#------------------------------------------------------------------------------
#$Date: 2020-09-16 08:04:07 +0300 (Wed, 16 Sep 2020) $
#$Revision: 256454 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/90/1559092.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_1559092
loop_
_publ_author_name
'Chakkarapani, Nandhini'
'Murugan, Suganya'
'Ibrahim, Abdul Razak'
'Kavitha, Savaridasan Jose'
'Hemamalini, Madhukar'
'Rajakannan, Venkatachalam'
_publ_section_title
;
 2,6-Diamino-4-chloropyrimidine--succinic acid (2/1)
;
_journal_coeditor_code           HB4365
_journal_issue                   9
_journal_name_full               IUCrData
_journal_page_first              x201239
_journal_paper_doi               10.1107/S2414314620012390
_journal_volume                  5
_journal_year                    2020
_chemical_formula_iupac          '2C4 H5 Cl N4, C4 H6 O4'
_chemical_formula_moiety         '2(C4 H5 Cl N4), C4 H6 O4'
_chemical_formula_sum            'C12 H16 Cl2 N8 O4'
_chemical_formula_weight         407.23
_chemical_name_systematic
;
2,6-Diamino-4-chloropyrimidine--succinic acid (2/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 98.603(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.2096(14)
_cell_length_b                   4.9765(5)
_cell_length_c                   13.5673(14)
_cell_measurement_reflns_used    3778
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.85
_cell_measurement_theta_min      2.62
_cell_volume                     881.85(16)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD '
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15031
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.185
_diffrn_reflns_theta_min         1.559
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.720
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.437
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0434
_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)+(0.0642P)²+0.3195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1282
_reflns_number_gt                2102
_reflns_number_total             2599
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4365sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1559092
_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   0.759
_shelx_estimated_absorpt_t_max   0.949
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.58724(4) 0.10526(9) 0.74117(4) 0.06071(19) Uani d 1 . .
N N2 0.74496(9) 0.7549(3) 0.60431(9) 0.0345(3) Uani d 1 . .
O O2 0.81782(9) 1.1416(3) 0.50401(9) 0.0504(3) Uani d 1 . .
H H2 0.803150 1.017333 0.538975 0.076 Uiso calc 1 . .
O O1 0.96386(9) 1.1222(3) 0.60813(9) 0.0523(3) Uani d 1 . .
N N1 0.60385(10) 0.4544(3) 0.60332(10) 0.0400(3) Uani d 1 . .
C C5 0.90949(11) 1.2237(3) 0.53630(11) 0.0367(3) Uani d 1 . .
C C2 0.74276(13) 0.4470(3) 0.73964(12) 0.0420(4) Uani d 1 . .
H H2A 0.771513 0.374017 0.800544 0.050 Uiso calc 1 . .
C C4 0.65260(11) 0.6548(3) 0.56340(11) 0.0358(3) Uani d 1 . .
C C6 0.94673(11) 1.4522(3) 0.47896(12) 0.0391(3) Uani d 1 . .
H H6A 0.899454 1.601474 0.478469 0.047 Uiso calc 1 . .
H H6B 0.946393 1.395885 0.410457 0.047 Uiso calc 1 . .
N N4 0.88038(11) 0.7585(3) 0.73071(11) 0.0514(4) Uani d 1 . .
H H4A 0.906878 0.884453 0.699449 0.062 Uiso calc 1 . .
H H4B 0.912066 0.700416 0.786646 0.062 Uiso calc 1 . .
C C1 0.65147(12) 0.3614(3) 0.68959(12) 0.0392(3) Uani d 1 . .
C C3 0.79074(11) 0.6540(3) 0.69271(11) 0.0364(3) Uani d 1 . .
N N3 0.60778(11) 0.7630(3) 0.47853(11) 0.0532(4) Uani d 1 . .
H H3A 0.549166 0.704581 0.450636 0.064 Uiso calc 1 . .
H H3B 0.637362 0.891492 0.451444 0.064 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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N2 C4 . . 118.71(13) ?
C5 O2 H2 . . 109.5 ?
C1 N1 C4 . . 114.95(13) ?
O1 C5 O2 . . 123.08(14) ?
O1 C5 C6 . . 121.62(13) ?
O2 C5 C6 . . 115.30(13) ?
C1 C2 C3 . . 115.32(14) ?
C1 C2 H2A . . 122.3 ?
C3 C2 H2A . . 122.3 ?
N3 C4 N1 . . 118.16(13) ?
N3 C4 N2 . . 117.58(14) ?
N1 C4 N2 . . 124.26(14) ?
C5 C6 C6 . 3_786 113.62(16) ?
C5 C6 H6A . . 108.8 ?
C6 C6 H6A 3_786 . 108.8 ?
C5 C6 H6B . . 108.8 ?
C6 C6 H6B 3_786 . 108.8 ?
H6A C6 H6B . . 107.7 ?
C3 N4 H4A . . 120.0 ?
C3 N4 H4B . . 120.0 ?
H4A N4 H4B . . 120.0 ?
N1 C1 C2 . . 126.81(14) ?
N1 C1 Cl1 . . 114.59(12) ?
C2 C1 Cl1 . . 118.61(13) ?
N4 C3 N2 . . 116.94(14) ?
N4 C3 C2 . . 123.14(14) ?
N2 C3 C2 . . 119.91(14) ?
C4 N3 H3A . . 120.0 ?
C4 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.7356(16) ?
N2 C3 . 1.3561(18) ?
N2 C4 . 1.3572(18) ?
O2 C5 . 1.2911(17) ?
O2 H2 . 0.8200 ?
O1 C5 . 1.2294(19) ?
N1 C1 . 1.327(2) ?
N1 C4 . 1.3443(19) ?
C5 C6 . 1.501(2) ?
C2 C1 . 1.361(2) ?
C2 C3 . 1.410(2) ?
C2 H2A . 0.9300 ?
C4 N3 . 1.327(2) ?
C6 C6 3_786 1.514(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
N4 C3 . 1.325(2) ?
N4 H4A . 0.8600 ?
N4 H4B . 0.8600 ?
N3 H3A . 0.8600 ?
N3 H3B . 0.8600 ?
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
O2 H2 N2 . 0.82 1.81 2.622(2) 169 yes
N3 H3A N1 3_666 0.86 2.19 3.048(2) 173 yes
N4 H4A O1 . 0.86 1.94 2.794(2) 169 yes
N4 H4B O1 2_746 0.86 2.04 2.8510(19) 156 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 C4 N3 . . . . -178.01(15) ?
C1 N1 C4 N2 . . . . 1.9(2) ?
C3 N2 C4 N3 . . . . 177.81(15) ?
C3 N2 C4 N1 . . . . -2.1(2) ?
O1 C5 C6 C6 . . . 3_786 -2.5(3) ?
O2 C5 C6 C6 . . . 3_786 178.28(18) ?
C4 N1 C1 C2 . . . . -0.4(2) ?
C4 N1 C1 Cl1 . . . . 179.33(11) ?
C3 C2 C1 N1 . . . . -0.8(3) ?
C3 C2 C1 Cl1 . . . . 179.50(12) ?
C4 N2 C3 N4 . . . . -179.40(14) ?
C4 N2 C3 C2 . . . . 0.7(2) ?
C1 C2 C3 N4 . . . . -179.27(16) ?
C1 C2 C3 N2 . . . . 0.6(2) ?

_cod_database_fobs_code 1559092
