#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/74/7157438.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_7157438
loop_
_publ_author_name
'Pretze, Marc'
'Neuber, Christin'
'Kinski, Elisa'
'Belter, Birgit'
'Köckerling, Martin'
'Caflisch, Amedeo'
'Steinbach, Jörg'
'Pietzsch, Jens'
'Mamat, Constantin'
_publ_section_title
;
 Synthesis, radiolabelling and initial biological characterisation of
 ¹⁸F-labelled xanthine derivatives for PET imaging of Eph
 receptors.
;
_journal_issue                   16
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3104
_journal_page_last               3116
_journal_paper_doi               10.1039/d0ob00391c
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C15 H15 Br N4 O3'
_chemical_formula_sum            'C15 H15 Br N4 O3'
_chemical_formula_weight         379.22
_chemical_melting_point_gt       487
_chemical_melting_point_lt       489
_chemical_name_systematic
;
3-(3-(Benzyloxy)propyl)-8-bromo-1H-purine-2,6(3H,7H)-dione 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             january-8-2020
_audit_creation_method           'ciftab-2016 (M. Köckerling, 2016)'
_audit_update_record
;
2020-01-08 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                93.034(1)
_cell_angle_beta                 97.303(1)
_cell_angle_gamma                99.705(1)
_cell_formula_units_Z            2
_cell_length_a                   5.5984(1)
_cell_length_b                   11.0930(2)
_cell_length_c                   12.6395(3)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      38.428
_cell_measurement_theta_min      3.2595
_cell_volume                     765.22(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014-7)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            44798
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         40.568
_diffrn_reflns_theta_min         3.259
_exptl_absorpt_coefficient_mu    2.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_transmission_factor_max   0.74800
_exptl_transmission_factor_min   0.66290
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         9784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0475P)²+0.0510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7701
_reflns_number_total             9784
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00391c2.cif
_cod_data_source_block           MP132-2
_cod_depositor_comments
'Adding full bibliography for 7157438--7157439.cif.'
_cod_database_code               7157438
_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   0.497
_shelx_estimated_absorpt_t_max   0.587
_shelxl_version_number           2014-1
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
C1 C 0.4593(2) -0.43382(7) 0.34393(6) 0.0169(1) Uani 1 1 d . . . . .
C2 C 0.3891(1) -0.25499(7) 0.36693(6) 0.0154(1) Uani 1 1 d . . . . .
C3 C 0.2299(1) -0.32832(7) 0.42145(6) 0.0158(1) Uani 1 1 d . . . . .
C4 C 0.0607(1) -0.28071(7) 0.47906(6) 0.0153(1) Uani 1 1 d . . . . .
C5 C 0.2348(2) -0.07845(7) 0.41830(6) 0.0180(1) Uani 1 1 d . . . . .
C6 C 0.5739(2) -0.05329(8) 0.31104(7) 0.0192(1) Uani 1 1 d . . . . .
H6A H 0.7189 -0.0932 0.3093 0.023 Uiso 1 1 calc R U . . .
H6B H 0.6275 0.0261 0.3541 0.023 Uiso 1 1 calc R U . . .
C7 C 0.4787(2) -0.02890(9) 0.19768(7) 0.0234(2) Uani 1 1 d . . . . .
H7A H 0.3368 0.0135 0.1984 0.028 Uiso 1 1 calc R U . . .
H7B H 0.4241 -0.1076 0.1537 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6802(2) 0.05023(9) 0.14968(7) 0.0264(2) Uani 1 1 d . . . . .
H8A H 0.8261 0.0103 0.1527 0.032 Uiso 1 1 calc R U . . .
H8B H 0.6238 0.0609 0.0739 0.032 Uiso 1 1 calc R U . . .
C9 C 0.9713(2) 0.23301(9) 0.19179(7) 0.0242(2) Uani 1 1 d . . . . .
H9A H 1.0985 0.1823 0.2090 0.029 Uiso 1 1 calc R U . . .
H9B H 1.0126 0.3080 0.2413 0.029 Uiso 1 1 calc R U . . .
C10 C 0.9758(2) 0.26928(8) 0.07851(7) 0.0214(1) Uani 1 1 d . . . . .
C11 C 0.8066(2) 0.3371(1) 0.03336(8) 0.0276(2) Uani 1 1 d . . . . .
