#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/02/2010205.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_2010205
loop_
_publ_author_name
'Sinur, Amalija'
'Goli\<c, Ljubo'
'Stanovnik, Branko'
_publ_section_title
;
 Three substituted 3-aminopropenoates
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1842
_journal_page_last               1846
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C13 H18 N4 O3 S'
_chemical_formula_sum            'C13 H18 N4 O3 S'
_chemical_formula_weight         310.4
_chemical_name_systematic
;
Methyl (Z)-3-(4,6-dimethylpyrimidinyl-2)amino-2-(1-methoxy-
-1-methylthio)methyleneaminopropenoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           from_xtal_archive_file_using_CIFIO
_cell_angle_alpha                71.904(7)
_cell_angle_beta                 88.558(7)
_cell_angle_gamma                81.614(8)
_cell_formula_units_Z            2
_cell_length_a                   8.3383(7)
_cell_length_b                   9.4365(7)
_cell_length_c                   10.5925(8)
_cell_measurement_reflns_used    75
_cell_measurement_temperature    293
_cell_measurement_theta_max      15.790
_cell_measurement_theta_min      9.965
_cell_volume                     783.59(11)
_computing_cell_refinement       xray_PARAM
_computing_data_collection       'Enraf-Nonius CAD-4'
_computing_data_reduction        xtal_DIFDAT_SORTRF_ADDREF
_computing_publication_material  xtal_CIFIO
_computing_structure_refinement  xtal_CRYLSQ
_computing_structure_solution    MULTAN88
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         xray_tube
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .011
_diffrn_reflns_av_sigmaI/netI    .014
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9131
_diffrn_reflns_theta_max         29.92
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        -.23
_diffrn_standards_interval_count '500 (orientation)'
_diffrn_standards_interval_time  '333 (intensity)'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .2111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      1.31
_exptl_crystal_description       irregular
_exptl_crystal_F_000             328
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .52
_exptl_crystal_size_min          .32
_refine_diff_density_max         .445
_refine_diff_density_min         -.420
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   0
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   .983
_refine_ls_goodness_of_fit_obs   1.019
_refine_ls_hydrogen_treatment    refxyzUiso
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3852
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .06
_refine_ls_R_factor_obs          .042
_refine_ls_shift/esd_max         .069
_refine_ls_shift/esd_mean        .003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme
;
calc w = 6*w~f~*w~s~
where
 w~f~ = (|F~o~|/2.59)^1.2^ for |F~o~| < 2.59
 w~f~ = (7.77/|F~o~|)^1.4^ for |F~o~| > 7.77
 w~f~ = 1.0  for  2.59 <= |F~o~| <= 7.77
 w~s~ = (sin\q/0.4)^1.9^  for sin\q < 0.4
 w~s~ = 1.0 for sin\q >= 0.4
;
_refine_ls_wR_factor_all         .058
_refine_ls_wR_factor_obs         .044
_reflns_number_observed          3269
_reflns_number_total             4540
