#------------------------------------------------------------------------------
#$Date: 2018-04-30 20:05:30 +0300 (Mon, 30 Apr 2018) $
#$Revision: 207579 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/93/1549348.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_1549348
loop_
_publ_author_name
'Choudhury, Manisha'
'Viswanathan, Vijayan'
'Timiri, Ajay Kumar'
'Sinha, Barij Nayan'
'Jeyaprakash, Venkatesan'
'Velmurugan, Devadasan'
_publ_section_title
;
 2-[(4,6-Diaminopyrimidin-2-yl)sulfanyl]-N-(4-methoxyphenyl)acetamide
;
_journal_coeditor_code           IS4027
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x180600
_journal_paper_doi               10.1107/S2414314618006004
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'C13 H15 N5 O2 S'
_chemical_formula_moiety         'C13 H15 N5 O2 S'
_chemical_formula_sum            'C13 H15 N5 O2 S'
_chemical_formula_weight         305.36
_chemical_name_systematic
;
2-[(4,6-Diaminopyrimidin-2-yl)sulfanyl]-N-(4-methoxyphenyl)acetamide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.2763(6)
_cell_length_b                   7.5909(2)
_cell_length_c                   20.0571(6)
_cell_measurement_reflns_used    3471
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.342
_cell_measurement_theta_min      2.031
_cell_volume                     2782.59(14)
_computing_cell_refinement
;
APEX2 (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2015)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14130
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_min         2.031
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.823
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.273
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0417
_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)+(0.0494P)²+0.2859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                2119
_reflns_number_total             3471
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            is4027sup1.cif
_cod_data_source_block           I
_cod_database_code               1549348
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.930
_shelx_estimated_absorpt_t_max   0.953
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_occupancy
H H1D -0.0645(12) 0.581(3) 0.0150(12) 0.064(7) Uiso d 1
H H1E -0.1267(12) 0.591(3) 0.0632(11) 0.052(7) Uiso d 1
H H2A -0.0275(12) 0.190(3) 0.2877(11) 0.048(7) Uiso d 1
H H2B -0.1027(12) 0.269(3) 0.2704(10) 0.045(6) Uiso d 1
H H5 0.1243(11) 0.295(3) 0.2612(9) 0.042(6) Uiso d 1
C C1 0.11212(15) 0.6519(4) 0.56365(12) 0.0726(8) Uani d 1
H H1A 0.1009 0.7542 0.5375 0.109 Uiso calc 1
H H1B 0.1226 0.6868 0.6086 0.109 Uiso calc 1
H H1C 0.0710 0.5731 0.5634 0.109 Uiso calc 1
C C2 0.16810(11) 0.5039(3) 0.47250(9) 0.0387(5) Uani d 1
C C3 0.22722(11) 0.4076(3) 0.44951(9) 0.0399(5) Uani d 1
H H3 0.2665 0.3864 0.4778 0.048 Uiso calc 1
C C4 0.22885(10) 0.3426(3) 0.38539(9) 0.0375(5) Uani d 1
H H4 0.2690 0.2781 0.3707 0.045 Uiso calc 1
C C5 0.17026(10) 0.3739(3) 0.34272(9) 0.0337(5) Uani d 1
C C6 0.11077(10) 0.4671(3) 0.36636(10) 0.0404(5) Uani d 1
H H6 0.0710 0.4867 0.3383 0.049 Uiso calc 1
C C7 0.10898(11) 0.5321(3) 0.43086(10) 0.0425(5) Uani d 1
H H7 0.0684 0.5942 0.4460 0.051 Uiso calc 1
C C8 0.22034(10) 0.2696(3) 0.23446(9) 0.0363(5) Uani d 1
C C9 0.19429(11) 0.1899(3) 0.16929(9) 0.0406(5) Uani d 1
H H9A 0.1574 0.1017 0.1791 0.049 Uiso calc 1
H H9B 0.2352 0.1303 0.1482 0.049 Uiso calc 1
C C10 0.06326(9) 0.3615(3) 0.13367(9) 0.0299(4) Uani d 1
C C11 -0.04605(9) 0.4777(3) 0.10243(9) 0.0325(4) Uani d 1
C C12 -0.07491(10) 0.4288(3) 0.16389(9) 0.0349(5) Uani d 1
