#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/54/7235464.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_7235464
loop_
_publ_author_name
'Radhakrishnan, K.'
'Sharma, Namita'
'Kundu, Lal Mohan'
_publ_section_title
;
 Direct synthesis of 5- and 6-substituted 2-aminopyrimidines as potential
 non-natural nucleobase analogues
;
_journal_issue                   29
_journal_name_full               'RSC Adv.'
_journal_page_first              15087
_journal_paper_doi               10.1039/C4RA00249K
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         '2(C8 H13 N3 O), H2 O'
_chemical_formula_sum            'C16 H28 N6 O3'
_chemical_formula_weight         352.44
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/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                 103.855(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.3425(7)
_cell_length_b                   13.9961(7)
_cell_length_c                   14.4876(6)
_cell_measurement_temperature    296(2)
_cell_volume                     3808.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17056
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.552
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+6.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                2518
_reflns_number_total             3352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra00249k2.cif
_cod_data_source_block           5-methyl-6-isopropylisocytosine_tautomer
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7235464
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C4 C 0.3221(2) 0.3843(3) 0.6770(3) 0.0441(12) Uani 1 1 d .
C1 C 0.3116(2) 0.2243(3) 0.6441(3) 0.0430(12) Uani 1 1 d .
C5 C 0.3952(3) 0.4519(3) 0.8332(3) 0.0586(14) Uani 1 1 d .
H5 H 0.3853 0.5111 0.7962 0.070 Uiso 1 1 calc R
C2 C 0.3808(2) 0.2749(3) 0.7970(3) 0.0470(12) Uani 1 1 d .
C3 C 0.3654(2) 0.3708(3) 0.7662(3) 0.0444(12) Uani 1 1 d .
C7 C 0.3579(3) 0.4604(4) 0.9138(4) 0.0770(17) Uani 1 1 d .
H7A H 0.3077 0.4688 0.8880 0.116 Uiso 1 1 calc R
H7B H 0.3765 0.5145 0.9526 0.116 Uiso 1 1 calc R
H7C H 0.3660 0.4034 0.9516 0.116 Uiso 1 1 calc R
C6 C 0.4760(3) 0.4471(5) 0.8723(4) 0.103(2) Uani 1 1 d .
H6A H 0.4873 0.3984 0.9203 0.154 Uiso 1 1 calc R
H6B H 0.4931 0.5077 0.8995 0.154 Uiso 1 1 calc R
H6C H 0.4984 0.4321 0.8216 0.154 Uiso 1 1 calc R
C12 C 0.3891(2) 0.8246(3) 0.8567(4) 0.0502(12) Uani 1 1 d .
C10 C 0.3788(2) 0.9427(3) 0.7341(4) 0.0529(13) Uani 1 1 d .
C11 C 0.3781(2) 0.8427(3) 0.7627(3) 0.0496(12) Uani 1 1 d .
C9 C 0.3940(2) 0.9904(3) 0.8909(3) 0.0480(12) Uani 1 1 d .
C13 C 0.3646(3) 0.7642(4) 0.6888(4) 0.0706(16) Uani 1 1 d .
H13 H 0.3668 0.7060 0.7270 0.085 Uiso 1 1 calc R
C15 C 0.4220(3) 0.7498(5) 0.6383(4) 0.095(2) Uani 1 1 d .
H15A H 0.4339 0.8099 0.6142 0.142 Uiso 1 1 calc R
H15B H 0.4060 0.7061 0.5865 0.142 Uiso 1 1 calc R
H15C H 0.4633 0.7240 0.6816 0.142 Uiso 1 1 calc R
C14 C 0.2921(4) 0.7626(5) 0.6289(5) 0.126(3) Uani 1 1 d .
H14A H 0.2835 0.8200 0.5917 0.189 Uiso 1 1 calc R
H14B H 0.2588 0.7585 0.6683 0.189 Uiso 1 1 calc R
H14C H 0.2865 0.7082 0.5874 0.189 Uiso 1 1 calc R
N5 N 0.35178(19) 0.2051(3) 0.7325(2) 0.0475(10) Uani 1 1 d .
H5A H 0.3596 0.1464 0.7490 0.057 Uiso 1 1 calc R
N2 N 0.3851(2) 1.0137(3) 0.8006(3) 0.0544(11) Uani 1 1 d .
N4 N 0.29488(18) 0.3121(3) 0.6149(2) 0.0459(10) Uani 1 1 d .