_reflns_observed_criterion       Inet>2.5\s(Inet)
_[local]_cod_data_source_file    ka1064.cif
_[local]_cod_data_source_block   NOV
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_site_thermal_displace_type' tag value 'Uij' was replaced with
'Uani' value 21 time.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        783.6(2)
_cod_database_code               2010205
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,-y,-z
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
_atom_site_aniso_type_symbol
S .0553(2) .0631(3) .0552(2) -.02108(18) .00653(17) -.02731(19) S
O(1) .0552(6) .0470(6) .0627(7) .0140(5) .0065(5) -.0186(5) O
O(2) .0500(6) .0448(6) .0735(8) -.0037(5) .0098(5) -.0110(5) O
O(3) .0408(5) .0488(5) .0502(6) -.0089(4) .0068(4) -.0205(4) O
N(1) .0381(6) .0390(6) .0621(8) .0029(5) .0142(6) -.0179(6) N
N(2) .0358(5) .0493(7) .0521(7) .0029(5) .0043(5) -.0228(5) N
N(3) .0459(7) .0407(6) .0653(8) .0051(5) .0049(6) -.0199(6) N
N(4) .0372(5) .0410(6) .0533(7) .0004(4) .0054(5) -.0225(5) N
C(1) .0458(7) .0402(7) .0458(7) .0028(5) .0033(6) -.0189(6) C
C(2) .0385(6) .0399(7) .0483(7) .0008(5) .0060(5) -.0201(6) C
C(3) .0381(6) .0389(6) .0514(8) .0017(5) .0069(6) -.0191(6) C
C(4) .0351(6) .0418(7) .0507(7) .0043(5) .0013(5) -.0210(6) C
C(5) .0344(6) .0624(9) .0539(8) .0060(6) .0008(6) -.0300(7) C
C(6) .0415(7) .0612(10) .0698(10) .0161(7) -.0026(7) -.0366(8) C
C(7) .0498(8) .0453(8) .0678(10) .0118(6) -.0074(7) -.0253(7) C
C(8) .0465(9) .0851(14) .0689(12) -.0006(9) .0164(8) -.0314(11) C
C(9) .0950(18) .0430(10) .1031(19) .0139(11) -.0057(15) -.0257(11) C
C(10) .0351(6) .0332(6) .0469(7) .0012(5) .0014(5) -.0146(5) C
C(11) .0475(8) .0543(9) .0640(10) -.0145(7) .0001(7) -.0210(8) C
C(12) .0649(11) .0708(12) .0536(9) -.0135(9) .0042(8) -.0310(9) C
C(13) .0767(14) .0487(10) .0759(14) -.0112(9) .0009(11) -.0028(9) C
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
S 0.58045(5) 0.29674(5) 0.48459(4) 0.05460(16) Uani ? ? S
O(1) 0.51682(15) 0.50181(13) 0.15432(13) 0.0569(4) Uani ? ? O
O(2) 0.77469(15) 0.46254(13) 0.09288(14) 0.0583(4) Uani ? ? O
O(3) 0.34026(12) 0.16263(12) 0.45193(11) 0.0452(4) Uani ? ? O
N(1) 0.82096(16) 0.01051(14) 0.27280(14) 0.0470(4) Uani ? ? N
N(2) 1.06423(14) -0.02181(15) 0.16832(13) 0.0451(4) Uani ? ? N
N(3) 0.93867(16) -0.23225(15) 0.29666(15) 0.0511(5) Uani ? ? N
N(4) 0.52197(14) 0.19147(14) 0.28424(13) 0.0427(4) Uani ? ? N
C(1) 0.64018(18) 0.41690(16) 0.15512(15) 0.0436(5) Uani ? ? C
C(2) 0.66017(17) 0.25336(16) 0.22362(15) 0.0415(4) Uani ? ? C
C(3) 0.79865(17) 0.16413(16) 0.21435(15) 0.0425(5) Uani ? ? C
C(4) 0.94890(16) -0.08561(16) 0.24432(15) 0.0421(4) Uani ? ? C
C(5) 1.18296(17) -0.1179(2) 0.13798(16) 0.0488(5) Uani ? ? C
C(6) 1.1818(2) -0.2709(2) 0.18263(19) 0.0561(6) Uani ? ? C
C(7) 1.0584(2) -0.32594(19) 0.26416(19) 0.0543(6) Uani ? ? C
C(8) 1.3163(2) -0.0485(3) 0.0557(2) 0.0663(8) Uani ? ? C
C(9) 1.0491(4) -0.4918(2) 0.3198(4) 0.0820(11) Uani ? ? C
C(10) 0.47560(16) 0.20988(14) 0.39349(14) 0.0385(4) Uani ? ? C
C(11) 0.2369(2) 0.1096(2) 0.3745(2) 0.0539(6) Uani ? ? C
C(12) 0.4580(3) 0.2858(3) 0.62774(19) 0.0601(7) Uani ? ? C
C(13) 0.7637(3) 0.6212(2) 0.0240(3) 0.0707(8) Uani ? ? C