H H12 -0.1223 0.4598 0.1760 0.042 Uiso calc 1
C C13 -0.03109(10) 0.3332(3) 0.20616(9) 0.0325(5) Uani d 1
N N1 -0.08541(11) 0.5584(3) 0.05502(9) 0.0468(5) Uani d 1
N N2 -0.05566(11) 0.2679(3) 0.26481(8) 0.0457(5) Uani d 1
N N3 0.04068(8) 0.3016(2) 0.19228(7) 0.0335(4) Uani d 1
N N4 0.02461(8) 0.4414(2) 0.08647(7) 0.0339(4) Uani d 1
N N5 0.16624(9) 0.3033(2) 0.27763(8) 0.0366(4) Uani d 1
O O1 0.28525(7) 0.2957(2) 0.24536(7) 0.0565(5) Uani d 1
O O2 0.17327(8) 0.5664(2) 0.53655(7) 0.0524(4) Uani d 1
S S1 0.15638(2) 0.34642(8) 0.11078(2) 0.03976(17) Uani d 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 0.0016 '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'
S S 0.1246 0.1234 '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
O2 C1 H1A 109.5
O2 C1 H1B 109.5
H1A C1 H1B 109.5
O2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O2 C2 C7 124.45(19)
O2 C2 C3 116.15(17)
C7 C2 C3 119.40(18)
C4 C3 C2 121.13(18)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 119.78(18)
C3 C4 H4 120.1
C5 C4 H4 120.1
C6 C5 C4 118.82(18)
C6 C5 N5 118.06(16)
C4 C5 N5 122.95(18)
C5 C6 C7 121.46(18)
C5 C6 H6 119.3
C7 C6 H6 119.3
C2 C7 C6 119.38(19)
C2 C7 H7 120.3
C6 C7 H7 120.3
O1 C8 N5 124.76(19)
O1 C8 C9 121.55(17)
N5 C8 C9 113.67(16)
C8 C9 S1 114.65(15)
C8 C9 H9A 108.6
S1 C9 H9A 108.6
C8 C9 H9B 108.6
S1 C9 H9B 108.6
H9A C9 H9B 107.6
N3 C10 N4 128.54(16)
N3 C10 S1 120.52(13)
N4 C10 S1 110.91(13)
N1 C11 N4 115.81(17)
N1 C11 C12 123.17(17)
N4 C11 C12 121.00(16)
C13 C12 C11 117.83(17)
C13 C12 H12 121.1
C11 C12 H12 121.1
N2 C13 N3 115.64(17)
N2 C13 C12 122.45(17)
N3 C13 C12 121.89(16)
C11 N1 H1D 119.2(15)
C11 N1 H1E 119.7(16)
H1D N1 H1E 121(2)
C13 N2 H2A 119.3(14)
C13 N2 H2B 116.0(14)
H2A N2 H2B 120(2)
C10 N3 C13 114.85(15)
C10 N4 C11 115.47(15)
C8 N5 C5 129.15(17)
C8 N5 H5 114.1(13)
C5 N5 H5 116.1(14)
C2 O2 C1 117.90(17)
C10 S1 C9 104.07(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.402(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 O2 1.373(2)
C2 C7 1.382(3)
C2 C3 1.384(3)
C3 C4 1.378(3)
C3 H3 0.9300
C4 C5 1.391(2)
C4 H4 0.9300
C5 C6 1.381(3)
C5 N5 1.413(2)
C6 C7 1.385(3)
C6 H6 0.9300
C7 H7 0.9300
C8 O1 1.222(2)
C8 N5 1.339(2)
C8 C9 1.517(3)
C9 S1 1.808(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 N3 1.326(2)
C10 N4 1.328(2)
C10 S1 1.7664(17)
C11 N1 1.341(2)
C11 N4 1.359(2)
C11 C12 1.391(2)
C12 C13 1.373(3)
C12 H12 0.9300
C13 N2 1.353(2)
C13 N3 1.362(2)
N1 H1D 0.91(2)
N1 H1E 0.81(2)
N2 H2A 0.91(2)
N2 H2B 0.87(2)
N5 H5 0.84(2)
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
N1 H1D N4 5_565 0.91(2) 2.17(2) 3.048(2) 164.2(2)
N2 H2B O1 6_556 0.87(2) 2.08(2) 2.922(2) 163.1(2)
N5 H5 N3 . 0.84(2) 2.06(2) 2.863(2) 160.3(2)
N2 H2A Cg1 3_545 0.91(2) 2.620(10) 3.533(2) 156.7(2)
C4 H4 Cg2 8_655 0.93 2.76 3.623(2) 134
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
O2 C2 C3 C4 -178.18(19)
C7 C2 C3 C4 1.4(3)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 -1.3(3)
C3 C4 C5 N5 -176.38(19)
C4 C5 C6 C7 1.1(3)
N5 C5 C6 C7 176.5(2)
O2 C2 C7 C6 178.01(19)
C3 C2 C7 C6 -1.5(3)
C5 C6 C7 C2 0.3(3)
O1 C8 C9 S1 -102.2(2)
N5 C8 C9 S1 79.2(2)
N1 C11 C12 C13 174.4(2)
N4 C11 C12 C13 -4.0(3)
C11 C12 C13 N2 -174.90(19)
C11 C12 C13 N3 6.7(3)
N4 C10 N3 C13 -2.8(3)
S1 C10 N3 C13 175.11(14)
N2 C13 N3 C10 177.94(18)
C12 C13 N3 C10 -3.5(3)
N3 C10 N4 C11 5.3(3)
S1 C10 N4 C11 -172.79(14)
N1 C11 N4 C10 179.97(18)
C12 C11 N4 C10 -1.5(3)
O1 C8 N5 C5 0.2(4)
C9 C8 N5 C5 178.83(19)
C6 C5 N5 C8 152.0(2)
C4 C5 N5 C8 -32.9(3)
C7 C2 O2 C1 5.7(3)
C3 C2 O2 C1 -174.8(2)
N3 C10 S1 C9 15.55(19)
N4 C10 S1 C9 -166.19(14)
C8 C9 S1 C10 -86.82(15)

_cod_database_fobs_code 1549348
