#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/99/2209926.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_2209926
loop_
_publ_author_name
'Quijano, Maria Luisa'
'Cobo, Justo'
'Nogueras, Manuel'
'Low, John Nicolson'
_publ_section_title
;
 4-Amino-6-(2,2-diethoxyethoxy)-2-(methylsulfanyl)pyrimidine
;
_journal_coeditor_code           LH2112
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3142
_journal_page_last               o3144
_journal_paper_doi               10.1107/S1600536806024536
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H19 N3 O3 S'
_chemical_formula_moiety         'C11 H19 N3 O3 S'
_chemical_formula_sum            'C11 H19 N3 O3 S'
_chemical_formula_weight         273.35
_chemical_melting_point          438
_chemical_name_systematic
;
4-amino-6-(2,2-diethoxyethoxy)-2-(methylsulfanyl)pyrimidine
;
_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
_cell_angle_alpha                81.197(9)
_cell_angle_beta                 82.390(7)
_cell_angle_gamma                78.817(8)
_cell_formula_units_Z            2
_cell_length_a                   7.2280(8)
_cell_length_b                   9.6360(9)
_cell_length_c                   10.0850(10)
_cell_measurement_reflns_used    3000
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      5.05
_cell_volume                     677.12(12)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Bruker--Nonius, 2004)'
_computing_data_reduction        'EvalCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement
'OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'Thick-slice π and ω'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1183
_diffrn_reflns_av_sigmaI/netI    0.1883
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10168
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         5.05
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.9666
_exptl_absorpt_correction_T_min  0.8835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(EvalCCD; Duisenberg et al.,  2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.530
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.2411
_refine_ls_R_factor_gt           0.0732
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1062P)²+1.0232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.2526
_reflns_number_gt                1200
_reflns_number_total             3000
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2112.cif
_cod_data_source_block           I
_cod_database_code               2209926
_cod_database_fobs_code          2209926
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N N1 0.4599(6) 0.6665(4) 0.3719(4) 0.0270(10) Uani d . 1
C C2 0.5473(7) 0.6411(5) 0.2507(5) 0.0281(12) Uani d . 1
