#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/27/2012723.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_2012723
loop_
_publ_author_name
'Low, John N.'
'Quesada, Antonio'
'Marchal, Antonio'
'Melguizo, Manuel'
'Nogueras, Manuel'
'Glidewell, Christopher'
_publ_section_title
;
 Hydrogen bonding in 2-amino-4,6-dimethoxypyrimidine,
 2-benzylamino-4,6-bis(benzyloxy)pyrimidine and
 2-amino-4,6-bis(N-pyrrolidino)pyrimidine: chains of fused rings
 and a centrosymmetric dimer
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o289
_journal_page_last               o294
_journal_paper_doi               10.1107/S0108270102005632
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C12 H19 N5'
_chemical_formula_sum            'C12 H19 N5'
_chemical_formula_weight         233.32
_chemical_name_systematic
;
2-amino-4,6-bis(N-pyrrolidino)pyrimidine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_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
_cell_angle_alpha                90
_cell_angle_beta                 93.090(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5654(8)
_cell_length_b                   13.2735(8)
_cell_length_c                   14.2279(9)
_cell_measurement_reflns_used    2485
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      2.23
_cell_volume                     2369.6(3)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'PLATON (Spek, 2002)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7257
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO-SMN; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0753P)²+0.6604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.113
_refine_ls_wR_factor_ref         0.117
_reflns_number_gt                2109
_reflns_number_total             2485
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1546.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2012723
_cod_database_fobs_code          2012723
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -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'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z+1/2'
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 0.14234(7) 0.42768(7) 0.04220(6) 0.0167(2) Uani d . 1 . . N
C2 0.08934(9) 0.41017(8) 0.12032(8) 0.0169(3) Uani d . 1 . . C
N2 -0.01134(8) 0.44606(8) 0.12240(7) 0.0226(3) Uani d . 1 . . N
N3 0.12512(7) 0.36133(7) 0.19908(6) 0.0177(2) Uani d . 1 . . N
C4 0.22452(9) 0.32333(8) 0.19736(8) 0.0168(3) Uani d . 1 . . C
N4 0.25920(7) 0.27045(8) 0.27487(7) 0.0210(3) Uani d . 1 . . N
C41 0.19010(9) 0.24157(9) 0.34986(8) 0.0200(3) Uani d . 1 . . C
C42 0.25113(10) 0.15405(9) 0.39630(9) 0.0247(3) Uani d . 1 . . C
