#------------------------------------------------------------------------------
#$Date: 2018-04-30 19:25:27 +0300 (Mon, 30 Apr 2018) $
#$Revision: 207548 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/24/2242452.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_2242452
loop_
_publ_author_name
'Choudhury, Manisha'
'Viswanathan, Vijayan'
'Timiri, Ajay Kumar'
'Sinha, Barij Nayan'
'Jeyaprakash, Venkatesan'
'Velmurugan, Devadasan'
_publ_section_title
;
 Crystal structures and Hirshfeld surface analyses of
 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(pyridin-2-yl)acetamide
 and
 2-[(4,6-diaminopyrimidin-2-yl)sulfanyl]-N-(pyrazin-2-yl)acetamide
;
_journal_coeditor_code           SU5430
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              718
_journal_page_last               723
_journal_paper_doi               10.1107/S2056989018005704
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C11 H12 N6 O S'
_chemical_formula_moiety         'C11 H12 N6 O S'
_chemical_formula_sum            'C11 H12 N6 O S'
_chemical_formula_weight         276.33
_chemical_name_systematic
;
2-[(4,6-Diaminopyrimidin-2-yl)sulfanyl]-N-(pyridin-2-yl)acetamide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                95.8200(10)
_cell_angle_beta                 91.1160(10)
_cell_angle_gamma                105.6820(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2341(2)
_cell_length_b                   9.3852(2)
_cell_length_c                   9.7971(2)
_cell_measurement_reflns_used    2605
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.428
_cell_measurement_theta_min      2.092
_cell_volume                     636.33(3)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_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 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9447
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.428
_diffrn_reflns_theta_min         2.092
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0340
_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)+(0.0443P)²+0.1669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                2160
_reflns_number_total             2605
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5430sup1.cif
_cod_data_source_block           I
_cod_database_code               2242452
_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   0.927
_shelx_estimated_absorpt_t_max   0.950
loop_
_space_group_symop_operation_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_occupancy
S S1 0.47564(6) 0.24187(5) 0.97878(4) 0.04443(15) Uani d 1
O O1 0.1201(2) -0.07191(14) 0.81504(14) 0.0637(4) Uani d 1
N N1 0.4212(3) 0.58093(19) 0.63223(17) 0.0509(4) Uani d 1
H H1A 0.470(3) 0.652(2) 0.584(2) 0.059(6) Uiso d 1
H H1B 0.299(3) 0.546(2) 0.641(2) 0.066(7) Uiso d 1
N N2 1.0373(2) 0.60541(19) 0.83751(19) 0.0500(4) Uani d 1
H H2A 1.087(3) 0.696(2) 0.820(2) 0.059(6) Uiso d 1
H H2B 1.092(3) 0.590(2) 0.914(2) 0.071(7) Uiso d 1
N N3 0.45530(19) 0.42030(14) 0.78589(14) 0.0378(3) Uani d 1
N N4 0.75997(18) 0.44133(14) 0.89781(13) 0.0374(3) Uani d 1
N N5 0.2555(2) 0.10689(16) 0.67916(14) 0.0395(3) Uani d 1
H H5 0.304(3) 0.201(2) 0.6830(18) 0.046(5) Uiso d 1
N N6 0.3287(2) 0.11118(16) 0.45436(15) 0.0458(4) Uani d 1
C C1 0.5404(2) 0.53494(17) 0.71413(16) 0.0373(4) Uani d 1
C C2 0.7366(2) 0.59919(18) 0.72509(17) 0.0398(4) Uani d 1
