#------------------------------------------------------------------------------
#$Date: 2013-03-09 18:03:10 +0200 (Sat, 09 Mar 2013) $
#$Revision: 75295 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/72/2237295.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_2237295
loop_
_publ_author_name
'Draguta, Sergiu'
'Sandhu, Bhupinder'
'Khrustalev, Victor N.'
'Fonari, Marina S.'
'Timofeeva, Tatiana V.'
_publ_section_title
;
Pyrimidine-2,4-diamine acetone monosolvate
;
_journal_coeditor_code CV5381
_journal_issue 2
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o251
_journal_volume 69
_journal_year 2013
_chemical_formula_iupac 'C4 H6 N4, C3 H6 O'
_chemical_formula_moiety 'C4 H6 N4, C3 H6 O'
_chemical_formula_sum 'C7 H12 N4 O'
_chemical_formula_weight 168.21
_chemical_name_common '2,4-diaminopyrimidine acetone monosolvate'
_chemical_name_systematic
;
Pyrimidine-2,4-diamine acetone monosolvate
;
_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 difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 99.395(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 8.1594(15)
_cell_length_b 12.728(2)
_cell_length_c 8.7663(16)
_cell_measurement_reflns_used 8851
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 32.08
_cell_measurement_theta_min 2.29
_cell_volume 898.2(3)
_computing_cell_refinement 'SAINT (Bruker, 2001)'
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_data_reduction 'SAINT (Bruker, 2001)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature 296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker APEXII CCD'
_diffrn_measurement_method '\f and \w 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 0.0512
_diffrn_reflns_av_sigmaI/netI 0.0389
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_number 9693
_diffrn_reflns_theta_full 28.00
_diffrn_reflns_theta_max 28.00
_diffrn_reflns_theta_min 2.53
_exptl_absorpt_coefficient_mu 0.089
_exptl_absorpt_correction_T_max 0.982
_exptl_absorpt_correction_T_min 0.974
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.244
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism
_exptl_crystal_F_000 360
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.20
_refine_diff_density_max 0.281
_refine_diff_density_min -0.276
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.066
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 127
_refine_ls_number_reflns 2170
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.066
_refine_ls_R_factor_all 0.0602
_refine_ls_R_factor_gt 0.0478
_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/[\s^2^(Fo^2^)+(0.0884P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1325
_refine_ls_wR_factor_ref 0.1390
_reflns_number_gt 1752
_reflns_number_total 2170
_reflns_threshold_expression I>2\s(I)
_journal_paper_doi 10.1107/S1600536813001025
_iucr_refine_instructions_details
;
TITL I in P2(1)/c
CELL 0.71073 8.1594 12.7284 8.7663 90.000 99.395 90.000
ZERR 4.00 0.0015 0.0023 0.0016 0.000 0.003 0.000
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 28 48 16 4
TEMP 23.0
SIZE 0.20 0.25 0.30
OMIT -0 56
L.S. 6
BOND $H
ACTA
CONF
HTAB
WGHT 0.088400
FVAR 0.14180
N1 3 0.123009 0.395542 0.118475 11.00000 0.02486 0.01681 =
0.02264 -0.00205 -0.00455 -0.00118
C2 1 0.196643 0.474896 0.206576 11.00000 0.02032 0.01617 =
0.01992 -0.00090 0.00028 -0.00069
N2 3 0.142767 0.573094 0.167440 11.00000 0.03041 0.01531 =
