#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/17/2011765.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_2011765
loop_
_publ_author_name
'Low, John Nicolson'
'Marchal, Antonio'
'Nogueras, Manuel'
'Melguizo, Manuel'
'Sánchez, Adolfo'
_publ_section_title
;
 4-(1-Adamantylamino)-2-amino-6-methoxy-5-nitrosopyrimidine
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              178
_journal_page_last               179
_journal_paper_doi               10.1107/S0108270100015754
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C15 H21 N5 O2'
_chemical_formula_sum            'C15 H21 N5 O2'
_chemical_formula_weight         303.37
_chemical_name_systematic
;
4-(1-Adamantylamino)-2-amino-6-methoxy-5-nitrosopyrimidine
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.207(2)
_cell_length_b                   6.5860(4)
_cell_length_c                   7.4782(4)
_cell_measurement_reflns_used    1463
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      1.39
_cell_volume                     1438.49(15)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        DENZO
_computing_molecular_graphics    'PLATON (Spek, 2000)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_measured_fraction_theta_full .95
_diffrn_measured_fraction_theta_max .95
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .055
_diffrn_reflns_av_sigmaI/netI    .108
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8692
_diffrn_reflns_theta_full        25.93
_diffrn_reflns_theta_max         25.93
_diffrn_reflns_theta_min         1.39
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    .097
_exptl_absorpt_correction_T_max  .990
_exptl_absorpt_correction_T_min  .986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .10
_refine_diff_density_max         .37
_refine_diff_density_min         -.40
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .91
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .91
_refine_ls_R_factor_all          .146
_refine_ls_R_factor_gt           .060
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.106P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .181
_reflns_number_gt                712
_reflns_number_total             1463
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1029.cif
_cod_data_source_block           II
_cod_original_cell_volume        1438.48(16)
_cod_database_code               2011765
_cod_database_fobs_code          2011765
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x+1/2, y, -z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x, -y+1/2, z'
loop_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 .53635(12) 0.25 .4280(5) .0301(9) Uani d S 1 . . N
C2 .49034(16) 0.25 .4468(6) .0296(11) Uani d S 1 . . C
N2 .47434(12) 0.25 .6120(5) .0335(10) Uani d S 1 . . N
N3 .45796(11) 0.25 .3152(5) .0295(10) Uani d S 1 . . N
C4 .47293(15) 0.25 .1520(6) .0300(11) Uani d S 1 . . C
O4 .44369(10) 0.25 .0155(4) .0350(9) Uani d S 1 . . O
C41 .39568(15) 0.25 .0603(6) .0427(13) Uani d S 1 . . C
C5 .52116(14) 0.25 .1070(5) .0268(11) Uani d S 1 . . C
