##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'from SHELXL-97 with Word-Perfect Macro PRPKAPPA'
_journal_date_recd_electronic     2002-04-29
_journal_date_accepted     2002-05-03
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2002
_journal_volume     58
_journal_issue      6
_journal_page_first     o355
_journal_page_last     o358
_journal_paper_category     FO
_publ_contact_author_name     'Dr Christopher Glidewell'
_publ_contact_author_address
;
School of Chemistry
University of St Andrews
Fife KY16 9ST
Scotland
;
_publ_contact_author_email     'cg@st-andrews.ac.uk'
_publ_contact_author_fax     '+1334-463808'
_publ_contact_author_phone     '+1334-463839'
_publ_section_title
;
2-Amino-4,6-bis(benzyloxy)-5-nitrosopyrimidine: chains built from three-centre
N-H...(N,O) and N-H...π(arene) hydrogen bonds
;
loop_
    _publ_author_name
    _publ_author_address
    'Quesada, Antonio'
;
Departamento de Química Inorgánica y Orgánica
Universidad de Jaén
23071 Jaén
Spain
;
    'Low, John N.'
;
Department of Chemistry
University of Aberdeen
Meston Walk
Old Aberdeen AB24 3UE
Scotland
;
    'Melguizo, Manuel'
;
Departamento de Química Inorgánica y Orgánica
Universidad de Jaén
23071 Jaén
Spain
;
    'Nogueras, Manuel'
;
Departamento de Química Inorgánica y Orgánica
Universidad de Jaén
23071 Jaén
Spain
;
    'Glidewell, Christopher'
;
School of Chemistry
University of St Andrews
St Andrews
Fife KY16 9ST
Scotland
;
data_I
_chemical_name_systematic
;
2-Amino-4,6-bis(benzyloxy)-5-nitrosopyrimidine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H16 N4 O3'
_chemical_formula_sum     'C18 H16 N4 O3'
_chemical_formula_weight     336.35
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     11.0731(5)
_cell_length_b     7.3642(3)
_cell_length_c     22.9129(11)
_cell_angle_alpha     90
_cell_angle_beta     111.456(2)
_cell_angle_gamma     90
_cell_volume     1738.94(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3895
_cell_measurement_theta_min     2.9
_cell_measurement_theta_max     27.6
_cell_measurement_temperature     298(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     blue
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.285
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     704
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min     0.975
_exptl_absorpt_correction_T_max     0.993
_exptl_special_details
;
Data collection was carried out at room temperature because the crystals
flaked on cooling.
The program Denzo-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm
[Fox, G. C. & Holmes, K. C. (1966). Acta Cryst. 20, 886-891] which effectively
corrects for absorption effects. High-redundancy data were used in the scaling
program, hence the 'multi-scan' code word was used.
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     'φ scans, and ω scans with κ offsets'
_diffrn_reflns_number     13067
_diffrn_reflns_av_R_equivalents     0.014
_diffrn_reflns_av_sigmaI/netI     0.216