H(1) 0.750(3) -0.031(2) 0.317(2) 0.045(5) Uiso ? ? H
H(3) 0.886(2) 0.205(2) 0.1639(19) 0.046(4) Uiso ? ? H
H(6) 1.263(3) -0.333(3) 0.158(3) 0.074(7) Uiso ? ? H
H(81) 1.392(5) -0.121(5) 0.029(4) 0.129(12) Uiso ? ? H
H(82) 1.276(4) 0.023(3) -0.025(3) 0.085(8) Uiso ? ? H
H(83) 1.370(4) 0.005(3) 0.101(3) 0.091(8) Uiso ? ? H
H(91) 1.068(6) -0.540(6) 0.256(6) 0.160(17) Uiso ? ? H
H(92) 1.109(6) -0.524(5) 0.380(5) 0.135(16) Uiso ? ? H
H(93) 0.937(7) -0.513(6) 0.331(5) 0.156(17) Uiso ? ? H
H(111) 0.212(3) 0.183(3) 0.287(3) 0.077(7) Uiso ? ? H
H(112) 0.143(4) 0.103(3) 0.421(3) 0.079(7) Uiso ? ? H
H(113) 0.289(4) 0.016(4) 0.364(3) 0.093(8) Uiso ? ? H
H(121) 0.498(3) 0.348(3) 0.664(3) 0.079(7) Uiso ? ? H
H(122) 0.472(3) 0.173(3) 0.691(3) 0.082(7) Uiso ? ? H
H(123) 0.347(4) 0.322(3) 0.601(3) 0.077(7) Uiso ? ? H
H(131) 0.684(4) 0.654(4) -0.042(4) 0.101(10) Uiso ? ? H
H(132) 0.733(4) 0.677(4) 0.091(4) 0.105(10) Uiso ? ? H
H(133) 0.868(5) 0.635(4) 0.000(3) 0.103(10) Uiso ? ? H
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S C(10) . . 1.764(2) yes
S C(12) . . 1.791(2) yes
O(1) C(1) . . 1.207(2) yes
O(2) C(1) . . 1.344(2) yes
O(2) C(13) . . 1.438(2) yes
O(3) C(10) . . 1.340(2) yes
O(3) C(11) . . 1.444(3) yes
N(1) C(3) . . 1.374(2) yes
N(1) C(4) . . 1.387(2) yes
N(1) H(1) . . .82(2) no
N(2) C(4) . . 1.328(2) yes
N(2) C(5) . . 1.345(2) yes
N(3) C(4) . . 1.336(2) yes
N(3) C(7) . . 1.346(2) yes
N(4) C(2) . . 1.417(2) yes
N(4) C(10) . . 1.266(2) yes
C(1) C(2) . . 1.474(2) yes
C(2) C(3) . . 1.347(2) yes
C(3) H(3) . . .95(2) no
C(5) C(6) . . 1.374(3) yes
C(5) C(8) . . 1.494(3) yes
C(6) C(7) . . 1.381(2) yes
C(6) H(6) . . .92(3) no
C(7) C(9) . . 1.504(3) yes
C(8) H(81) . . .96(5) no
C(8) H(82) . . .94(3) no
C(8) H(83) . . .96(4) no
C(9) H(91) . . .92(7) no
C(9) H(92) . . .78(5) no
C(9) H(93) . . .98(6) no
C(11) H(111) . . .97(3) no
C(11) H(112) . . .92(3) no
C(11) H(113) . . .96(3) no
C(12) H(121) . . .90(3) no
C(12) H(122) . . 1.06(3) no
C(12) H(123) . . .96(3) no
C(13) H(131) . . .92(4) no
C(13) H(132) . . 1.02(4) no
C(13) H(133) . . .92(4) no
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .002 .002 International_Tables_Vol_IV_Table_2.2B
H 0 0 International_Tables_Vol_IV_Table_2.2B
O .008 .006 International_Tables_Vol_IV_Table_2.2B
N .004 .003 International_Tables_Vol_IV_Table_2.2B
S .11 .124 International_Tables_Vol_IV_Table_2.2B
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -4 1
5 -1 2
3 3 3
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
C(10) S C(12) 103.10(10) yes
C(1) O(2) C(13) 115.7(2) yes
C(10) O(3) C(11) 116.20(10) yes
C(3) N(1) C(4) 123.50(10) yes
C(3) N(1) H(1) 120.0(10) no
C(4) N(1) H(1) 115.0(10) no
C(4) N(2) C(5) 115.30(10) yes
C(4) N(3) C(7) 115.30(10) yes
C(2) N(4) C(10) 119.20(10) yes
O(1) C(1) O(2) 123.10(10) yes
O(1) C(1) C(2) 124.10(10) yes
O(2) C(1) C(2) 112.80(10) yes
N(4) C(2) C(1) 117.50(10) yes
N(4) C(2) C(3) 121.20(10) yes
C(1) C(2) C(3) 120.90(10) yes
N(1) C(3) C(2) 123.00(10) yes
N(1) C(3) H(3) 116.0(10) no
C(2) C(3) H(3) 121.0(10) no
N(1) C(4) N(2) 116.80(10) yes
N(1) C(4) N(3) 115.00(10) yes
N(2) C(4) N(3) 128.20(10) yes
N(2) C(5) C(6) 121.40(10) yes
N(2) C(5) C(8) 116.1(2) yes
C(6) C(5) C(8) 122.5(2) yes
