#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:00:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178455 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/76/4027647.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_4027647
loop_
_publ_author_name
'Borys Ośmiałowski'
'Erkki Kolehmainen'
'Satu Ikonen'
'Arto Valkonen'
'Adam Kwiatkowski'
'Izabela Grela'
'Esa Haapaniemi'
_publ_section_title
;
 2-Acylamino- and 2,4-Bis(acylamino)pyrimidines as Supramolecular Synthons
 Analyzed by Multiple Noncovalent Interactions. DFT, X-ray Diffraction,
 and NMR Spectral Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9609
_journal_page_last               9619
_journal_paper_doi               10.1021/jo301643z
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C6 H7 N3 O'
_chemical_formula_weight         137.15
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                68.847(3)
_cell_angle_beta                 80.100(3)
_cell_angle_gamma                71.118(3)
_cell_formula_units_Z            2
_cell_length_a                   5.6718(2)
_cell_length_b                   7.7144(4)
_cell_length_c                   8.1495(3)
_cell_measurement_reflns_used    1263
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407
_cell_volume                     314.04(2)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker, 2004)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL-97; MERCURY (Macrae, et al., 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-2002 (Burla, et al., 2003)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker Kappa APEX-II'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2050
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       plate
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0784P)²+0.1794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                1182
_reflns_number_total             1276
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo301643z_si_001.cif
_cod_data_source_block           13me
_cod_database_code               4027647
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.0119(3) 0.16131(19) 0.14028(18) 0.0221(4) Uani 1 1 d .
H1N H -0.064(4) 0.084(3) 0.124(3) 0.033 Uiso 1 1 d .
N2 N 0.3082(3) 0.33446(19) 0.00423(18) 0.0228(4) Uani 1 1 d .
O1 O -0.2374(2) 0.15316(17) 0.38580(15) 0.0273(4) Uani 1 1 d .
N6 N 0.2253(2) 0.11835(19) -0.11301(17) 0.0216(4) Uani 1 1 d .
C4 C 0.5250(3) 0.2890(2) -0.2626(2) 0.0255(4) Uani 1 1 d .
H4 H 0.6430 0.3189 -0.3586 0.031 Uiso 1 1 calc R
C3 C 0.4753(3) 0.3717(2) -0.1313(2) 0.0250(4) Uani 1 1 d .
H3 H 0.5642 0.4594 -0.1375 0.030 Uiso 1 1 calc R
C7 C -0.0597(3) 0.2035(2) 0.2955(2) 0.0217(4) Uani 1 1 d .
C1 C 0.1905(3) 0.2081(2) 0.0071(2) 0.0201(4) Uani 1 1 d .
C8 C 0.0810(3) 0.3061(2) 0.3509(2) 0.0251(4) Uani 1 1 d .
H8A H 0.2149 0.3349 0.2613 0.038 Uiso 0.50 1 calc PR
H8B H 0.1533 0.2229 0.4639 0.038 Uiso 0.50 1 calc PR
H8C H -0.0333 0.4273 0.3637 0.038 Uiso 0.50 1 calc PR
H8D H 0.0084 0.3218 0.4646 0.038 Uiso 0.50 1 calc PR
H8E H 0.0700 0.4339 0.2621 0.038 Uiso 0.50 1 calc PR
H8F H 0.2566 0.2294 0.3622 0.038 Uiso 0.50 1 calc PR
C5 C 0.3931(3) 0.1599(2) -0.2468(2) 0.0229(4) Uani 1 1 d .
H5 H 0.4232 0.0990 -0.3339 0.028 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0254(7) 0.0207(7) 0.0243(7) -0.0087(5) 0.0021(5) -0.0123(5)
N2 0.0265(7) 0.0206(7) 0.0244(7) -0.0080(5) 0.0012(5) -0.0115(5)
O1 0.0283(6) 0.0301(7) 0.0271(6) -0.0112(5) 0.0060(5) -0.0149(5)
N6 0.0242(7) 0.0201(7) 0.0223(7) -0.0071(5) -0.0002(5) -0.0089(5)
C4 0.0254(8) 0.0262(8) 0.0249(8) -0.0067(6) 0.0031(6) -0.0116(6)
C3 0.0258(8) 0.0238(8) 0.0274(8) -0.0069(6) 0.0007(6) -0.0127(6)
C7 0.0226(7) 0.0184(7) 0.0235(7) -0.0062(6) 0.0000(6) -0.0064(6)
C1 0.0211(7) 0.0173(7) 0.0215(7) -0.0050(6) -0.0017(6) -0.0064(6)
C8 0.0278(8) 0.0285(8) 0.0241(8) -0.0125(6) 0.0020(6) -0.0121(7)
C5 0.0249(8) 0.0224(8) 0.0214(8) -0.0074(6) -0.0002(6) -0.0068(6)
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
C7 N1 C1 131.91(14)
C7 N1 H1N 115.2(14)
C1 N1 H1N 112.8(14)
C3 N2 C1 115.72(14)
C5 N6 C1 116.49(13)
C3 C4 C5 116.31(15)
C3 C4 H4 121.8
C5 C4 H4 121.8
N2 C3 C4 123.27(15)
N2 C3 H3 118.4
C4 C3 H3 118.4
O1 C7 N1 118.15(14)
O1 C7 C8 121.73(14)
N1 C7 C8 120.12(14)
N2 C1 N6 125.98(14)
N2 C1 N1 120.40(14)
N6 C1 N1 113.61(13)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C7 C8 H8D 109.5
H8A C8 H8D 141.1
H8B C8 H8D 56.3
H8C C8 H8D 56.3
C7 C8 H8E 109.5
H8A C8 H8E 56.3
H8B C8 H8E 141.1
H8C C8 H8E 56.3
H8D C8 H8E 109.5
C7 C8 H8F 109.5
H8A C8 H8F 56.3
H8B C8 H8F 56.3
H8C C8 H8F 141.1
H8D C8 H8F 109.5
H8E C8 H8F 109.5
N6 C5 C4 122.23(14)
N6 C5 H5 118.9
C4 C5 H5 118.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.380(2)
N1 C1 1.382(2)
N1 H1N 0.90(2)
N2 C3 1.337(2)
N2 C1 1.340(2)
O1 C7 1.2247(19)
N6 C5 1.336(2)
N6 C1 1.345(2)
C4 C3 1.380(2)
C4 C5 1.387(2)
C4 H4 0.9500
C3 H3 0.9500
C7 C8 1.503(2)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C8 H8D 0.9800
C8 H8E 0.9800
C8 H8F 0.9800
C5 H5 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N6 0.90(2) 2.08(2) 2.9734(19) 174(2) 2
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
C1 N2 C3 C4 0.7(2)
C5 C4 C3 N2 -0.8(3)
C1 N1 C7 O1 175.42(15)
C1 N1 C7 C8 -5.4(3)
C3 N2 C1 N6 -0.3(2)
C3 N2 C1 N1 -179.19(13)
C5 N6 C1 N2 0.1(2)
C5 N6 C1 N1 179.02(12)
C7 N1 C1 N2 -8.9(3)
C7 N1 C1 N6 172.05(15)
C1 N6 C5 C4 -0.2(2)
C3 C4 C5 N6 0.6(2)
