#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/52/2015281.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2015281
loop_
_publ_author_name
'Kanda Panthong'
'Mary J. Garson'
'Paul V. Bernhardt'
_publ_section_title
;
 1,3-Dimethylisoguanine
;
_journal_coeditor_code           SQ1243
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o193
_journal_page_last               o195
_journal_paper_doi               10.1107/S0108270106005336
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C7 H9 N5 O1'
_chemical_formula_moiety         'C7 H9 N5 O1'
_chemical_formula_sum            'C7 H9 N5 O'
_chemical_formula_weight         179.19
_chemical_name_common
;
1,3-Dimethylisoguanine
;
_chemical_name_systematic
;
6-amino-1,3-dimethyl-1H-purin-2(3H)-one
;
_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_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 96.370(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9352(9)
_cell_length_b                   6.1050(6)
_cell_length_c                   14.678(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.515
_cell_measurement_theta_min      8.313
_cell_volume                     795.73(16)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Version 1.70; Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       κ-geometry
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'Non-profiled ω/2θ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1427
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            1473
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        -3
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.00
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.00
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0895P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.136
_refine_ls_wR_factor_ref         0.1662
_reflns_number_gt                771
_reflns_number_total             1380
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq1243.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C7 H9 N5 O1'
_cod_database_code               2015281
_cod_database_fobs_code          2015281
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C2 0.1524(4) -0.0738(6) 0.6013(2) 0.0348(9) Uani d . 1
C C4 0.2709(4) 0.2391(6) 0.6739(2) 0.0309(8) Uani d . 1
C C5 0.3393(4) 0.2893(6) 0.5963(2) 0.0323(9) Uani d . 1
C C6 0.3145(4) 0.1618(6) 0.5181(2) 0.0316(9) Uani d . 1
C C8 0.3947(4) 0.5266(6) 0.6985(2) 0.0379(9) Uani d . 1
H H8 0.4357 0.6506 0.7284 0.045 Uiso calc R 1
C C10 0.2011(4) -0.1688(6) 0.4459(2) 0.0443(10) Uani d . 1
H H10A 0.1499 -0.0942 0.3939 0.066 Uiso calc R 1
H H10B 0.1415 -0.2909 0.4618 0.066 Uiso calc R 1
H H10C 0.2969 -0.2204 0.431 0.066 Uiso calc R 1
C C12 0.1197(4) -0.0092(6) 0.7608(2) 0.0438(10) Uani d . 1
H H12A 0.0119 -0.0168 0.7497 0.066 Uiso calc R 1
H H12B 0.148 0.0959 0.8082 0.066 Uiso calc R 1
H H12C 0.159 -0.1504 0.7795 0.066 Uiso calc R 1
N N1 0.2239(3) -0.0183(5) 0.52332(17) 0.0330(7) Uani d . 1