N5 .53174(13) 0.25 -.0670(5) .0342(10) Uani d S 1 . . N
O5 .57434(10) 0.25 -.1102(4) .0433(9) Uani d S 1 . . O
C6 .55148(16) 0.25 .2594(6) .0310(11) Uani d S 1 . . C
N6 .59647(12) 0.25 .2251(5) .0358(10) Uani d S 1 . . N
C61 .63514(13) 0.25 .3512(6) .0285(11) Uani d S 1 . . C
C62 .67837(13) 0.25 .2342(5) .0315(12) Uani d S 1 . . C
C63 .72111(14) 0.25 .3505(6) .0334(12) Uani d S 1 . . C
C64 .72130(10) 0.0613(5) .4683(4) .0391(9) Uani d . 1 . . C
C65 .67843(11) 0.0612(5) .5853(4) .0415(10) Uani d . 1 . . C
C66 .63532(10) 0.0603(5) .4699(4) .0344(9) Uani d . 1 . . C
C67 .67846(15) 0.25 .7044(6) .0494(15) Uani d S 1 . . C
H2A .4934 0.25 .7031 .040 Uiso calc SR 1 . . H
H2B .4446 0.25 .6310 .040 Uiso calc SR 1 . . H
H41A .3775 0.25 -.0498 .064 Uiso calc SPR .50 . . H
H41B .3885 0.3715 .1305 .064 Uiso calc PR .25 . . H
H41C .3885 0.1285 .1305 .064 Uiso calc PR .25 . . H
H41D .3921 0.25 .1906 .064 Uiso calc SPR .50 . . H
H41E .3811 0.1285 .0103 .064 Uiso calc PR .25 . . H
H41F .3811 0.3715 .0103 .064 Uiso calc PR .25 . . H
H6 .6040 0.25 .1112 .043 Uiso calc SR 1 . . H
H62A .6784 0.1283 .1565 .038 Uiso calc PR .50 . . H
H62B .6784 0.3717 .1565 .038 Uiso calc PR .50 . . H
H63 .7489 0.25 .2726 .040 Uiso calc SR 1 . . H
H64A .7490 0.0608 .5446 .047 Uiso calc R 1 . . H
H64B .7218 -0.0620 .3927 .047 Uiso calc R 1 . . H
H65 .6786 -0.0628 .6626 .050 Uiso calc R 1 . . H
H66A .6078 0.0594 .5472 .041 Uiso calc R 1 . . H
H66B .6347 -0.0632 .3945 .041 Uiso calc R 1 . . H
H67A .6510 0.25 .7820 .059 Uiso calc SR 1 . . H
H67B .7060 0.25 .7818 .059 Uiso calc SR 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C2 . . 115.3(4) no
N2 C2 N1 . . 116.7(4) no
N2 C2 N3 . . 115.4(4) no
N1 C2 N3 . . 127.9(4) no
C2 N2 H2A . . 120.0 no
C2 N2 H2B . . 120.0 no
H2A N2 H2B . . 120.0 no
C4 N3 C2 . . 116.4(4) no
N3 C4 O4 . . 120.4(4) no
N3 C4 C5 . . 123.1(4) no
O4 C4 C5 . . 116.5(4) no
C4 O4 C41 . . 116.5(3) no
O4 C41 H41A . . 109.5 no
O4 C41 H41B . . 109.5 no
H41A C41 H41B . . 109.5 no
O4 C41 H41C . . 109.5 no
H41A C41 H41C . . 109.5 no
H41B C41 H41C . . 109.5 no
O4 C41 H41D . . 109.5 no
H41A C41 H41D . . 141.1 no
H41B C41 H41D . . 56.3 no
H41C C41 H41D . . 56.3 no
O4 C41 H41E . . 109.5 no
H41A C41 H41E . . 56.3 no
H41B C41 H41E . . 141.1 no
H41C C41 H41E . . 56.3 no
H41D C41 H41E . . 109.5 no
O4 C41 H41F . . 109.5 no
H41A C41 H41F . . 56.3 no
H41B C41 H41F . . 56.3 no
H41C C41 H41F . . 141.1 no
H41D C41 H41F . . 109.5 no
H41E C41 H41F . . 109.5 no
N5 C5 C6 . . 128.8(4) no
N5 C5 C4 . . 116.8(4) no
C6 C5 C4 . . 114.4(4) no
O5 N5 C5 . . 117.9(3) yes
N1 C6 N6 . . 120.4(4) no
N1 C6 C5 . . 122.8(4) no
N6 C6 C5 . . 116.8(4) no
C6 N6 C61 . . 129.1(4) yes
C6 N6 H6 . . 115.5 no
C61 N6 H6 . . 115.5 no
N6 C61 C66 . 8_565 111.9(2) no
N6 C61 C66 . . 111.9(2) no
C66 C61 C66 8_565 . 109.2(4) no
N6 C61 C62 . . 105.4(3) no
C66 C61 C62 8_565 . 109.1(2) no
C66 C61 C62 . . 109.1(2) no
C63 C62 C61 . . 110.4(3) no
C63 C62 H62A . . 109.6 no
C61 C62 H62A . . 109.6 no
C63 C62 H62B . . 109.6 no
C61 C62 H62B . . 109.6 no
H62A C62 H62B . . 108.1 no
C62 C63 C64 . 8_565 109.5(2) no
