#------------------------------------------------------------------------------
#$Date: 2018-04-30 18:25:27 +0200 (lun 30 de abr de 2018) $
#$Revision: 207548 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/24/2242453.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_2242453
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          'C10 H11 N7 O S'
_chemical_formula_moiety         'C10 H11 N7 O S'
_chemical_formula_sum            'C10 H11 N7 O S'
_chemical_formula_weight         277.32
_chemical_name_systematic
;
2-[(4,6-Diaminopyrimidin-2-yl)sulfanyl]-N-(pyrazin-2-yl)acetamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                90
_cell_angle_beta                 94.307(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1333(5)
_cell_length_b                   8.1561(3)
_cell_length_c                   12.8442(5)
_cell_measurement_reflns_used    3124
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.284
_cell_measurement_theta_min      2.227
_cell_volume                     1267.48(9)
_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 0.992
_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  0.0842
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.284
_diffrn_reflns_theta_min         2.227
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.233
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.1718
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0452P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1262
_reflns_number_gt                1320
_reflns_number_total             3124
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5430sup1.cif
_cod_data_source_block           II
_cod_database_code               2242453
_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   0.931
_shelx_estimated_absorpt_t_max   0.950
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_occupancy
S S1 0.77107(6) 0.20394(11) 0.50448(6) 0.0525(3) Uani d 1
O O1 1.06221(18) 0.2503(3) 0.55054(17) 0.0779(8) Uani d 1
N N1 0.6951(3) 0.2961(4) 0.8740(2) 0.0651(9) Uani d 1
H H1A 0.651(3) 0.297(4) 0.923(3) 0.084(13) Uiso d 1
H H1B 0.760(3) 0.342(4) 0.881(3) 0.079(13) Uiso d 1
N N2 0.4369(2) 0.0046(4) 0.6423(3) 0.0635(9) Uani d 1
H H2A 0.391(2) -0.015(4) 0.687(2) 0.060(11) Uiso d 1
H H2B 0.423(2) -0.044(4) 0.571(3) 0.080(11) Uiso d 1
N N3 0.72886(19) 0.2473(3) 0.70403(17) 0.0452(7) Uani d 1
N N4 0.59901(19) 0.1011(3) 0.58901(17) 0.0463(7) Uani d 1
N N5 0.9712(2) 0.1889(3) 0.69294(19) 0.0494(7) Uani d 1
H H5 0.912(2) 0.197(4) 0.719(2) 0.057(11) Uiso d 1
N N6 1.0164(2) 0.0445(3) 0.84291(19) 0.0545(7) Uani d 1
N N7 1.2266(2) -0.0273(4) 0.7815(2) 0.0659(8) Uani d 1
C C1 0.6580(3) 0.2321(4) 0.7813(2) 0.0450(8) Uani d 1
C C2 0.5579(2) 0.1540(4) 0.7649(2) 0.0466(8) Uani d 1
H H2 0.509877 0.146453 0.817830 0.056 Uiso calc 1
C C3 0.5306(2) 0.0872(4) 0.6680(2) 0.0438(8) Uani d 1
C C4 0.6909(2) 0.1845(4) 0.6132(2) 0.0421(7) Uani d 1