_diffrn_reflns_theta_min     2.93
_diffrn_reflns_theta_max     27.59
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.963
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     29
_diffrn_standards_decay_%     negligible
_reflns_number_total     3895
_reflns_number_gt     1203
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.264
_refine_ls_R_factor_gt     0.063
_refine_ls_wR_factor_gt     0.114
_refine_ls_wR_factor_ref     0.169
_refine_ls_goodness_of_fit_ref     0.902
_refine_ls_restrained_S_all     0.902
_refine_ls_number_reflns     3895
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                    'w = 1/[σ²(Fo²)+(0.0536P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.14
_refine_diff_density_min     -0.19
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'KappaCCD Server Software (Nonius, 1997)'
_computing_cell_refinement     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO-SMN'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2002)'
_computing_publication_material     'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
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 0.2250(3) -0.1634(3) 0.00421(13) 0.0586(8) Uani d . 1 . . N
    C2 0.1619(3) -0.1771(5) 0.04435(17) 0.0597(9) Uani d . 1 . . C
    N2 0.1348(3) -0.3428(4) 0.05732(14) 0.0861(11) Uani d . 1 . . N
    N3 0.1232(3) -0.0393(3) 0.07247(12) 0.0591(8) Uani d . 1 . . N
    C4 0.1563(3) 0.1226(4) 0.05998(15) 0.0531(9) Uani d . 1 . . C
    O4 0.1272(2) 0.2660(3) 0.08853(10) 0.0641(7) Uani d . 1 . . O
    C47 0.0702(4) 0.2280(4) 0.13540(17) 0.0708(11) Uani d . 1 . . C
    C41 0.0557(4) 0.4087(4) 0.16239(17) 0.0555(9) Uani d . 1 . . C
    C42 -0.0578(4) 0.5044(5) 0.13773(17) 0.0667(10) Uani d . 1 . . C
    C43 -0.0697(4) 0.6740(5) 0.1610(2) 0.0800(12) Uani d . 1 . . C
    C44 0.0316(6) 0.7469(6) 0.2091(2) 0.0868(14) Uani d . 1 . . C
    C45 0.1440(5) 0.6533(6) 0.2343(2) 0.0903(13) Uani d . 1 . . C
    C46 0.1576(4) 0.4845(5) 0.21121(18) 0.0746(11) Uani d . 1 . . C
    C5 0.2240(3) 0.1590(4) 0.01983(14) 0.0496(8) Uani d . 1 . . C
    N5 0.2524(3) 0.3375(4) 0.01281(13) 0.0610(8) Uani d . 1 . . N
    O5 0.3201(2) 0.3712(3) -0.01890(12) 0.0758(8) Uani d . 1 . . O
    C6 0.2565(3) 0.0008(4) -0.00656(15) 0.0525(9) Uani d . 1 . . C
    O6 0.3226(2) 0.0224(3) -0.04448(11) 0.0660(7) Uani d . 1 . . O
    C67 0.3601(4) -0.1411(5) -0.06850(19) 0.0815(12) Uani d . 1 . . C
    C61 0.4320(4) -0.0870(6) -0.10946(18) 0.0732(11) Uani d . 1 . . C
    C62 0.4577(4) 0.0886(7) -0.11957(18) 0.0896(13) Uani d . 1 . . C
    C63 0.5258(5) 0.1308(9) -0.1582(2) 0.1207(19) Uani d . 1 . . C
    C64 0.5695(6) -0.0060(13) -0.1862(3) 0.149(3) Uani d . 1 . . C
    C65 0.5435(6) -0.1804(12) -0.1766(3) 0.139(3) Uani d . 1 . . C
    C66 0.4765(4) -0.2256(7) -0.1381(2) 0.0962(14) Uani d . 1 . . C
    H2A 0.1572 -0.4346 0.0404 0.103 Uiso calc R 1 . . H
    H2B 0.0946 -0.3592 0.0827 0.103 Uiso calc R 1 . . H
