#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/69/2236934.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_2236934
loop_
_publ_author_name
'Thanigaimani, Kaliyaperumal'
'Khalib, Nuridayanti Che'
'Arshad, Suhana'
'Razak, Ibrahim Abdul'
_publ_section_title
;
 2,6-Diamino-4-chloropyrimidine--benzoic acid (1/1)
;
_journal_coeditor_code           IS5218
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3442
_journal_page_last               o3443
_journal_paper_doi               10.1107/S160053681204768X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C4 H5 Cl N4, C7 H6 O2'
_chemical_formula_moiety         'C4 H5 Cl N4, C7 H6 O2'
_chemical_formula_sum            'C11 H11 Cl N4 O2'
_chemical_formula_weight         266.69
_chemical_name_systematic
;
2,6-Diamino-4-chloropyrimidine--benzoic acid (1/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.493(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7817(17)
_cell_length_b                   5.7032(12)
_cell_length_c                   24.026(4)
_cell_measurement_reflns_used    5646
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      3.02
_cell_volume                     1197.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7539
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.9505
_exptl_absorpt_correction_T_min  0.8952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2097
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.4196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                1891
_reflns_number_total             2097
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5218.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236934
_cod_database_fobs_code          2236934
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 -0.05557(4) 0.64565(9) 0.367228(16) 0.03348(18) Uani d . 1 1
O O1 0.43197(13) 0.5175(2) 0.61239(5) 0.0312(3) Uani d D 1 1
O O2 0.52962(16) 0.1720(2) 0.59015(5) 0.0372(3) Uani d . 1 1
N N1 0.07033(15) 0.7543(3) 0.46563(5) 0.0274(4) Uani d . 1 1
N N2 0.27154(14) 0.5362(3) 0.51588(5) 0.0266(4) Uani d . 1 1
N N3 0.16941(19) 0.8669(3) 0.55310(6) 0.0313(4) Uani d . 1 1
N N4 0.37676(16) 0.2112(3) 0.47835(7) 0.0325(4) Uani d . 1 1
C C1 0.07703(17) 0.5991(3) 0.42471(7) 0.0272(4) Uani d . 1 1
C C2 0.17389(17) 0.4136(4) 0.42399(7) 0.0287(4) Uani d . 1 1
H H2A 0.1734 0.3108 0.3929 0.034 Uiso calc R 1 1
C C3 0.27541(17) 0.3846(3) 0.47284(7) 0.0272(4) Uani d . 1 1
C C4 0.17144(17) 0.7163(3) 0.51057(6) 0.0265(4) Uani d . 1 1
C C5 0.71603(19) 0.1587(3) 0.69200(7) 0.0264(4) Uani d . 1 1
H H5A 0.7220 0.0302 0.6672 0.032 Uiso calc R 1 1
C C6 0.80722(19) 0.1626(3) 0.74236(7) 0.0276(4) Uani d . 1 1
H H6A 0.8760 0.0372 0.7519 0.033 Uiso calc R 1 1
C C7 0.79790(17) 0.3497(3) 0.77877(7) 0.0251(4) Uani d . 1 1
H H7A 0.8608 0.3526 0.8132 0.030 Uiso calc R 1 1
C C8 0.69723(17) 0.5321(3) 0.76507(7) 0.0258(4) Uani d . 1 1