H11 H 0.6848 0.3579 0.0734 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8133(2) 0.3746(1) -0.06958(9) 0.0355(2) Uani 1 1 d . . . . .
H12 H 0.6969 0.4208 -0.0996 0.043 Uiso 1 1 calc R U . . .
C13 C 0.9905(2) 0.3443(1) -0.12821(8) 0.0369(3) Uani 1 1 d . . . . .
H13 H 0.9967 0.3705 -0.1983 0.044 Uiso 1 1 calc R U . . .
C14 C 1.1575(2) 0.2764(1) -0.0850(1) 0.0414(3) Uani 1 1 d . . . . .
H14 H 1.2780 0.2552 -0.1256 0.050 Uiso 1 1 calc R U . . .
C15 C 1.1504(2) 0.2384(1) 0.0183(1) 0.0347(2) Uani 1 1 d . . . . .
H15 H 1.2658 0.1912 0.0475 0.042 Uiso 1 1 calc R U . . .
N1 N 0.2784(1) -0.44533(6) 0.40514(5) 0.0166(1) Uani 1 1 d . . . . .
H1 H 0.2063 -0.5129 0.4296 0.020 Uiso 1 1 calc R U . . .
N2 N 0.5347(1) -0.32034(6) 0.31810(5) 0.0176(1) Uani 1 1 d . . . . .
N3 N 0.0776(1) -0.15535(6) 0.47155(6) 0.0179(1) Uani 1 1 d . . . . .
H3 H -0.0245 -0.1203 0.5049 0.022 Uiso 1 1 calc R U . . .
N4 N 0.3928(1) -0.13118(6) 0.36377(6) 0.0174(1) Uani 1 1 d . . . . .
O1 O -0.0888(1) -0.33569(6) 0.53144(5) 0.0204(1) Uani 1 1 d . . . . .
O2 O 0.2322(1) 0.03261(6) 0.42025(6) 0.0254(1) Uani 1 1 d . . . . .
O3 O 0.7404(1) 0.16607(6) 0.20913(6) 0.0238(1) Uani 1 1 d . . . . .
Br1 Br 0.58485(2) -0.57005(2) 0.30036(2) 0.02509(3) 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 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2713 2.4705 '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
N2 C1 N1 114.95(7) . .
N2 C1 Br1 124.48(6) . .
N1 C1 Br1 120.57(6) . .
N2 C2 N4 125.76(7) . .
N2 C2 C3 111.94(7) . .
N4 C2 C3 122.30(7) . .
C2 C3 N1 105.39(6) . .
C2 C3 C4 122.26(7) . .
N1 C3 C4 132.35(7) . .
O1 C4 N3 119.94(7) . .
O1 C4 C3 128.64(7) . .
N3 C4 C3 111.42(6) . .
O2 C5 N4 121.84(7) . .
O2 C5 N3 121.05(8) . .
N4 C5 N3 117.11(7) . .
N4 C6 C7 113.64(7) . .
N4 C6 H6A 108.8 . .
C7 C6 H6A 108.8 . .
N4 C6 H6B 108.8 . .
C7 C6 H6B 108.8 . .
H6A C6 H6B 107.7 . .
C6 C7 C8 109.57(7) . .
C6 C7 H7A 109.8 . .
C8 C7 H7A 109.8 . .
C6 C7 H7B 109.8 . .
C8 C7 H7B 109.8 . .
H7A C7 H7B 108.2 . .
O3 C8 C7 108.44(8) . .
O3 C8 H8A 110.0 . .
C7 C8 H8A 110.0 . .
O3 C8 H8B 110.0 . .
C7 C8 H8B 110.0 . .
H8A C8 H8B 108.4 . .
O3 C9 C10 113.29(8) . .
O3 C9 H9A 108.9 . .
C10 C9 H9A 108.9 . .
O3 C9 H9B 108.9 . .
C10 C9 H9B 108.9 . .
H9A C9 H9B 107.7 . .
C15 C10 C11 118.74(9) . .
C15 C10 C9 121.12(9) . .
C11 C10 C9 120.13(8) . .
C12 C11 C10 120.8(1) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C13 C12 C11 119.7(1) . .
C13 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
C14 C13 C12 120.1(1) . .
C14 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
C13 C14 C15 120.2(1) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C10 C15 C14 120.4(1) . .
C10 C15 H15 119.8 . .
C14 C15 H15 119.8 . .
C1 N1 C3 105.19(6) . .