C C5 0.8779(2) 0.3427(4) 0.5525(2) 0.0497(9) Uani d 1
H H5A 0.897729 0.412594 0.495784 0.060 Uiso calc 1
H H5B 0.849528 0.412281 0.605640 0.060 Uiso calc 1
C C6 0.9796(3) 0.2561(4) 0.5981(2) 0.0499(9) Uani d 1
C C7 1.0498(2) 0.0968(4) 0.7528(2) 0.0440(8) Uani d 1
C C8 1.1544(3) 0.0605(4) 0.7222(3) 0.0613(10) Uani d 1
H H8 1.174535 0.098921 0.658172 0.074 Uiso calc 1
C C9 1.1922(3) -0.0808(4) 0.8710(3) 0.0610(10) Uani d 1
H H9 1.239366 -0.144894 0.914481 0.073 Uiso calc 1
C C10 1.0895(3) -0.0446(4) 0.9011(2) 0.0598(9) Uani d 1
H H10 1.069630 -0.083866 0.965011 0.072 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 102.17(14)
C1 N1 H1A 118(2)
C1 N1 H1B 120(2)
H1A N1 H1B 122(3)
C3 N2 H2A 121(2)
C3 N2 H2B 120.4(17)
H2A N2 H2B 118(3)
C4 N3 C1 114.1(2)
C4 N4 C3 114.7(3)
C6 N5 C7 128.4(3)
C6 N5 H5 118(2)
C7 N5 H5 114(2)
C7 N6 C10 115.5(3)
C8 N7 C9 116.0(3)
N1 C1 N3 114.9(3)
N1 C1 C2 123.3(3)
N3 C1 C2 121.9(3)
C1 C2 C3 118.2(3)
C1 C2 H2 120.9
C3 C2 H2 120.9
N2 C3 N4 114.2(3)
N2 C3 C2 124.3(3)
N4 C3 C2 121.4(3)
N4 C4 N3 129.6(3)
N4 C4 S1 111.4(2)
N3 C4 S1 119.0(2)
C6 C5 S1 112.8(2)
C6 C5 H5A 109.0
S1 C5 H5A 109.0
C6 C5 H5B 109.0
S1 C5 H5B 109.0
H5A C5 H5B 107.8
O1 C6 N5 124.1(3)
O1 C6 C5 120.5(3)
N5 C6 C5 115.4(3)
N6 C7 C8 121.7(3)
N6 C7 N5 114.4(3)
C8 C7 N5 124.0(3)
N7 C8 C7 122.1(3)
N7 C8 H8 119.0
C7 C8 H8 119.0
N7 C9 C10 121.9(3)
N7 C9 H9 119.1
C10 C9 H9 119.1
N6 C10 C9 122.9(3)
N6 C10 H10 118.5
C9 C10 H10 118.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.768(3)
S1 C5 1.795(3)
O1 C6 1.213(3)
N1 C1 1.346(4)
N1 H1A 0.86(3)
N1 H1B 0.88(3)
N2 C3 1.341(4)
N2 H2A 0.85(3)
N2 H2B 1.00(3)
N3 C4 1.325(3)
N3 C1 1.367(3)
N4 C4 1.323(3)
N4 C3 1.364(3)
N5 C6 1.347(4)
N5 C7 1.398(4)
N5 H5 0.82(3)
N6 C7 1.325(3)
N6 C10 1.331(4)
N7 C8 1.326(4)
N7 C9 1.326(4)
C1 C2 1.374(4)
C2 C3 1.375(4)
C2 H2 0.9300
C5 C6 1.502(4)
C5 H5A 0.9700
C5 H5B 0.9700
C7 C8 1.389(4)
C8 H8 0.9300
C9 C10 1.364(4)
C9 H9 0.9300
C10 H10 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 . 0.82(3) 2.25(3) 2.993(4) 151(3)
C8 H8 O1 . 0.93 2.24 2.854(4) 123
N2 H2B N4 3_656 1.00(3) 2.11(3) 3.092(4) 169(3)
N1 H1A O1 4_566 0.86(3) 2.06(4) 2.904(4) 167(3)
N2 H2A N7 1_455 0.85(3) 2.41(3) 3.235(4) 164(3)
C9 H9 O1 2_746 0.93 2.56 3.368(4) 145
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 -179.7(3)
C4 N3 C1 C2 1.7(4)
N1 C1 C2 C3 -177.3(3)
N3 C1 C2 C3 1.3(5)
C4 N4 C3 N2 179.0(3)
C4 N4 C3 C2 -0.9(4)
C1 C2 C3 N2 178.4(3)
C1 C2 C3 N4 -1.7(5)
C3 N4 C4 N3 4.6(5)
C3 N4 C4 S1 -177.3(2)
C1 N3 C4 N4 -5.0(5)
C1 N3 C4 S1 177.1(2)
C5 S1 C4 N4 172.4(2)
C5 S1 C4 N3 -9.3(3)
C4 S1 C5 C6 93.4(2)
C7 N5 C6 O1 -2.8(5)
C7 N5 C6 C5 177.6(3)
S1 C5 C6 O1 105.2(3)
S1 C5 C6 N5 -75.2(3)
C10 N6 C7 C8 -0.1(5)
C10 N6 C7 N5 179.5(3)
C6 N5 C7 N6 -178.8(3)
C6 N5 C7 C8 0.8(5)
C9 N7 C8 C7 1.1(5)
N6 C7 C8 N7 -0.4(5)
N5 C7 C8 N7 180.0(3)
C8 N7 C9 C10 -1.3(5)
C7 N6 C10 C9 -0.1(5)
N7 C9 C10 N6 0.9(5)

_cod_database_fobs_code 2242453