S S2 0.7579(2) 0.70417(16) 0.19170(14) 0.0373(5) Uani d . 1
C C21 0.7992(8) 0.7871(6) 0.3302(6) 0.0401(15) Uani d . 1
N N3 0.4967(6) 0.5670(4) 0.1636(4) 0.0246(10) Uani d . 1
C C4 0.3395(7) 0.5080(5) 0.2048(5) 0.0266(12) Uani d . 1
N N4 0.2892(6) 0.4329(5) 0.1184(4) 0.0317(11) Uani d . 1
C C5 0.2369(7) 0.5264(5) 0.3319(5) 0.0278(12) Uani d . 1
C C6 0.3043(7) 0.6092(5) 0.4078(5) 0.0252(12) Uani d . 1
O O6 0.2063(5) 0.6314(4) 0.5289(3) 0.0318(9) Uani d . 1
C C61 0.2784(8) 0.7194(6) 0.6052(5) 0.0317(13) Uani d . 1
C C62 0.1616(7) 0.7193(6) 0.7414(5) 0.0307(13) Uani d . 1
O O61 0.2315(5) 0.8144(4) 0.8062(3) 0.0325(9) Uani d . 1
C C63 0.1706(9) 0.8063(6) 0.9472(5) 0.0377(14) Uani d . 1
C C64 0.2834(9) 0.8905(6) 1.0088(6) 0.0455(16) Uani d . 1
O O62 -0.0357(5) 0.7540(4) 0.7356(3) 0.0307(9) Uani d . 1
C C65 -0.1042(8) 0.8906(6) 0.6607(5) 0.0359(14) Uani d . 1
C C66 -0.3171(8) 0.9162(6) 0.6835(6) 0.0428(15) Uani d . 1
H H21A 0.9162 0.8266 0.3072 0.060 Uiso calc PR 0.50
H H21B 0.8115 0.7160 0.4106 0.060 Uiso calc PR 0.50
H H21C 0.6924 0.8640 0.3484 0.060 Uiso calc PR 0.50
H H21D 0.6972 0.7778 0.4036 0.060 Uiso calc PR 0.50
H H21E 0.8019 0.8884 0.3002 0.060 Uiso calc PR 0.50
H H21F 0.9210 0.7404 0.3624 0.060 Uiso calc PR 0.50
H H4A 0.3713 0.4190 0.0323 0.038 Uiso d R 1
H H4B 0.1858 0.3925 0.1537 0.038 Uiso d R 1
H H5 0.1280 0.4843 0.3632 0.033 Uiso calc R 1
H H61A 0.2684 0.8179 0.5574 0.038 Uiso calc R 1
H H61B 0.4135 0.6812 0.6168 0.038 Uiso calc R 1
H H62 0.1910 0.6218 0.7929 0.037 Uiso calc R 1
H H63A 0.1914 0.7056 0.9896 0.045 Uiso calc R 1
H H63B 0.0337 0.8460 0.9619 0.045 Uiso calc R 1
H H64A 0.2631 0.9896 0.9654 0.068 Uiso calc R 1
H H64B 0.4184 0.8491 0.9955 0.068 Uiso calc R 1
H H64C 0.2421 0.8878 1.1056 0.068 Uiso calc R 1
H H65A -0.0615 0.8898 0.5633 0.043 Uiso calc R 1
H H65B -0.0547 0.9672 0.6925 0.043 Uiso calc R 1
H H66A -0.3576 0.9137 0.7804 0.064 Uiso calc R 1
H H66B -0.3647 0.8419 0.6486 0.064 Uiso calc R 1
H H66C -0.3680 1.0098 0.6365 0.064 Uiso calc R 1
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.0000 '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
C6 N1 C2 114.3(4) no
N1 C2 N3 128.0(5) no
N1 C2 S2 119.7(4) no
N3 C2 S2 112.3(4) no
C2 S2 C21 102.8(3) no
S2 C21 H21A 109.5 no
S2 C21 H21B 109.5 no
H21A C21 H21B 109.5 no
S2 C21 H21C 109.5 no
H21A C21 H21C 109.5 no
H21B C21 H21C 109.5 no
S2 C21 H21D 109.5 no
H21A C21 H21D 141.1 no
H21B C21 H21D 56.3 no
H21C C21 H21D 56.3 no
S2 C21 H21E 109.5 no
H21A C21 H21E 56.3 no
H21B C21 H21E 141.1 no
H21C C21 H21E 56.3 no
H21D C21 H21E 109.5 no
S2 C21 H21F 109.5 no
H21A C21 H21F 56.3 no
H21B C21 H21F 56.3 no
H21C C21 H21F 141.1 no
H21D C21 H21F 109.5 no
H21E C21 H21F 109.5 no