C1 N1 H1 127.4 . .
C3 N1 H1 127.4 . .
C1 N2 C2 102.54(6) . .
C5 N3 C4 128.20(7) . .
C5 N3 H3 115.9 . .
C4 N3 H3 115.9 . .
C2 N4 C5 118.69(6) . .
C2 N4 C6 121.50(7) . .
C5 N4 C6 119.62(7) . .
C8 O3 C9 112.46(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.330(1) .
C1 N1 1.344(1) .
C1 Br1 1.8572(8) .
C2 N2 1.360(1) .
C2 N4 1.373(1) .
C2 C3 1.379(1) .
C3 N1 1.380(1) .
C3 C4 1.418(1) .
C4 O1 1.2339(9) .
C4 N3 1.387(1) .
C5 O2 1.234(1) .
C5 N4 1.373(1) .
C5 N3 1.383(1) .
C6 N4 1.469(1) .
C6 C7 1.518(1) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.519(1) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 O3 1.420(1) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 O3 1.427(1) .
C9 C10 1.510(1) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C15 1.388(1) .
C10 C11 1.392(1) .
C11 C12 1.390(2) .
C11 H11 0.9500 .
C12 C13 1.385(2) .
C12 H12 0.9500 .
C13 C14 1.375(2) .
C13 H13 0.9500 .
C14 C15 1.396(2) .
C14 H14 0.9500 .
C15 H15 0.9500 .
N1 H1 0.8800 .
N3 H3 0.8800 .
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
C9 H9B Br1 0.99 3.09 3.656(1) 117.5 1_565
N1 H1 O1 0.88 1.81 2.6875(9) 171.0 2_546
N3 H3 O2 0.88 1.94 2.817(1) 175.9 2_556
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
N2 C2 C3 N1 -0.31(9) . . . .
N4 C2 C3 N1 179.25(7) . . . .
N2 C2 C3 C4 179.70(7) . . . .
N4 C2 C3 C4 -0.7(1) . . . .
C2 C3 C4 O1 -179.33(8) . . . .
N1 C3 C4 O1 0.7(2) . . . .
C2 C3 C4 N3 0.6(1) . . . .
N1 C3 C4 N3 -179.39(8) . . . .
N4 C6 C7 C8 -179.02(8) . . . .
C6 C7 C8 O3 -64.2(1) . . . .
O3 C9 C10 C15 -125.4(1) . . . .
O3 C9 C10 C11 56.0(1) . . . .
C15 C10 C11 C12 -0.8(2) . . . .
C9 C10 C11 C12 177.9(1) . . . .
C10 C11 C12 C13 0.0(2) . . . .
C11 C12 C13 C14 0.6(2) . . . .
C12 C13 C14 C15 -0.5(2) . . . .
C11 C10 C15 C14 0.9(2) . . . .
C9 C10 C15 C14 -177.7(1) . . . .
C13 C14 C15 C10 -0.3(2) . . . .
N2 C1 N1 C3 -0.1(1) . . . .
Br1 C1 N1 C3 -179.59(6) . . . .
C2 C3 N1 C1 0.24(9) . . . .
C4 C3 N1 C1 -179.78(9) . . . .
N1 C1 N2 C2 -0.09(9) . . . .
Br1 C1 N2 C2 179.38(6) . . . .
N4 C2 N2 C1 -179.30(8) . . . .
C3 C2 N2 C1 0.25(9) . . . .
O2 C5 N3 C4 -178.58(8) . . . .
N4 C5 N3 C4 1.3(1) . . . .
O1 C4 N3 C5 179.01(8) . . . .
C3 C4 N3 C5 -0.9(1) . . . .
N2 C2 N4 C5 -179.45(8) . . . .
C3 C2 N4 C5 1.0(1) . . . .
N2 C2 N4 C6 -4.4(1) . . . .
C3 C2 N4 C6 176.08(7) . . . .
O2 C5 N4 C2 178.63(8) . . . .
N3 C5 N4 C2 -1.2(1) . . . .
O2 C5 N4 C6 3.5(1) . . . .
N3 C5 N4 C6 -176.37(7) . . . .
C7 C6 N4 C2 97.4(1) . . . .
C7 C6 N4 C5 -87.6(1) . . . .
C7 C8 O3 C9 162.63(8) . . . .
C10 C9 O3 C8 65.2(1) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353349