    H47A 0.1263 0.1490 0.1679 0.085 Uiso calc R 1 . . H
    H47B -0.0137 0.1697 0.1162 0.085 Uiso calc R 1 . . H
    H42 -0.1274 0.4550 0.1051 0.080 Uiso calc R 1 . . H
    H43 -0.1469 0.7383 0.1438 0.096 Uiso calc R 1 . . H
    H44 0.0235 0.8610 0.2246 0.104 Uiso calc R 1 . . H
    H45 0.2126 0.7031 0.2673 0.108 Uiso calc R 1 . . H
    H46 0.2354 0.4215 0.2286 0.090 Uiso calc R 1 . . H
    H67A 0.2837 -0.2109 -0.0924 0.098 Uiso calc R 1 . . H
    H67B 0.4149 -0.2156 -0.0341 0.098 Uiso calc R 1 . . H
    H62 0.4293 0.1818 -0.1004 0.108 Uiso calc R 1 . . H
    H63 0.5417 0.2514 -0.1650 0.145 Uiso calc R 1 . . H
    H64 0.6164 0.0212 -0.2115 0.179 Uiso calc R 1 . . H
    H65 0.5714 -0.2726 -0.1964 0.166 Uiso calc R 1 . . H
    H66 0.4612 -0.3466 -0.1315 0.115 Uiso calc R 1 . . H
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
    C6 N1 . 1.306(4) y
    N1 C2 . 1.347(4) y
    C2 N3 . 1.353(4) y
    N3 C4 . 1.310(4) y
    C4 C5 . 1.408(4) y
    C5 C6 . 1.419(4) y
    C2 N2 . 1.316(4) y
    C4 O4 . 1.342(3) y
    C6 O6 . 1.334(4) y
    C5 N5 . 1.374(4) y
    N5 O5 . 1.245(3) y
    N2 H2A . 0.8600 no
    N2 H2B . 0.8600 no
    O4 C47 . 1.458(4) no
    C47 C41 . 1.500(4) no
    C47 H47A . 0.9700 no
    C47 H47B . 0.9700 no
    C41 C42 . 1.369(5) no
    C41 C46 . 1.383(5) no
    C42 C43 . 1.383(5) no
    C42 H42 . 0.9300 no
    C43 C44 . 1.362(5) no
    C43 H43 . 0.9300 no
    C44 C45 . 1.353(6) no
    C44 H44 . 0.9300 no
    C45 C46 . 1.380(5) no
    C45 H45 . 0.9300 no
    C46 H46 . 0.9300 no
    O6 C67 . 1.446(4) no
    C67 C61 . 1.490(5) no
    C67 H67A . 0.9700 no
    C67 H67B . 0.9700 no
    C61 C62 . 1.363(5) no
    C61 C66 . 1.397(5) no
    C62 C63 . 1.392(6) no
    C62 H62 . 0.9300 no
    C63 C64 . 1.374(8) no
    C63 H63 . 0.9300 no
    C64 C65 . 1.352(8) no
    C64 H64 . 0.9300 no
    C65 C66 . 1.385(7) no
    C65 H65 . 0.9300 no
    C66 H66 . 0.9300 no
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 . . 116.1(3) no
    N2 C2 N1 . . 116.2(3) no
    N2 C2 N3 . . 116.7(3) no
    N1 C2 N3 . . 127.1(3) no
    C2 N2 H2A . . 120.0 no
    C2 N2 H2B . . 120.0 no
    H2A N2 H2B . . 120.0 no
    C4 N3 C2 . . 114.6(3) no
    N3 C4 O4 . . 118.2(3) no
    N3 C4 C5 . . 125.1(3) no
    O4 C4 C5 . . 116.6(3) no
    C4 O4 C47 . . 117.0(2) no
    O4 C47 C41 . . 105.9(2) no
    O4 C47 H47A . . 110.6 no
    C41 C47 H47A . . 110.6 no
    O4 C47 H47B . . 110.6 no
    C41 C47 H47B . . 110.6 no
    H47A C47 H47B . . 108.7 no
    C42 C41 C46 . . 118.7(3) no
    C42 C41 C47 . . 120.4(4) no
    C46 C41 C47 . . 120.9(4) no
    C41 C42 C43 . . 120.5(4) no
    C41 C42 H42 . . 119.7 no
    C43 C42 H42 . . 119.7 no
    C44 C43 C42 . . 120.1(4) no
    C44 C43 H43 . . 120.0 no
    C42 C43 H43 . . 120.0 no
    C45 C44 C43 . . 120.0(4) no
    C45 C44 H44 . . 120.0 no
    C43 C44 H44 . . 120.0 no
    C44 C45 C46 . . 120.5(4) no
    C44 C45 H45 . . 119.7 no
    C46 C45 H45 . . 119.7 no
    C45 C46 C41 . . 120.1(4) no
    C45 C46 H46 . . 119.9 no