C(5) C(6) C(7) 118.6(2) yes
C(5) C(6) H(6) 119(2) no
C(7) C(6) H(6) 122(2) no
N(3) C(7) C(6) 121.1(2) yes
N(3) C(7) C(9) 116.6(2) yes
C(6) C(7) C(9) 122.3(2) yes
C(5) C(8) H(81) 113(3) no
C(5) C(8) H(82) 112(2) no
C(5) C(8) H(83) 110(2) no
H(81) C(8) H(82) 104(3) no
H(81) C(8) H(83) 112(3) no
H(82) C(8) H(83) 106(3) no
C(7) C(9) H(91) 112(3) no
C(7) C(9) H(92) 107(4) no
C(7) C(9) H(93) 112(3) no
H(91) C(9) H(92) 114(5) no
H(91) C(9) H(93) 93(5) no
H(92) C(9) H(93) 119(5) no
S C(10) O(3) 113.30(10) yes
S C(10) N(4) 124.40(10) yes
O(3) C(10) N(4) 122.30(10) yes
O(3) C(11) H(111) 111(2) no
O(3) C(11) H(112) 103(2) no
O(3) C(11) H(113) 110(2) no
H(111) C(11) H(112) 108(2) no
H(111) C(11) H(113) 109(3) no
H(112) C(11) H(113) 115(3) no
S C(12) H(121) 103(2) no
S C(12) H(122) 109(2) no
S C(12) H(123) 110(2) no
H(121) C(12) H(122) 113(2) no
H(121) C(12) H(123) 111(3) no
H(122) C(12) H(123) 111(2) no
O(2) C(13) H(131) 112(2) no
O(2) C(13) H(132) 108(2) no
O(2) C(13) H(133) 104(2) no
H(131) C(13) H(132) 107(3) no
H(131) C(13) H(133) 118(3) no
H(132) C(13) H(133) 107(3) 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
_geom_torsion_publ_flag
C(12) S C(10) O(3) .30(10) no
C(12) S C(10) N(4) -179.10(10) no
C(10) S C(12) H(121) -168(2) no
C(10) S C(12) H(122) 72(2) no
C(10) S C(12) H(123) -50(2) no
C(13) O(2) C(1) O(1) .1(3) no
C(13) O(2) C(1) C(2) -179.9(2) no
C(1) O(2) C(13) H(131) -60(3) no
C(1) O(2) C(13) H(132) 58(2) no
C(1) O(2) C(13) H(133) 171(3) no
C(11) O(3) C(10) S 171.70(10) no
C(11) O(3) C(10) N(4) -8.9(2) no
C(10) O(3) C(11) H(111) -52(2) no
C(10) O(3) C(11) H(112) -167(2) no
C(10) O(3) C(11) H(113) 70(2) no
C(4) N(1) C(3) C(2) 167.5(2) no
C(4) N(1) C(3) H(3) -11.0(10) no
H(1) N(1) C(3) C(2) -1(2) no
H(1) N(1) C(3) H(3) -180(2) no
C(3) N(1) C(4) N(2) 8.1(2) no
C(3) N(1) C(4) N(3) -171.2(2) no
H(1) N(1) C(4) N(2) 178(2) no
H(1) N(1) C(4) N(3) -2(2) no
C(5) N(2) C(4) N(1) -177.30(10) no
C(5) N(2) C(4) N(3) 1.9(3) no
C(4) N(2) C(5) C(6) .6(2) no
C(4) N(2) C(5) C(8) -178.4(2) no
C(7) N(3) C(4) N(1) 176.9(2) no
C(7) N(3) C(4) N(2) -2.3(3) no
C(4) N(3) C(7) C(6) .3(3) no
C(4) N(3) C(7) C(9) -179.1(2) no
C(10) N(4) C(2) C(1) -76.4(2) no
C(10) N(4) C(2) C(3) 111.8(2) no
C(2) N(4) C(10) S -5.0(2) no
C(2) N(4) C(10) O(3) 175.70(10) no
O(1) C(1) C(2) N(4) 4.6(3) no
O(1) C(1) C(2) C(3) 176.4(2) no
O(2) C(1) C(2) N(4) -175.40(10) no
O(2) C(1) C(2) C(3) -3.6(2) no
N(4) C(2) C(3) N(1) -6.3(3) no
N(4) C(2) C(3) H(3) 172(2) no
C(1) C(2) C(3) N(1) -177.8(2) no
C(1) C(2) C(3) H(3) 0(2) no
N(2) C(5) C(6) C(7) -2.3(3) no
N(2) C(5) C(6) H(6) 178(2) no
C(8) C(5) C(6) C(7) 176.6(2) no
C(8) C(5) C(6) H(6) -3(2) no
N(2) C(5) C(8) H(81) -174(3) no
N(2) C(5) C(8) H(82) -57(2) no
N(2) C(5) C(8) H(83) 61(2) no
C(6) C(5) C(8) H(81) 7(3) no
C(6) C(5) C(8) H(82) 124(2) no
C(6) C(5) C(8) H(83) -118.2(2) no
C(5) C(6) C(7) N(3) 1.9(3) no
C(5) C(6) C(7) C(9) -178.8(2) no
H(6) C(6) C(7) N(3) -179(2) no
H(6) C(6) C(7) C(9) 0(2) no
N(3) C(7) C(9) H(91) 134(4) no
N(3) C(7) C(9) H(92) -101(4) no
N(3) C(7) C(9) H(93) 31(4) no
C(6) C(7) C(9) H(91) -45(4) no
C(6) C(7) C(9) H(92) 80(4) no
C(6) C(7) C(9) H(93) -148(4) no
_journal_paper_doi 10.1107/S0108270193013423