C43 0.36722(10) 0.18595(10) 0.38874(9) 0.0248(3) Uani d . 1 . . C
C44 0.36740(9) 0.23140(9) 0.28994(8) 0.0203(3) Uani d . 1 . . C
C5 0.28893(9) 0.33753(8) 0.12149(8) 0.0181(3) Uani d . 1 . . C
C6 0.24377(9) 0.39189(8) 0.04469(8) 0.0163(3) Uani d . 1 . . C
N6 0.30145(7) 0.41109(7) -0.03098(7) 0.0190(2) Uani d . 1 . . N
C61 0.41069(9) 0.37530(9) -0.03849(8) 0.0193(3) Uani d . 1 . . C
C62 0.44028(10) 0.41074(9) -0.13600(8) 0.0228(3) Uani d . 1 . . C
C63 0.36687(9) 0.50100(9) -0.15631(8) 0.0216(3) Uani d . 1 . . C
C64 0.26383(9) 0.47094(9) -0.11223(8) 0.0188(3) Uani d . 1 . . C
H2A -0.0398 0.4794 0.0738 0.027 Uiso calc R 1 . . H
H2B -0.0484 0.4360 0.1723 0.027 Uiso calc R 1 . . H
H41A 0.1190 0.2200 0.3240 0.024 Uiso calc R 1 . . H
H41B 0.1814 0.2976 0.3947 0.024 Uiso calc R 1 . . H
H42A 0.2360 0.0901 0.3623 0.030 Uiso calc R 1 . . H
H42B 0.2334 0.1461 0.4628 0.030 Uiso calc R 1 . . H
H43A 0.4158 0.1273 0.3950 0.030 Uiso calc R 1 . . H
H43B 0.3885 0.2365 0.4374 0.030 Uiso calc R 1 . . H
H44A 0.4207 0.2861 0.2871 0.024 Uiso calc R 1 . . H
H44B 0.3827 0.1794 0.2426 0.024 Uiso calc R 1 . . H
H5 0.3595 0.3118 0.1218 0.022 Uiso calc R 1 . . H
H61A 0.4142 0.3010 -0.0336 0.023 Uiso calc R 1 . . H
H61B 0.4589 0.4051 0.0114 0.023 Uiso calc R 1 . . H
H62A 0.4272 0.3570 -0.1835 0.027 Uiso calc R 1 . . H
H62B 0.5161 0.4311 -0.1355 0.027 Uiso calc R 1 . . H
H63A 0.3970 0.5631 -0.1270 0.026 Uiso calc R 1 . . H
H63B 0.3550 0.5120 -0.2249 0.026 Uiso calc R 1 . . H
H64A 0.2238 0.5309 -0.0926 0.023 Uiso calc R 1 . . H
H64B 0.2178 0.4305 -0.1565 0.023 Uiso calc R 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 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'
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
C2 N1 C6 115.03(10) no
N1 C2 N3 127.63(10) no
N1 C2 N2 117.50(10) no
N3 C2 N2 114.87(10) no
C2 N2 H2A 120.0 no
C2 N2 H2B 120.0 no
H2A N2 H2B 120.0 no
C4 N3 C2 115.58(10) no
N3 C4 N4 115.80(10) no
N3 C4 C5 122.65(10) no
N4 C4 C5 121.55(10) no
C4 N4 C41 123.39(9) y
C4 N4 C44 123.91(10) y
C41 N4 C44 112.62(9) y
N4 C41 C42 102.22(9) no
N4 C41 H41A 111.3 no
C42 C41 H41A 111.3 no
N4 C41 H41B 111.3 no
C42 C41 H41B 111.3 no
H41A C41 H41B 109.2 no
C41 C42 C43 102.61(9) no
C41 C42 H42A 111.2 no
C43 C42 H42A 111.2 no
C41 C42 H42B 111.2 no
C43 C42 H42B 111.2 no
H42A C42 H42B 109.2 no
C42 C43 C44 102.87(9) no
C42 C43 H43A 111.2 no
C44 C43 H43A 111.2 no
C42 C43 H43B 111.2 no
C44 C43 H43B 111.2 no
H43A C43 H43B 109.1 no
N4 C44 C43 103.14(9) no
N4 C44 H44A 111.1 no
C43 C44 H44A 111.1 no
N4 C44 H44B 111.1 no
C43 C44 H44B 111.1 no
H44A C44 H44B 109.1 no
C4 C5 C6 116.39(10) no
C4 C5 H5 121.8 no
C6 C5 H5 121.8 no
N6 C6 N1 117.06(10) no
N6 C6 C5 120.30(10) no