0.02600 0.00031 -0.00930 -0.00012
H2A 2 0.069087 0.583829 0.085214 11.00000 0.02505
H2B 2 0.197022 0.624903 0.218259 11.00000 0.03338
N3 3 0.316910 0.465303 0.332128 11.00000 0.02091 0.01249 =
0.02122 0.00009 -0.00116 -0.00029
C4 1 0.367275 0.367282 0.374831 11.00000 0.01902 0.01550 =
0.02168 0.00027 0.00063 -0.00014
N4 3 0.486498 0.357012 0.499033 11.00000 0.02554 0.01342 =
0.02877 0.00117 -0.00797 0.00075
H4A 2 0.523728 0.294394 0.529441 11.00000 0.03318
H4B 2 0.539123 0.412017 0.549766 11.00000 0.03061
C5 1 0.296274 0.279034 0.290981 11.00000 0.02705 0.01385 =
0.03029 -0.00113 -0.00253 0.00066
AFIX 43
H5 2 0.328298 0.210867 0.320206 11.00000 -1.20000
AFIX 0
C6 1 0.178396 0.298913 0.165018 11.00000 0.02794 0.01620 =
0.02769 -0.00463 -0.00270 -0.00124
AFIX 43
H6 2 0.132871 0.241731 0.106976 11.00000 -1.20000
AFIX 0
O1 4 0.285153 0.783744 0.308844 11.00000 0.03251 0.01835 =
0.03144 0.00369 -0.00421 0.00240
C7 1 0.300856 0.970137 0.316312 11.00000 0.03757 0.02098 =
0.04245 -0.00663 0.00989 -0.00526
AFIX 137
H7A 2 0.369903 0.958312 0.414424 11.00000 -1.50000
H7B 2 0.206727 1.011974 0.330838 11.00000 -1.50000
H7C 2 0.363499 1.006338 0.248883 11.00000 -1.50000
AFIX 0
C8 1 0.242375 0.867044 0.245917 11.00000 0.02167 0.01820 =
0.02678 0.00140 0.00286 0.00068
C9 1 0.126603 0.869317 0.093509 11.00000 0.02709 0.03110 =
0.02892 0.00589 -0.00173 0.00320
AFIX 137
H9A 2 0.131605 0.803191 0.041800 11.00000 -1.50000
H9B 2 0.159228 0.924630 0.030312 11.00000 -1.50000
H9C 2 0.015148 0.881580 0.111221 11.00000 -1.50000
HKLF 4
REM I in P2(1)/c
REM R1 = 0.0478 for 1752 Fo > 4sig(Fo) and 0.0602 for all 2170 data
REM 127 parameters refined using 0 restraints
END
WGHT 0.0884 0.0000
REM Highest difference peak 0.281, deepest hole -0.276, 1-sigma level 0.056
Q1 1 0.0466 0.3955 0.0531 11.00000 0.05 0.28
Q2 1 0.4142 0.3622 0.4423 11.00000 0.05 0.28
Q3 1 0.1962 0.8692 0.1672 11.00000 0.05 0.27
Q4 1 0.2574 0.4688 0.2714 11.00000 0.05 0.22
Q5 1 0.2471 0.2913 0.2292 11.00000 0.05 0.22
Q6 1 0.3313 0.3199 0.3383 11.00000 0.05 0.21
Q7 1 0.4209 0.9764 0.3216 11.00000 0.05 0.19
Q8 1 0.3961 0.7846 0.2952 11.00000 0.05 0.19
Q9 1 0.4004 0.9681 0.3537 11.00000 0.05 0.18
Q10 1 0.4090 0.3574 0.5709 11.00000 0.05 0.17
Q11 1 0.2755 0.9801 0.4235 11.00000 0.05 0.15
Q12 1 0.3769 0.7883 0.3698 11.00000 0.05 0.15
Q13 1 0.0289 0.9394 0.1104 11.00000 0.05 0.15
Q14 1 0.5901 0.3514 0.4276 11.00000 0.05 0.15
Q15 1 0.0230 0.3862 0.1767 11.00000 0.05 0.14
Q16 1 0.3301 0.4763 0.2214 11.00000 0.05 0.14
Q17 1 0.0252 0.5794 0.1785 11.00000 0.05 0.13
Q18 1 0.3413 0.4166 0.3454 11.00000 0.05 0.13
Q19 1 0.1721 0.8795 0.0000 11.00000 0.05 0.13
Q20 1 0.2715 0.9211 0.2799 11.00000 0.05 0.13
;
_[local]_cod_data_source_file cv5381.cif
_[local]_cod_data_source_block I
_[local]_cod_cif_authors_sg_H-M 'P 21/c'
_cod_database_code 2237295
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
_atom_site_symmetry_multiplicity
N N1 0.12301(13) 0.39554(8) 0.11848(12) 0.0224(3) Uani d . 1 1
C C2 0.19664(15) 0.47490(9) 0.20658(14) 0.0191(3) Uani d . 1 1
N N2 0.14277(14) 0.57309(9) 0.16744(13) 0.0255(3) Uani d . 1 1
H H2A 0.0691(19) 0.5838(13) 0.0852(18) 0.025(4) Uiso d . 1 1
H H2B 0.197(2) 0.6249(13) 0.2183(19) 0.033(4) Uiso d . 1 1
N N3 0.31691(12) 0.46530(8) 0.33213(12) 0.0187(3) Uani d . 1 1
C C4 0.36727(15) 0.36728(9) 0.37483(14) 0.0190(3) Uani d . 1 1
N N4 0.48650(14) 0.35701(8) 0.49903(13) 0.0240(3) Uani d . 1 1