H H8A 0.6908 0.6594 0.7902 0.031 Uiso calc R 1 1
C C9 0.60544(17) 0.5293(3) 0.71455(7) 0.0241(4) Uani d . 1 1
H H9A 0.5361 0.6542 0.7052 0.029 Uiso calc R 1 1
C C10 0.61545(17) 0.3430(3) 0.67768(6) 0.0214(4) Uani d . 1 1
C C11 0.52134(18) 0.3366(3) 0.62273(7) 0.0249(4) Uani d . 1 1
H H2N3 0.233(3) 0.851(4) 0.5785(10) 0.039(6) Uiso d . 1 1
H H2N4 0.432(2) 0.196(4) 0.5105(10) 0.045(6) Uiso d . 1 1
H H1N4 0.388(2) 0.113(4) 0.4508(9) 0.033(5) Uiso d . 1 1
H H1N3 0.109(2) 0.983(4) 0.5499(9) 0.037(6) Uiso d . 1 1
H H1O1 0.386(3) 0.508(7) 0.5789(7) 0.113(13) Uiso d D 1 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
C11 O1 H1O1 110(2)
C1 N1 C4 114.40(16)
C4 N2 C3 118.60(14)
C4 N3 H2N3 117.1(16)
C4 N3 H1N3 119.2(15)
H2N3 N3 H1N3 123(2)
C3 N4 H2N4 118.1(15)
C3 N4 H1N4 121.4(13)
H2N4 N4 H1N4 121(2)
N1 C1 C2 126.90(15)
N1 C1 Cl1 114.35(13)
C2 C1 Cl1 118.76(14)
C1 C2 C3 115.25(17)
C1 C2 H2A 122.4
C3 C2 H2A 122.4
N4 C3 N2 117.76(15)
N4 C3 C2 122.23(17)
N2 C3 C2 120.01(17)
N3 C4 N1 116.94(17)
N3 C4 N2 118.24(15)
N1 C4 N2 124.81(16)
C6 C5 C10 120.18(16)
C6 C5 H5A 119.9
C10 C5 H5A 119.9
C5 C6 C7 119.92(16)
C5 C6 H6A 120.0
C7 C6 H6A 120.0
C8 C7 C6 120.20(15)
C8 C7 H7A 119.9
C6 C7 H7A 119.9
C7 C8 C9 120.15(16)
C7 C8 H8A 119.9
C9 C8 H8A 119.9
C10 C9 C8 119.83(15)
C10 C9 H9A 120.1
C8 C9 H9A 120.1
C9 C10 C5 119.71(15)
C9 C10 C11 121.29(15)
C5 C10 C11 118.99(15)
O2 C11 O1 123.62(15)
O2 C11 C10 121.44(16)
O1 C11 C10 114.94(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7395(15)
O1 C11 1.306(2)
O1 H1O1 0.866(10)
O2 C11 1.229(2)
N1 C1 1.328(2)
N1 C4 1.348(2)
N2 C4 1.350(2)
N2 C3 1.351(2)
N3 C4 1.336(2)
N3 H2N3 0.79(2)
N3 H1N3 0.85(2)
N4 C3 1.328(3)
N4 H2N4 0.88(2)
N4 H1N4 0.88(2)
C1 C2 1.358(3)
C2 C3 1.414(2)
C2 H2A 0.9500
C5 C6 1.386(2)
C5 C10 1.395(2)
C5 H5A 0.9500
C6 C7 1.387(3)
C6 H6A 0.9500
C7 C8 1.384(2)
C7 H7A 0.9500
C8 C9 1.392(2)
C8 H8A 0.9500
C9 C10 1.391(2)
C9 H9A 0.9500
C10 C11 1.490(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
_geom_hbond_publ_flag
O1 H1O1 N2 . 0.867(18) 1.74(2) 2.5976(18) 168(3) yes
N4 H2N4 O2 . 0.88(2) 2.03(2) 2.894(2) 171.2(18) yes
N4 H1N4 O2 3_656 0.88(2) 2.07(2) 2.902(2) 158.2(19) yes
N3 H1N3 N1 3_576 0.85(2) 2.18(2) 3.020(2) 171(2) yes
C9 H9A Cg1 2_656 0.95 2.99 3.6557(19) 128 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
C4 N1 C1 C2 -0.5(2)
C4 N1 C1 Cl1 179.02(11)
N1 C1 C2 C3 1.1(3)
Cl1 C1 C2 C3 -178.45(11)
C4 N2 C3 N4 178.65(15)
C4 N2 C3 C2 -1.2(2)
C1 C2 C3 N4 179.98(15)
C1 C2 C3 N2 -0.1(2)
C1 N1 C4 N3 -179.82(14)
C1 N1 C4 N2 -1.0(2)
C3 N2 C4 N3 -179.31(15)
C3 N2 C4 N1 1.9(2)
C10 C5 C6 C7 0.3(3)
C5 C6 C7 C8 0.3(3)
C6 C7 C8 C9 -0.4(2)
C7 C8 C9 C10 -0.2(2)
C8 C9 C10 C5 0.9(2)
C8 C9 C10 C11 -178.71(14)
C6 C5 C10 C9 -0.9(2)
C6 C5 C10 C11 178.67(15)
C9 C10 C11 O2 -179.79(15)
C5 C10 C11 O2 0.6(2)
C9 C10 C11 O1 0.5(2)
C5 C10 C11 O1 -179.08(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658233