N N3 0.1807(3) 0.0574(5) 0.67685(17) 0.0329(7) Uani d . 1
N N7 0.4217(3) 0.4795(5) 0.61344(18) 0.0380(8) Uani d . 1
N N9 0.3047(3) 0.3871(5) 0.74031(18) 0.0332(7) Uani d . 1
N N13 0.3733(4) 0.2020(7) 0.4410(2) 0.0411(9) Uani d . 1
O O2 0.0693(3) -0.2322(5) 0.60014(17) 0.0480(8) Uani d . 1
H H3A 0.345(4) 0.141(7) 0.390(3) 0.055(13) Uiso d . 1
H H3B 0.427(4) 0.322(7) 0.435(2) 0.038(11) Uiso d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C2 0.0344(19) 0.038(2) 0.0330(19) -0.0022(18) 0.0084(15) 0.0029(17)
C4 0.0332(19) 0.036(2) 0.0250(16) 0.0033(17) 0.0090(15) 0.0011(16)
C5 0.0341(19) 0.041(2) 0.0237(17) -0.0006(18) 0.0101(15) 0.0012(16)
C6 0.0328(18) 0.038(2) 0.0248(17) 0.0029(17) 0.0082(14) 0.0041(16)
C8 0.043(2) 0.040(2) 0.0315(18) -0.0030(19) 0.0080(16) -0.0028(18)
C10 0.060(2) 0.046(2) 0.0294(18) -0.008(2) 0.0149(17) -0.0078(18)
C12 0.060(2) 0.045(2) 0.0294(18) -0.006(2) 0.0204(17) 0.0064(18)
N1 0.0401(16) 0.0365(18) 0.0236(14) -0.0052(15) 0.0088(12) -0.0029(13)
N3 0.0421(16) 0.0359(18) 0.0227(14) -0.0052(14) 0.0126(12) 0.0020(13)
N7 0.0422(17) 0.047(2) 0.0264(15) -0.0070(16) 0.0106(12) -0.0015(14)
N9 0.0371(15) 0.0388(18) 0.0254(15) -0.0003(14) 0.0109(12) 0.0006(13)
N13 0.053(2) 0.050(2) 0.0223(16) -0.0120(18) 0.0137(14) -0.0036(16)
O2 0.0587(17) 0.0479(17) 0.0407(14) -0.0146(15) 0.0195(13) -0.0047(13)
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 -1 8
-5 1 -1
-1 -3 -5
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O2 C2 N3 122.2(3) no
O2 C2 N1 120.6(3) no
N3 C2 N1 117.2(3) no
N9 C4 N3 127.5(3) no
N9 C4 C5 111.4(3) no
N3 C4 C5 121.2(3) no
N7 C5 C6 131.0(3) no
N7 C5 C4 108.1(3) no
C6 C5 C4 120.8(3) no
N13 C6 N1 119.3(3) no
N13 C6 C5 124.2(3) no
N1 C6 C5 116.5(3) no
N7 C8 N9 117.7(3) no
N7 C8 H8 121.1 no
N9 C8 H8 121.1 no
N1 C10 H10A 109.5 no
N1 C10 H10B 109.5 no
H10A C10 H10B 109.5 no
N1 C10 H10C 109.5 no
H10A C10 H10C 109.5 no
H10B C10 H10C 109.5 no
N3 C12 H12A 109.5 no
N3 C12 H12B 109.5 no
H12A C12 H12B 109.5 no
N3 C12 H12C 109.5 no
H12A C12 H12C 109.5 no
H12B C12 H12C 109.5 no
C6 N1 C2 124.1(3) no
C6 N1 C10 119.6(3) no
C2 N1 C10 116.3(3) no
C2 N3 C4 120.2(3) no
C2 N3 C12 117.9(3) no
C4 N3 C12 121.7(3) no
C8 N7 C5 101.8(3) no
C4 N9 C8 101.0(3) no
C6 N13 H3A 124(3) no
C6 N13 H3B 120(2) no
H3A N13 H3B 113(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 O2 1.218(4) yes
C2 N3 1.368(5) yes
C2 N1 1.413(4) yes
C4 N9 1.339(4) yes
C4 N3 1.375(4) yes
C4 C5 1.386(4) yes
C5 N7 1.383(4) yes
C5 C6 1.384(5) yes
C6 N13 1.322(4) yes
C6 N1 1.372(4) yes
C8 N7 1.329(4) yes
C8 N9 1.363(4) yes
C8 H8 0.9300 no
C10 N1 1.458(4) yes
C10 H10A 0.9600 no
C10 H10B 0.9600 no
C10 H10C 0.9600 no
C12 N3 1.459(4) yes
C12 H12A 0.9600 no
C12 H12B 0.9600 no
C12 H12C 0.9600 no
N13 H3A 0.85(5) no
N13 H3B 0.88(4) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N13 H3A N9 4_565 0.85(5) 2.20(5) 2.992(4) 156(4)
N13 H3B N7 3_666 0.88(4) 2.01(4) 2.846(5) 158(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4421937