H H4A 0.5237(19) 0.2944(14) 0.5294(18) 0.033(4) Uiso d . 1 1
H H4B 0.539(2) 0.4120(14) 0.5498(19) 0.031(4) Uiso d . 1 1
C C5 0.29627(16) 0.27903(10) 0.29098(15) 0.0245(3) Uani d . 1 1
H H5 0.3283 0.2109 0.3202 0.029 Uiso calc R 1 1
C C6 0.17840(16) 0.29891(10) 0.16502(15) 0.0248(3) Uani d . 1 1
H H6 0.1329 0.2417 0.1070 0.030 Uiso calc R 1 1
O O1 0.28515(12) 0.78374(7) 0.30884(11) 0.0285(3) Uani d . 1 1
C C7 0.30086(19) 0.97014(11) 0.31631(19) 0.0333(4) Uani d . 1 1
H H7A 0.3699 0.9583 0.4144 0.050 Uiso calc R 1 1
H H7B 0.2067 1.0120 0.3308 0.050 Uiso calc R 1 1
H H7C 0.3635 1.0063 0.2489 0.050 Uiso calc R 1 1
C C8 0.24238(15) 0.86704(9) 0.24592(14) 0.0223(3) Uani d . 1 1
C C9 0.12660(17) 0.86932(11) 0.09351(16) 0.0297(3) Uani d . 1 1
H H9A 0.1316 0.8032 0.0418 0.045 Uiso calc R 1 1
H H9B 0.1592 0.9246 0.0303 0.045 Uiso calc R 1 1
H H9C 0.0151 0.8816 0.1112 0.045 Uiso calc R 1 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
N1 0.0249(6) 0.0168(5) 0.0226(5) -0.0012(4) -0.0046(4) -0.0021(4)
C2 0.0203(6) 0.0162(6) 0.0199(6) -0.0007(4) 0.0003(5) -0.0009(4)
N2 0.0304(6) 0.0153(6) 0.0260(6) -0.0001(4) -0.0093(5) 0.0003(4)
N3 0.0209(5) 0.0125(5) 0.0212(5) -0.0003(4) -0.0012(4) 0.0001(4)
C4 0.0190(6) 0.0155(6) 0.0217(6) -0.0001(4) 0.0006(4) 0.0003(4)
N4 0.0255(6) 0.0134(5) 0.0288(6) 0.0008(4) -0.0080(4) 0.0012(4)
C5 0.0270(7) 0.0138(6) 0.0303(7) 0.0007(5) -0.0025(5) -0.0011(5)
C6 0.0279(7) 0.0162(6) 0.0277(6) -0.0012(5) -0.0027(5) -0.0046(5)
O1 0.0325(5) 0.0184(5) 0.0314(5) 0.0024(4) -0.0042(4) 0.0037(4)
C7 0.0376(8) 0.0210(7) 0.0424(8) -0.0053(6) 0.0099(6) -0.0066(6)
C8 0.0217(6) 0.0182(6) 0.0268(6) 0.0007(5) 0.0029(5) 0.0014(5)
C9 0.0271(7) 0.0311(7) 0.0289(7) 0.0032(5) -0.0017(5) 0.0059(5)
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
C6 N1 C2 114.36(11)
N2 C2 N1 116.78(11)
N2 C2 N3 116.88(11)
N1 C2 N3 126.32(11)
C2 N2 H2A 120.5(11)
C2 N2 H2B 116.9(11)
H2A N2 H2B 121.8(15)
C4 N3 C2 117.17(10)
N4 C4 N3 117.59(11)
N4 C4 C5 121.69(11)
N3 C4 C5 120.71(11)
C4 N4 H4A 120.2(11)
C4 N4 H4B 123.3(10)
H4A N4 H4B 116.2(15)
C6 C5 C4 116.64(12)
C6 C5 H5 121.7
C4 C5 H5 121.7
N1 C6 C5 124.78(11)
N1 C6 H6 117.6
C5 C6 H6 117.6
C8 C7 H7A 109.5
C8 C7 H7B 109.5
H7A C7 H7B 109.5
C8 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O1 C8 C7 121.87(12)
O1 C8 C9 120.66(11)
C7 C8 C9 117.47(12)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.3503(16)
N1 C2 1.3513(16)
C2 N2 1.3505(16)
C2 N3 1.3552(16)
N2 H2A 0.871(16)
N2 H2B 0.875(18)
N3 C4 1.3474(15)
C4 N4 1.3428(16)
C4 C5 1.4137(17)
N4 H4A 0.879(17)
N4 H4B 0.900(18)
C5 C6 1.3644(18)
C5 H5 0.9300
C6 H6 0.9300
O1 C8 1.2196(15)
C7 C8 1.4948(18)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 C9 1.5054(18)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
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 0.875(18) 2.191(18) 3.0608(18) 177.3(15) yes
N2 H2B O1 . 0.871(16) 2.247(19) 3.0990(17) 164.7(16) yes
N4 H4A O1 3_666 0.879(17) 2.170(18) 2.9141(16) 142.2(15) yes
N4 H4B N3 3_666 0.900(18) 2.120(19) 3.0171(17) 174.9(15) yes
C9 H9C Cg 2_555 0.96 2.63 3.5484(17) 159 yes
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
C6 N1 C2 N2 -178.34(11)
C6 N1 C2 N3 0.25(19)
N2 C2 N3 C4 177.85(11)
N1 C2 N3 C4 -0.75(19)
C2 N3 C4 N4 179.95(11)
C2 N3 C4 C5 -0.04(18)
N4 C4 C5 C6 -178.77(12)
N3 C4 C5 C6 1.21(19)
C2 N1 C6 C5 1.10(19)
C4 C5 C6 N1 -1.8(2)