#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/36/7023644.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_7023644
loop_
_publ_author_name
'Sinha, Indranil'
'Kösters, Jutta'
'Hepp, Alexander'
'Müller, Jens'
_publ_section_title
;
 6-Substituted purines containing thienyl or furyl substituents as
 artificial nucleobases for metal-mediated base pairing.
;
_journal_issue                   45
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16080
_journal_page_last               16089
_journal_paper_doi               10.1039/c3dt51691a
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C10 H8 N4 O'
_chemical_formula_weight         200.20
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.245(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4259(2)
_cell_length_b                   17.6396(5)
_cell_length_c                   6.8688(2)
_cell_measurement_reflns_used    5173
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.0314
_cell_measurement_theta_min      2.3092
_cell_volume                     890.44(4)
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc.)'
_computing_data_collection       'APEX2 v2012.2-0'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc.)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEX-II CCD-detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_radiation_source         Microfocus
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15422
_diffrn_reflns_theta_full        30.08
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0623P)²+0.3594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                2226
_reflns_number_total             2620
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt51691a.txt
_cod_data_source_block           sad
_cod_database_code               7023644
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.19315(14) 0.68724(6) 0.38994(16) 0.0156(2) Uani 1 1 d .
N1 N 0.04694(13) 0.73008(5) 0.32191(15) 0.0184(2) Uani 1 1 d .
C2 C 0.06367(16) 0.80580(6) 0.33410(18) 0.0200(2) Uani 1 1 d .
H2 H -0.0431 0.8338 0.2874 0.024 Uiso 1 1 calc R
N2 N 0.20935(13) 0.84716(5) 0.40260(15) 0.0189(2) Uani 1 1 d .
C3 C 0.35093(14) 0.80321(6) 0.46796(16) 0.0158(2) Uani 1 1 d .
N3 N 0.52209(13) 0.82570(5) 0.54694(14) 0.0183(2) Uani 1 1 d .
C31 C 0.58696(18) 0.90315(7) 0.5746(2) 0.0271(3) Uani 1 1 d .
H31A H 0.7058 0.9033 0.6578 0.041 Uiso 1 1 calc R
H33A H 0.5001 0.9328 0.6381 0.041 Uiso 1 1 calc R
H32A H 0.5988 0.9256 0.4465 0.041 Uiso 1 1 calc R
C4 C 0.61918(16) 0.76066(7) 0.59052(18) 0.0206(2) Uani 1 1 d .
H4 H 0.7437 0.7608 0.6471 0.025 Uiso 1 1 calc R
N4 N 0.52665(13) 0.69764(6) 0.54792(15) 0.0197(2) Uani 1 1 d .
C5 C 0.35467(14) 0.72361(6) 0.46915(16) 0.0155(2) Uani 1 1 d .
C6 C 0.17896(14) 0.60550(6) 0.37448(16) 0.0167(2) Uani 1 1 d .
C7 C 0.29228(16) 0.54903(6) 0.44986(19) 0.0216(2) Uani 1 1 d .
H7 H 0.4049 0.5548 0.5336 0.026 Uiso 1 1 calc R
C8 C 0.20973(17) 0.47948(7) 0.37928(19) 0.0233(3) Uani 1 1 d .
H8 H 0.2561 0.4298 0.4060 0.028 Uiso 1 1 calc R
C9 C 0.05194(17) 0.49868(6) 0.26642(18) 0.0224(2) Uani 1 1 d .
H9 H -0.0317 0.4634 0.1994 0.027 Uiso 1 1 calc R
O1 O 0.02883(11) 0.57553(5) 0.26151(12) 0.0202(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 0.0033 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
N1 C1 C5 118.67(10)
N1 C1 C6 119.04(10)
C5 C1 C6 122.27(10)
C2 N1 C1 118.20(10)
N2 C2 N1 129.00(10)
N2 C2 H2 115.5
N1 C2 H2 115.5
C3 N2 C2 111.22(10)
N2 C3 N3 127.52(10)
N2 C3 C5 126.74(10)
N3 C3 C5 105.74(9)
C4 N3 C3 105.95(9)
C4 N3 C31 127.39(10)
C3 N3 C31 126.65(10)
N3 C31 H31A 109.5
N3 C31 H33A 109.5
H31A C31 H33A 109.5
N3 C31 H32A 109.5
H31A C31 H32A 109.5
H33A C31 H32A 109.5
N4 C4 N3 114.72(10)
N4 C4 H4 122.6
N3 C4 H4 122.6
C4 N4 C5 103.24(9)
N4 C5 C1 133.47(10)
N4 C5 C3 110.35(9)
C1 C5 C3 116.16(9)
C7 C6 O1 110.02(10)
C7 C6 C1 131.90(10)
O1 C6 C1 118.06(9)
C6 C7 C8 106.80(11)
C6 C7 H7 126.6
C8 C7 H7 126.6
C9 C8 C7 105.93(10)
C9 C8 H8 127.0
C7 C8 H8 127.0
C8 C9 O1 110.99(10)
C8 C9 H9 124.5
O1 C9 H9 124.5
C9 O1 C6 106.25(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3500(13)
C1 C5 1.3997(15)
C1 C6 1.4486(15)
N1 C2 1.3429(14)
C2 N2 1.3334(15)
C2 H2 0.9500
N2 C3 1.3313(14)
C3 N3 1.3673(14)
C3 C5 1.4044(14)
N3 C4 1.3652(15)
N3 C31 1.4521(15)
C31 H31A 0.9800
C31 H33A 0.9800
C31 H32A 0.9800
C4 N4 1.3176(15)
C4 H4 0.9500
N4 C5 1.3912(14)
C6 C7 1.3578(15)
C6 O1 1.3699(13)
C7 C8 1.4250(16)
C7 H7 0.9500
C8 C9 1.3521(17)
C8 H8 0.9500
C9 O1 1.3661(13)
C9 H9 0.9500
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
C5 C1 N1 C2 -0.16(15)
C6 C1 N1 C2 -178.77(10)
C1 N1 C2 N2 1.41(19)
N1 C2 N2 C3 -1.20(18)
C2 N2 C3 N3 179.61(11)
C2 N2 C3 C5 -0.20(16)
N2 C3 N3 C4 -179.64(11)
C5 C3 N3 C4 0.20(12)
N2 C3 N3 C31 -0.72(19)
C5 C3 N3 C31 179.12(11)
C3 N3 C4 N4 -0.28(14)
C31 N3 C4 N4 -179.19(12)
N3 C4 N4 C5 0.23(14)
C4 N4 C5 C1 178.11(12)
C4 N4 C5 C3 -0.08(12)
N1 C1 C5 N4 -179.09(11)
C6 C1 C5 N4 -0.53(19)
N1 C1 C5 C3 -0.98(15)
C6 C1 C5 C3 177.58(10)
N2 C3 C5 N4 179.76(11)
N3 C3 C5 N4 -0.08(12)
N2 C3 C5 C1 1.22(16)
N3 C3 C5 C1 -178.62(9)
N1 C1 C6 C7 -170.67(12)
C5 C1 C6 C7 10.77(19)
N1 C1 C6 O1 11.07(15)
C5 C1 C6 O1 -167.48(10)
O1 C6 C7 C8 0.46(13)
C1 C6 C7 C8 -177.90(12)
C6 C7 C8 C9 -0.14(14)
C7 C8 C9 O1 -0.24(14)
C8 C9 O1 C6 0.52(13)
C7 C6 O1 C9 -0.61(13)
C1 C6 O1 C9 178.01(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 482729