C2 N3 C4 116.0(4) no
N4 C4 N3 116.2(4) no
N4 C4 C5 122.9(5) no
N3 C4 C5 120.9(4) no
C4 N4 H4A 119.3 no
C4 N4 H4B 111.8 no
H4A N4 H4B 128.5 no
C6 C5 C4 115.9(5) no
C6 C5 H5 122.1 no
C4 C5 H5 122.1 no
N1 C6 O6 117.9(4) no
N1 C6 C5 124.9(4) no
O6 C6 C5 117.2(4) no
C6 O6 C61 116.0(4) no
O6 C61 C62 107.8(4) no
O6 C61 H61A 110.1 no
C62 C61 H61A 110.1 no
O6 C61 H61B 110.1 no
C62 C61 H61B 110.1 no
H61A C61 H61B 108.5 no
O61 C62 O62 113.1(4) no
O61 C62 C61 104.5(4) no
O62 C62 C61 114.6(4) no
O61 C62 H62 108.1 no
O62 C62 H62 108.1 no
C61 C62 H62 108.1 no
C62 O61 C63 113.5(4) no
O61 C63 C64 108.1(5) no
O61 C63 H63A 110.1 no
C64 C63 H63A 110.1 no
O61 C63 H63B 110.1 no
C64 C63 H63B 110.1 no
H63A C63 H63B 108.4 no
C63 C64 H64A 109.5 no
C63 C64 H64B 109.5 no
H64A C64 H64B 109.5 no
C63 C64 H64C 109.5 no
H64A C64 H64C 109.5 no
H64B C64 H64C 109.5 no
C62 O62 C65 115.9(4) no
O62 C65 C66 107.5(4) no
O62 C65 H65A 110.2 no
C66 C65 H65A 110.2 no
O62 C65 H65B 110.2 no
C66 C65 H65B 110.2 no
H65A C65 H65B 108.5 no
C65 C66 H66A 109.5 no
C65 C66 H66B 109.5 no
H66A C66 H66B 109.5 no
C65 C66 H66C 109.5 no
H66A C66 H66C 109.5 no
H66B C66 H66C 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 1.331(6) no
N1 C2 1.335(6) no
C2 N3 1.339(6) no
C2 S2 1.746(5) no
S2 C21 1.796(5) no
C21 H21A 0.98 no
C21 H21B 0.98 no
C21 H21C 0.98 no
C21 H21D 0.98 no
C21 H21E 0.98 no
C21 H21F 0.98 no
N3 C4 1.357(6) no
C4 N4 1.340(6) no
C4 C5 1.411(7) no
N4 H4A 0.9959 no
N4 H4B 0.9151 no
C5 C6 1.377(7) no
C5 H5 0.95 no
C6 O6 1.354(6) no
O6 C61 1.435(6) no
C61 C62 1.514(7) no
C61 H61A 0.99 no
C61 H61B 0.99 no
C62 O61 1.404(6) no
C62 O62 1.407(6) no
C62 H62 1.00 no
O61 C63 1.427(6) no
C63 C64 1.501(7) no
C63 H63A 0.99 no
C63 H63B 0.99 no
C64 H64A 0.98 no
C64 H64B 0.98 no
C64 H64C 0.98 no
O62 C65 1.446(6) no
C65 C66 1.503(8) no
C65 H65A 0.99 no
C65 H65B 0.99 no
C66 H66A 0.98 no
C66 H66B 0.98 no
C66 H66C 0.98 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
N4 H4A N3 2_665 1.00 2.07 3.052(6) 167 y
N4 H4B O62 2_566 0.91 2.05 2.919(6) 158 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 0.3(7) no
C6 N1 C2 S2 -177.9(3) no
N1 C2 S2 C21 2.1(5) no
N3 C2 S2 C21 -176.3(4) no
N1 C2 N3 C4 -1.5(7) no
S2 C2 N3 C4 176.8(3) no
C2 N3 C4 N4 -179.6(4) no
C2 N3 C4 C5 0.6(7) no
N4 C4 C5 C6 -178.5(5) no
N3 C4 C5 C6 1.3(7) no
C2 N1 C6 O6 -179.3(4) no
C2 N1 C6 C5 2.0(7) no
C4 C5 C6 N1 -2.7(7) no
C4 C5 C6 O6 178.6(4) no
N1 C6 O6 C61 1.9(6) no
C5 C6 O6 C61 -179.3(4) no
C6 O6 C61 C62 -174.7(4) no
O6 C61 C62 O61 -176.2(4) no
O6 C61 C62 O62 -51.8(6) no
O62 C62 O61 C63 68.0(5) no
C61 C62 O61 C63 -166.7(4) no
C62 O61 C63 C64 169.2(4) no
O61 C62 O62 C65 62.1(5) no
C61 C62 O62 C65 -57.5(6) no
C62 O62 C65 C66 -171.9(4) no