    C41 C46 H46 . . 119.9 no
    N5 C5 C4 . . 117.3(3) no
    N5 C5 C6 . . 129.1(3) no
    C4 C5 C6 . . 113.6(3) no
    O5 N5 C5 . . 118.2(3) no
    N1 C6 O6 . . 118.8(3) no
    N1 C6 C5 . . 123.5(3) no
    O6 C6 C5 . . 117.7(3) no
    C6 O6 C67 . . 116.8(3) no
    O6 C67 C61 . . 108.1(3) no
    O6 C67 H67A . . 110.1 no
    C61 C67 H67A . . 110.1 no
    O6 C67 H67B . . 110.1 no
    C61 C67 H67B . . 110.1 no
    H67A C67 H67B . . 108.4 no
    C62 C61 C66 . . 118.8(4) no
    C62 C61 C67 . . 123.6(4) no
    C66 C61 C67 . . 117.6(4) no
    C61 C62 C63 . . 121.0(5) no
    C61 C62 H62 . . 119.5 no
    C63 C62 H62 . . 119.5 no
    C64 C63 C62 . . 120.0(6) no
    C64 C63 H63 . . 120.0 no
    C62 C63 H63 . . 120.0 no
    C65 C64 C63 . . 119.2(7) no
    C65 C64 H64 . . 120.4 no
    C63 C64 H64 . . 120.4 no
    C64 C65 C66 . . 121.8(7) no
    C64 C65 H65 . . 119.1 no
    C66 C65 H65 . . 119.1 no
    C65 C66 C61 . . 119.2(5) no
    C65 C66 H66 . . 120.4 no
    C61 C66 H66 . . 120.4 no
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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 N1 C2 N2 . . . . -177.3(3) no
    C6 N1 C2 N3 . . . . 3.0(5) no
    N2 C2 N3 C4 . . . . 177.6(3) no
    N1 C2 N3 C4 . . . . -2.6(5) no
    C2 N3 C4 O4 . . . . -176.7(3) no
    C2 N3 C4 C5 . . . . 1.5(5) no
    N3 C4 O4 C47 . . . . 4.9(4) no
    C5 C4 O4 C47 . . . . -173.4(3) no
    C4 O4 C47 C41 . . . . 176.4(3) no
    O4 C47 C41 C42 . . . . 92.6(4) no
    O4 C47 C41 C46 . . . . -85.3(4) no
    C46 C41 C42 C43 . . . . 0.4(5) no
    C47 C41 C42 C43 . . . . -177.6(3) no
    C41 C42 C43 C44 . . . . -0.4(6) no
    C42 C43 C44 C45 . . . . -0.1(6) no
    C43 C44 C45 C46 . . . . 0.6(7) no
    C44 C45 C46 C41 . . . . -0.5(6) no
    C42 C41 C46 C45 . . . . 0.0(6) no
    C47 C41 C46 C45 . . . . 178.0(3) no
    N3 C4 C5 N5 . . . . -179.1(3) no
    O4 C4 C5 N5 . . . . -0.9(4) no
    N3 C4 C5 C6 . . . . -0.8(5) no
    O4 C4 C5 C6 . . . . 177.4(3) no
    C4 C5 N5 O5 . . . . 175.0(3) no
    C6 C5 N5 O5 . . . . -3.0(5) no
    C2 N1 C6 O6 . . . . 178.0(3) no
    C2 N1 C6 C5 . . . . -2.1(5) no
    N5 C5 C6 N1 . . . . 179.2(3) no
    C4 C5 C6 N1 . . . . 1.2(5) no
    N5 C5 C6 O6 . . . . -1.0(5) no
    C4 C5 C6 O6 . . . . -179.0(3) no
    N1 C6 O6 C67 . . . . -3.0(4) no
    C5 C6 O6 C67 . . . . 177.1(3) no
    C6 O6 C67 C61 . . . . 179.9(3) no
    O6 C67 C61 C62 . . . . 1.4(5) no
    O6 C67 C61 C66 . . . . -179.5(3) no
    C66 C61 C62 C63 . . . . 0.7(7) no
    C67 C61 C62 C63 . . . . 179.7(4) no
    C61 C62 C63 C64 . . . . -0.7(8) no
    C62 C63 C64 C65 . . . . 1.1(9) no
    C63 C64 C65 C66 . . . . -1.5(10) no
    C64 C65 C66 C61 . . . . 1.4(8) no
    C62 C61 C66 C65 . . . . -1.0(6) no
    C67 C61 C66 C65 . . . . 179.9(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
    _geom_hbond_publ_flag
    N2 H2A O4 1_545 0.86 2.54 2.977(4) 112 y
    N2 H2A N5 1_545 0.86 2.19 3.041(4) 168 y
    N2 H2B Cg2 1_545 0.86 2.67 3.496(4) 163 y