H H2 0.795008 0.672763 0.670694 0.048 Uiso calc 1
C C3 0.8435(2) 0.55043(16) 0.81970(16) 0.0367(4) Uani d 1
C C4 0.5717(2) 0.38421(16) 0.87394(15) 0.0351(4) Uani d 1
C C5 0.2265(2) 0.17793(19) 0.91965(17) 0.0452(4) Uani d 1
H H5A 0.149123 0.139634 0.994486 0.054 Uiso calc 1
H H5B 0.185101 0.261192 0.891905 0.054 Uiso calc 1
C C6 0.1943(2) 0.05740(18) 0.80001(18) 0.0415(4) Uani d 1
C C7 0.2500(2) 0.02603(17) 0.55029(17) 0.0369(4) Uani d 1
C C8 0.1697(3) -0.12615(19) 0.5237(2) 0.0506(4) Uani d 1
H H8 0.118824 -0.182978 0.593511 0.061 Uiso calc 1
C C9 0.1674(3) -0.1909(2) 0.3911(2) 0.0603(5) Uani d 1
H H9 0.113148 -0.292746 0.369861 0.072 Uiso calc 1
C C10 0.2447(3) -0.1056(2) 0.2905(2) 0.0574(5) Uani d 1
H H10 0.243138 -0.147400 0.200125 0.069 Uiso calc 1
C C11 0.3246(3) 0.0435(2) 0.32694(19) 0.0551(5) Uani d 1
H H11 0.379420 0.101358 0.258857 0.066 Uiso calc 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
C4 S1 C5 102.83(8)
C1 N1 H1A 118.3(14)
C1 N1 H1B 117.3(15)
H1A N1 H1B 124(2)
C3 N2 H2A 117.2(13)
C3 N2 H2B 117.6(15)
H2A N2 H2B 110(2)
C4 N3 C1 114.94(13)
C4 N4 C3 115.04(13)
C6 N5 C7 129.23(14)
C6 N5 H5 114.6(12)
C7 N5 H5 116.2(12)
C7 N6 C11 116.91(15)
N1 C1 N3 115.65(15)
N1 C1 C2 122.72(15)
N3 C1 C2 121.63(15)
C1 C2 C3 117.79(14)
C1 C2 H2 121.1
C3 C2 H2 121.1
N4 C3 N2 116.08(15)
N4 C3 C2 121.51(14)
N2 C3 C2 122.39(15)
N3 C4 N4 128.88(14)
N3 C4 S1 119.16(12)
N4 C4 S1 111.95(12)
C6 C5 S1 111.72(12)
C6 C5 H5A 109.3
S1 C5 H5A 109.3
C6 C5 H5B 109.3
S1 C5 H5B 109.3
H5A C5 H5B 107.9
O1 C6 N5 124.47(16)
O1 C6 C5 121.07(15)
N5 C6 C5 114.46(14)
N6 C7 C8 123.05(16)
N6 C7 N5 112.92(13)
C8 C7 N5 124.02(15)
C9 C8 C7 118.03(18)
C9 C8 H8 121.0
C7 C8 H8 121.0
C10 C9 C8 120.00(18)
C10 C9 H9 120.0
C8 C9 H9 120.0
C9 C10 C11 117.86(18)
C9 C10 H10 121.1
C11 C10 H10 121.1
N6 C11 C10 124.13(18)
N6 C11 H11 117.9
C10 C11 H11 117.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.7682(15)
S1 C5 1.8021(18)
O1 C6 1.2124(19)
N1 C1 1.348(2)
N1 H1A 0.86(2)
N1 H1B 0.86(2)
N2 C3 1.358(2)
N2 H2A 0.86(2)
N2 H2B 0.88(2)
N3 C4 1.324(2)
N3 C1 1.358(2)
N4 C4 1.328(2)
N4 C3 1.3570(19)
N5 C6 1.354(2)
N5 C7 1.400(2)
N5 H5 0.856(19)
N6 C7 1.332(2)
N6 C11 1.338(2)
C1 C2 1.381(2)
C2 C3 1.384(2)
C2 H2 0.9300
C5 C6 1.512(2)
C5 H5A 0.9700
C5 H5B 0.9700
C7 C8 1.384(2)
C8 C9 1.376(3)
C8 H8 0.9300
C9 C10 1.365(3)
C9 H9 0.9300
C10 C11 1.368(3)
C10 H10 0.9300
C11 H11 0.9300
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
N5 H5 N3 . 0.86(2) 2.18(2) 2.975(2) 154(2)
C8 H8 O1 . 0.93 2.31 2.894(2) 121
N2 H2B N4 2_767 0.88(2) 2.20(2) 3.082(2) 178(2)
N1 H1A N6 2_666 0.86(2) 2.38(2) 3.174(2) 155(2)
N2 H2A O1 1_665 0.86(2) 2.13(2) 2.956(2) 159(2)
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
C4 N3 C1 N1 -174.86(14)
C4 N3 C1 C2 5.2(2)
N1 C1 C2 C3 175.39(15)
N3 C1 C2 C3 -4.7(2)
C4 N4 C3 N2 -176.87(14)
C4 N4 C3 C2 1.5(2)
C1 C2 C3 N4 1.2(2)
C1 C2 C3 N2 179.38(15)
C1 N3 C4 N4 -2.5(2)
C1 N3 C4 S1 177.30(10)
C3 N4 C4 N3 -0.8(2)
C3 N4 C4 S1 179.39(10)
C5 S1 C4 N3 3.32(14)
C5 S1 C4 N4 -176.85(11)
C4 S1 C5 C6 87.65(13)
C7 N5 C6 O1 -0.5(3)
C7 N5 C6 C5 179.12(15)
S1 C5 C6 O1 105.06(17)
S1 C5 C6 N5 -74.58(17)
C11 N6 C7 C8 1.2(2)
C11 N6 C7 N5 -178.11(15)
C6 N5 C7 N6 -178.11(16)
C6 N5 C7 C8 2.5(3)
N6 C7 C8 C9 -1.7(3)
N5 C7 C8 C9 177.57(17)
C7 C8 C9 C10 0.7(3)
C8 C9 C10 C11 0.7(3)
C7 N6 C11 C10 0.2(3)
C9 C10 C11 N6 -1.2(3)

_cod_database_fobs_code 2242452