N1 C6 C5 122.64(10) no
C6 N6 C61 122.82(9) y
C6 N6 C64 124.58(9) y
C61 N6 C64 112.58(9) y
N6 C61 C62 103.98(9) no
N6 C61 H61A 111.0 no
C62 C61 H61A 111.0 no
N6 C61 H61B 111.0 no
C62 C61 H61B 111.0 no
H61A C61 H61B 109.0 no
C61 C62 C63 103.80(9) no
C61 C62 H62A 111.0 no
C63 C62 H62A 111.0 no
C61 C62 H62B 111.0 no
C63 C62 H62B 111.0 no
H62A C62 H62B 109.0 no
C64 C63 C62 103.56(9) no
C64 C63 H63A 111.0 no
C62 C63 H63A 111.0 no
C64 C63 H63B 111.0 no
C62 C63 H63B 111.0 no
H63A C63 H63B 109.0 no
N6 C64 C63 102.86(9) no
N6 C64 H64A 111.2 no
C63 C64 H64A 111.2 no
N6 C64 H64B 111.2 no
C63 C64 H64B 111.2 no
H64A C64 H64B 109.1 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 C2 . 1.3464(15) y
C2 N3 . 1.3506(14) y
N3 C4 . 1.3484(15) y
C4 C5 . 1.3965(16) y
C5 C6 . 1.4035(15) y
C6 N1 . 1.3588(14) y
C2 N2 . 1.3537(15) y
N2 H2A . 0.8800 no
N2 H2B . 0.8800 no
C4 N4 . 1.3590(14) y
N4 C44 . 1.4601(14) no
N4 C41 . 1.4625(15) no
C41 C42 . 1.5230(16) no
C41 H41A . 0.9900 no
C41 H41B . 0.9900 no
C42 C43 . 1.5283(18) no
C42 H42A . 0.9900 no
C42 H42B . 0.9900 no
C43 C44 . 1.5298(16) no
C43 H43A . 0.9900 no
C43 H43B . 0.9900 no
C44 H44A . 0.9900 no
C44 H44B . 0.9900 no
C5 H5 . 0.9500 no
C6 N6 . 1.3540(15) y
N6 C64 . 1.4602(14) no
N6 C61 . 1.4619(14) no
C61 C62 . 1.5296(16) no
C61 H61A . 0.9900 no
C61 H61B . 0.9900 no
C62 C63 . 1.5300(16) no
C62 H62A . 0.9900 no
C62 H62B . 0.9900 no
C63 C64 . 1.5219(16) no
C63 H63A . 0.9900 no
C63 H63B . 0.9900 no
C64 H64A . 0.9900 no
C64 H64B . 0.9900 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
N2 H2A N1 3_565 0.88 2.38 3.2538(14) 170 y
N2 H2B N3 2_555 0.88 2.33 3.1862(13) 163 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
_geom_torsion_publ_flag
C6 N1 C2 N3 -0.43(17) no
C6 N1 C2 N2 178.66(9) no
N1 C2 N3 C4 -2.19(17) no
N2 C2 N3 C4 178.70(9) no
C2 N3 C4 N4 -177.32(9) no
C2 N3 C4 C5 3.17(16) no
N3 C4 N4 C44 -174.24(10) no
N3 C4 N4 C41 9.39(16) y
C5 C4 N4 C44 5.27(17) y
C5 C4 N4 C41 -171.10(11) no
C4 N4 C41 C42 158.93(11) no
N4 C41 C42 C43 35.48(12) y
C41 C42 C43 C44 -40.59(12) y
C42 C43 C44 N4 29.44(12) y
C43 C44 N4 C41 -7.37(13) y
C44 N4 C41 C42 -17.80(13) y
C4 N4 C44 C43 175.92(11) no
N3 C4 C5 C6 -1.63(16) no
N4 C4 C5 C6 178.90(10) no
C2 N1 C6 N6 -177.58(9) no
C2 N1 C6 C5 2.18(16) no
C4 C5 C6 N6 178.52(10) no
C4 C5 C6 N1 -1.23(17) no
C5 C6 N6 C64 -176.89(10) no
N1 C6 N6 C61 -178.70(9) no
C5 C6 N6 C61 1.53(17) y
N1 C6 N6 C64 2.88(16) y
C6 N6 C61 C62 177.59(10) no
N6 C64 C63 C62 33.10(11) y
C64 C63 C62 C61 -35.97(12) y
C63 C62 C61 N6 24.55(12) y
C62 C61 N6 C64 -3.82(13) y
C61 N6 C64 C63 -18.54(12) y
C6 N6 C64 C63 160.02(11) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4402210