C62 C63 C64 . . 109.5(2) no
C64 C63 C64 8_565 . 109.4(4) no
C62 C63 H63 . . 109.5 no
C64 C63 H63 8_565 . 109.5 no
C64 C63 H63 . . 109.5 no
C63 C64 C65 . . 109.2(3) no
C63 C64 H64A . . 109.8 no
C65 C64 H64A . . 109.8 no
C63 C64 H64B . . 109.8 no
C65 C64 H64B . . 109.8 no
H64A C64 H64B . . 108.3 no
C66 C65 C64 . . 110.6(3) no
C66 C65 C67 . . 109.4(3) no
C64 C65 C67 . . 109.4(3) no
C66 C65 H65 . . 109.1 no
C64 C65 H65 . . 109.1 no
C67 C65 H65 . . 109.1 no
C65 C66 C61 . . 109.1(3) no
C65 C66 H66A . . 109.9 no
C61 C66 H66A . . 109.9 no
C65 C66 H66B . . 109.9 no
C61 C66 H66B . . 109.9 no
H66A C66 H66B . . 108.3 no
C65 C67 C65 8_565 . 108.8(4) no
C65 C67 H67A 8_565 . 109.9 no
C65 C67 H67A . . 109.9 no
C65 C67 H67B 8_565 . 109.9 no
C65 C67 H67B . . 109.9 no
H67A C67 H67B . . 108.3 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 . 1.336(5) yes
N1 C2 . 1.351(5) yes
C2 N2 . 1.321(5) yes
C2 N3 . 1.364(5) yes
N2 H2A . .8800 no
N2 H2B . .8800 no
N3 C4 . 1.297(5) yes
C4 O4 . 1.330(5) no
C4 C5 . 1.448(6) yes
O4 C41 . 1.442(5) no
C41 H41A . .9800 no
C41 H41B . .9800 no
C41 H41C . .9800 no
C41 H41D . .9800 no
C41 H41E . .9800 no
C41 H41F . .9800 no
C5 N5 . 1.338(5) yes
C5 C6 . 1.443(6) yes
N5 O5 . 1.286(4) yes
C6 N6 . 1.339(5) yes
N6 C61 . 1.471(5) no
N6 H6 . .8800 no
C61 C66 8_565 1.533(4) no
C61 C66 . 1.533(4) no
C61 C62 . 1.536(5) no
C62 C63 . 1.522(5) no
C62 H62A . .9900 no
C62 H62B . .9900 no
C63 C64 8_565 1.523(4) no
C63 C64 . 1.523(4) no
C63 H63 . 1.0000 no
C64 C65 . 1.528(4) no
C64 H64A . .9900 no
C64 H64B . .9900 no
C65 C66 . 1.526(4) no
C65 C67 . 1.530(4) no
C65 H65 . 1.0000 no
C66 H66A . .9900 no
C66 H66B . .9900 no
C67 C65 8_565 1.530(4) no
C67 H67A . .9900 no
C67 H67B . .9900 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
_geom_hbond_publ_flag
N6 H6 O5 1_555 .88 1.87 2.589(5) 138 y
N2 H2A N5 1_556 .88 2.05 2.928(5) 174 y
C67 H67A O5 1_556 .99 2.38 3.342(5) 164 y
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 N2 . . 180.0 no
C6 N1 C2 N3 . . .0 no
N2 C2 N3 C4 . . 180.0 no
N1 C2 N3 C4 . . .0 no
C2 N3 C4 O4 . . 180.0 no
C2 N3 C4 C5 . . .0 no
N3 C4 O4 C41 . . .0 no
C5 C4 O4 C41 . . 180.0 no
N3 C4 C5 N5 . . 180.0 no
O4 C4 C5 N5 . . .0 no
N3 C4 C5 C6 . . .0 no
O4 C4 C5 C6 . . 180.0 no
C6 C5 N5 O5 . . .0 no
C4 C5 N5 O5 . . 180.0 no
C2 N1 C6 N6 . . 180.0 no
C2 N1 C6 C5 . . .0 no
N5 C5 C6 N1 . . 180.0 no
C4 C5 C6 N1 . . .0 no
N5 C5 C6 N6 . . .0 no
C4 C5 C6 N6 . . 180.0 no
N1 C6 N6 C61 . . .0 no
C5 C6 N6 C61 . . 180.0 no
C6 N6 C61 C66 . 8_565 -61.5(2) no
C6 N6 C61 C66 . . 61.5(2) no
C6 N6 C61 C62 . . 180.0 no
N6 C61 C62 C63 . . 180.0 no
C66 C61 C62 C63 8_565 . 59.6(2) no
C66 C61 C62 C63 . . -59.6(2) no
C61 C62 C63 C64 . 8_565 -59.9(2) no
C61 C62 C63 C64 . . 59.9(2) no
C62 C63 C64 C65 . . -59.3(4) no
C64 C63 C64 C65 8_565 . 60.7(4) no
C63 C64 C65 C66 . . 60.0(3) no
C63 C64 C65 C67 . . -60.7(4) no
C64 C65 C66 C61 . . -59.8(3) no
C67 C65 C66 C61 . . 60.8(3) no
N6 C61 C66 C65 . . 175.1(3) no
C66 C61 C66 C65 8_565 . -60.4(4) no
C62 C61 C66 C65 . . 58.8(4) no
C66 C65 C67 C65 . 8_565 -60.9(4) no
C64 C65 C67 C65 . 8_565 60.4(4) no