N1 N 0.39840(19) 0.8989(3) 0.9204(2) 0.0501(10) Uani 1 1 d .
H1 H 0.4072 0.8867 0.9803 0.060 Uiso 1 1 calc R
N6 N 0.2876(2) 0.1492(3) 0.5880(3) 0.0558(12) Uani 1 1 d .
N3 N 0.3984(3) 1.0589(4) 0.9561(4) 0.0655(14) Uani 1 1 d .
O1 O 0.41676(18) 0.2486(2) 0.8771(2) 0.0620(10) Uani 1 1 d .
O2 O 0.3733(2) 0.9677(2) 0.6496(2) 0.0751(11) Uani 1 1 d .
C8 C 0.2992(3) 0.4820(3) 0.6383(3) 0.0660(15) Uani 1 1 d .
H8A H 0.2754 0.5143 0.6803 0.099 Uiso 1 1 calc R
H8B H 0.2674 0.4760 0.5766 0.099 Uiso 1 1 calc R
H8C H 0.3404 0.5182 0.6332 0.099 Uiso 1 1 calc R
C16 C 0.3934(3) 0.7279(3) 0.9033(4) 0.0692(15) Uani 1 1 d .
H16A H 0.3479 0.6970 0.8852 0.104 Uiso 1 1 calc R
H16B H 0.4068 0.7353 0.9711 0.104 Uiso 1 1 calc R
H16C H 0.4284 0.6896 0.8832 0.104 Uiso 1 1 calc R
O3 O 0.5429(2) 0.1409(4) 0.8868(3) 0.0837(12) Uani 1 1 d D
H3A H 0.398(2) 1.049(3) 1.015(4) 0.068(17) Uiso 1 1 d .
H3B H 0.398(3) 1.119(4) 0.939(4) 0.072(18) Uiso 1 1 d .
H6M H 0.263(2) 0.159(3) 0.528(4) 0.060(16) Uiso 1 1 d .
H6N H 0.306(2) 0.092(4) 0.602(3) 0.052(15) Uiso 1 1 d .
H3M H 0.498(2) 0.168(5) 0.878(5) 0.16(3) Uiso 1 1 d D
H3N H 0.539(5) 0.082(3) 0.856(5) 0.17(4) Uiso 1 1 d 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
N4 C4 C3 124.5(4)
N4 C4 C8 113.1(4)
C3 C4 C8 122.3(4)
N4 C1 N6 121.0(4)
N4 C1 N5 122.0(4)
N6 C1 N5 117.0(4)
C3 C5 C7 112.0(4)
C3 C5 C6 113.6(4)
C7 C5 C6 110.5(4)
O1 C2 N5 117.7(4)
O1 C2 C3 126.4(4)
N5 C2 C3 115.8(4)
C4 C3 C2 117.4(4)
C4 C3 C5 123.4(4)
C2 C3 C5 119.1(4)
C11 C12 N1 119.9(4)
C11 C12 C16 126.8(4)
N1 C12 C16 113.3(4)
O2 C10 N2 117.2(4)
O2 C10 C11 122.7(4)
N2 C10 C11 120.1(4)
C12 C11 C10 117.1(4)
C12 C11 C13 122.4(4)
C10 C11 C13 120.5(4)
N2 C9 N3 119.8(5)
N2 C9 N1 122.1(4)
N3 C9 N1 118.1(4)
C14 C13 C15 115.5(5)
C14 C13 C11 114.2(5)
C15 C13 C11 115.2(5)
C1 N5 C2 123.4(4)
C9 N2 C10 119.2(4)
C1 N4 C4 116.9(4)
C9 N1 C12 121.3(4)
H3N O3 H3M 110(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C4 N4 1.372(5)
C4 C3 1.374(6)
C4 C8 1.504(6)
C1 N4 1.315(5)
C1 N6 1.341(6)
C1 N5 1.356(5)
C5 C3 1.516(6)
C5 C7 1.516(7)
C5 C6 1.532(7)
C2 O1 1.257(5)
C2 N5 1.375(5)
C2 C3 1.423(6)
C12 C11 1.351(6)
C12 N1 1.373(6)
C12 C16 1.506(6)
C10 O2 1.253(5)
C10 N2 1.369(6)
C10 C11 1.460(6)
C11 C13 1.513(6)
C9 N2 1.319(5)
C9 N3 1.334(6)
C9 N1 1.347(5)
C13 C14 1.462(8)
C13 C15 1.481(8)
O3 H3N 0.928(16)
O3 H3M 0.932(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339293
