0.228429 0.492999 0.158459 0.023 Uiso 1 1 calc R U . . .
C14 C 0.7384(3) 0.9901(2) 0.1235(2) 0.0170(5) Uani 1 1 d . . . . .
C15 C 0.7373(3) 1.0035(2) 0.2335(2) 0.0182(5) Uani 1 1 d . . . . .
H15 H 0.670130 0.942674 0.318918 0.022 Uiso 1 1 calc R U . . .
C16 C 0.8342(3) 1.1055(2) 0.2178(2) 0.0182(5) Uani 1 1 d . . . . .
H16 H 0.833832 1.114261 0.292938 0.022 Uiso 1 1 calc R U . . .
C17 C 0.8342(3) 1.0812(2) -0.0021(2) 0.0185(5) Uani 1 1 d . . . . .
H17 H 0.833066 1.073480 -0.077392 0.022 Uiso 1 1 calc R U . . .
C18 C 0.9304(3) 1.1825(2) -0.0159(2) 0.0188(5) Uani 1 1 d . . . . .
H18 H 0.996326 1.244164 -0.101266 0.023 Uiso 1 1 calc R U . . .
C19 C 0.9326(3) 1.1959(2) 0.0931(2) 0.0176(5) Uani 1 1 d . . . . .
C20 C 1.0394(3) 1.3018(2) 0.0802(2) 0.0200(5) Uani 1 1 d . . . . .
H4 H 0.651(5) 0.885(4) 0.065(4) 0.064(12) Uiso 1 1 d . . . . .
H6 H 1.191(4) 1.445(3) -0.042(3) 0.044(10) Uiso 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C14 O4 H4 112(3) . .
C20 O6 H6 109(2) . .
C7 N1 C8 126.4(2) . .
C7 N1 C6 116.9(2) . .
C8 N1 C6 116.75(19) . .
C10 N2 C8 119.3(2) . .
C10 N2 C9 120.2(2) . .
C8 N2 C9 120.3(2) . .
C13 N3 C10 103.9(2) . .
C13 N4 C11 106.4(2) . .
C13 N4 C12 127.0(2) . .
C11 N4 C12 126.6(2) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O1 C2 C1 121.4(2) . .
O1 C2 C3 122.3(2) . .
C1 C2 C3 116.3(2) . .
C2 C3 C4 114.7(2) . .
C2 C3 H3A 108.6 . .
C4 C3 H3A 108.6 . .
C2 C3 H3B 108.6 . .
C4 C3 H3B 108.6 . .
H3A C3 H3B 107.6 . .
C3 C4 C5 113.9(2) . .
C3 C4 H4A 108.8 . .
C5 C4 H4A 108.8 . .
C3 C4 H4B 108.8 . .
C5 C4 H4B 108.8 . .
H4A C4 H4B 107.7 . .
C6 C5 C4 112.8(2) . .
C6 C5 H5A 109.0 . .
C4 C5 H5A 109.0 . .
C6 C5 H5B 109.0 . .
C4 C5 H5B 109.0 . .
H5A C5 H5B 107.8 . .
N1 C6 C5 112.84(19) . .
N1 C6 H6A 109.0 . .
C5 C6 H6A 109.0 . .
N1 C6 H6B 109.0 . .
C5 C6 H6B 109.0 . .
H6A C6 H6B 107.8 . .
O3 C7 N1 120.3(2) . .
O3 C7 C11 127.3(2) . .
N1 C7 C11 112.4(2) . .
O2 C8 N2 121.7(2) . .
O2 C8 N1 121.3(2) . .
N2 C8 N1 117.0(2) . .
N2 C9 H9A 109.5 . .
N2 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N2 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N3 C10 C11 112.2(2) . .
N3 C10 N2 125.7(2) . .
C11 C10 N2 122.1(2) . .
C10 C11 N4 104.7(2) . .
C10 C11 C7 122.7(2) . .
N4 C11 C7 132.6(2) . .
N4 C12 H12A 109.5 . .
N4 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N4 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N3 C13 N4 112.8(2) . .
N3 C13 H13 123.6 . .
N4 C13 H13 123.6 . .
O4 C14 C15 117.7(2) . .
O4 C14 C17 122.3(2) . .
C15 C14 C17 120.1(2) . .
C16 C15 C14 119.7(2) . .
C16 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
C15 C16 C19 120.8(2) . .
C15 C16 H16 119.6 . .
C19 C16 H16 119.6 . .
C18 C17 C14 119.4(2) . .
C18 C17 H17 120.3 . .
C14 C17 H17 120.3 . .
C17 C18 C19 121.0(2) . .
C17 C18 H18 119.5 . .
C19 C18 H18 119.5 . .
C18 C19 C16 119.0(2) . .
C18 C19 C20 121.7(2) . .
C16 C19 C20 119.3(2) . .
O5 C20 O6 122.9(2) . .
O5 C20 C19 122.6(2) . .
O6 C20 C19 114.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.210(3) .
O2 C8 1.219(3) .
O3 C7 1.235(3) .
O4 C14 1.353(3) .
O4 H4 0.94(4) .
O5 C20 1.227(3) .
O6 C20 1.322(3) .
O6 H6 0.92(4) .
N1 C7 1.397(3) .
N1 C8 1.399(3) .
N1 C6 1.473(3) .
N2 C10 1.369(3) .
N2 C8 1.387(3) .
N2 C9 1.466(3) .
N3 C13 1.334(3) .
N3 C10 1.345(3) .
N4 C13 1.338(3) .
N4 C11 1.385(3) .
N4 C12 1.456(3) .
C1 C2 1.504(4) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.506(3) .
C3 C4 1.519(4) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.528(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.518(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C11 1.417(3) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C11 1.365(3) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13 0.9500 .
C14 C15 1.393(3) .
C14 C17 1.397(3) .
C15 C16 1.378(3) .
C15 H15 0.9500 .
C16 C19 1.394(3) .
C16 H16 0.9500 .
C17 C18 1.378(4) .
C17 H17 0.9500 .
C18 C19 1.389(3) .
C18 H18 0.9500 .
C19 C20 1.480(4) .
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
_geom_hbond_publ_flag
O4 H4 O3 0.94(4) 1.75(4) 2.696(3) 177(4) . yes
C17 H17 O3 0.95 2.66 3.333(3) 128.2 . yes
O6 H6 N3 0.92(4) 1.80(4) 2.718(3) 177(3) 1_665 yes
C13 H13 O5 0.95 2.54 3.168(3) 123.6 1_445 yes
C15 H15 O2 0.95 2.44 3.218(3) 138.7 1_556 yes
C13 H13 O1 0.95 2.61 3.394(3) 140.2 1_446 yes
C12 H12A O1 0.98 2.38 3.314(3) 159.7 1_446 yes
