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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/68/7216893.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_7216893
loop_
_publ_author_name
'Al-Azmi, Amal'
'Booth, Brian L.'
'Carpenter, Robert A.'
'Carvalho, Alice'
'Marrelec, Elodie'
'Pritchard, Robin G.'
'ProenÃ§a, M. Fernanda J. R. P.'
_publ_section_title
;
 Facile synthesis of 6-cyano-9-substituted-9H-purines and their ring
 expansion to 8-(arylamino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidines
;
_journal_issue                   20
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2532
_journal_paper_doi               10.1039/b106539b
_journal_year                    2001
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H14 N6 O1'
_chemical_formula_structural     'C14 H14 N6 O1'
_chemical_formula_sum            'C14 H14 N6 O'
_chemical_formula_weight         282.31
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2001-07-02T08:30:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.542(9)
_cell_length_b                   12.114(2)
_cell_length_c                   7.3571(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.1
_cell_measurement_theta_min      16.4
_cell_measurement_wavelength     1.54178
_cell_volume                     2722.0(10)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1181
_diffrn_reflns_av_unetI/netI     0.1359
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4659
_diffrn_reflns_theta_full        65.17
_diffrn_reflns_theta_max         65.17
_diffrn_reflns_theta_min         4.66
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.7751
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1572
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0665P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1703
_reflns_number_gt                1019
_reflns_number_total             2317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b106539b.txt
_cod_data_source_block           t
_cod_depositor_comments
;

2018-03-13
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2722.1(10)
_cod_original_formula_sum        'C28 H28 N12 O2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     564.62
_cod_database_code               7216893
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -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
C2 C 0.47613(12) 0.4880(3) 0.2996(6) 0.0497(10) Uani 1 1 d .
C4 C 0.46891(12) 0.6653(3) 0.1515(5) 0.0463(9) Uani 1 1 d .
C4A C 0.51541(11) 0.6526(3) 0.1121(5) 0.0467(9) Uani 1 1 d .
C6 C 0.57746(13) 0.7184(3) -0.0112(7) 0.0577(12) Uani 1 1 d .
C8 C 0.58238(12) 0.5527(3) 0.1341(6) 0.0483(9) Uani 1 1 d .
C8A C 0.53729(11) 0.5600(3) 0.1735(5) 0.0450(10) Uani 1 1 d .
C9 C 0.40376(13) 0.5775(4) 0.2903(8) 0.0581(12) Uani 1 1 d .
C12 C 0.64980(11) 0.4355(3) 0.1879(6) 0.0525(10) Uani 1 1 d .
C13 C 0.68184(14) 0.4965(4) 0.0999(7) 0.0709(14) Uani 1 1 d .
C14 C 0.72501(14) 0.4626(4) 0.1043(8) 0.0746(14) Uani 1 1 d .
C15 C 0.73705(13) 0.3658(4) 0.1915(7) 0.0699(13) Uani 1 1 d .
C16 C 0.70491(15) 0.3056(5) 0.2778(8) 0.0728(14) Uani 1 1 d .
C17 C 0.66220(13) 0.3387(3) 0.2768(7) 0.0606(12) Uani 1 1 d .
C19 C 0.81067(17) 0.3730(6) 0.1013(11) 0.140(3) Uani 1 1 d .
H19A H 0.8015 0.3788 -0.0231 0.211 Uiso 1 1 calc R
H19B H 0.8368 0.329 0.1082 0.211 Uiso 1 1 calc R
H19C H 0.8165 0.4453 0.1486 0.211 Uiso 1 1 calc R
O18 O 0.77843(10) 0.3245(4) 0.2008(6) 0.1095(14) Uani 1 1 d .
N1 N 0.51698(10) 0.4754(2) 0.2686(4) 0.0510(8) Uani 1 1 d .
N3 N 0.45046(9) 0.5744(2) 0.2442(4) 0.0489(8) Uani 1 1 d .
N5 N 0.53564(10) 0.7354(3) 0.0176(5) 0.0533(9) Uani 1 1 d .
N7 N 0.60325(10) 0.6328(3) 0.0425(5) 0.0561(9) Uani 1 1 d .
N10 N 0.44397(10) 0.7466(3) 0.1095(5) 0.0575(9) Uani 1 1 d .
N11 N 0.60486(10) 0.4632(3) 0.1944(5) 0.0539(9) Uani 1 1 d .
H2 H 0.4572(15) 0.432(4) 0.354(7) 0.092(16) Uiso 1 1 d .
H6 H 0.5915(13) 0.784(3) -0.076(6) 0.071(13) Uiso 1 1 d .
H9A H 0.3848(16) 0.574(5) 0.175(8) 0.109(18) Uiso 1 1 d .
H9B H 0.3945(15) 0.508(4) 0.357(6) 0.091(15) Uiso 1 1 d .
H9C H 0.3948(16) 0.640(5) 0.364(8) 0.12(2) Uiso 1 1 d .
H10 H 0.4653(13) 0.795(3) 0.049(6) 0.065(13) Uiso 1 1 d .
H11 H 0.5892(11) 0.422(3) 0.246(5) 0.043(12) Uiso 1 1 d .
H13 H 0.6725(15) 0.563(5) 0.047(7) 0.099(19) Uiso 1 1 d .
H14 H 0.749(2) 0.504(5) 0.036(8) 0.13(2) Uiso 1 1 d .
H16 H 0.7141(18) 0.242(5) 0.335(9) 0.13(2) Uiso 1 1 d .
H17 H 0.6359(11) 0.298(3) 0.338(5) 0.054(11) 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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 C2 N3 126.7(4)
N10 C4 N3 118.6(3)
N10 C4 C4A 127.7(4)
N3 C4 C4A 113.7(3)
N5 C4A C8A 122.9(3)
N5 C4A C4 117.7(3)
C8A C4A C4 119.4(3)
N5 C6 N7 129.5(4)
N7 C8 N11 120.1(3)
N7 C8 C8A 121.4(4)
N11 C8 C8A 118.5(4)
C4A C8A N1 123.3(3)
C4A C8A C8 117.1(3)
N1 C8A C8 119.6(3)
C13 C12 C17 118.3(4)
C13 C12 N11 125.1(4)
C17 C12 N11 116.6(4)
C14 C13 C12 120.3(5)
C13 C14 C15 121.0(5)
O18 C15 C16 116.4(5)
O18 C15 C14 125.5(4)
C16 C15 C14 118.2(4)
C17 C16 C15 121.5(5)
C16 C17 C12 120.6(4)
C19 O18 C15 119.1(5)
C2 N1 C8A 116.0(3)
C2 N3 C4 120.8(3)
C2 N3 C9 120.5(3)
C4 N3 C9 118.6(3)
C6 N5 C4A 114.0(3)
C8 N7 C6 115.0(3)
C8 N11 C12 132.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 N1 1.277(5)
C2 N3 1.370(5)
C4 N10 1.283(4)
C4 N3 1.413(5)
C4 C4A 1.458(5)
C4A N5 1.367(5)
C4A C8A 1.382(5)
C6 N5 1.311(5)
C6 N7 1.361(5)
C8 N7 1.343(5)
C8 N11 1.357(5)
C8 C8A 1.410(5)
C8A N1 1.388(5)
C9 N3 1.466(5)
C12 C13 1.386(6)
C12 C17 1.396(6)
C12 N11 1.414(5)
C13 C14 1.381(6)
C14 C15 1.387(6)
C15 O18 1.361(5)
C15 C16 1.378(7)
C16 C17 1.365(6)
C19 O18 1.360(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11022357
