#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/09/4500953.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4500953
loop_
_publ_author_name
'Ebenezer, Samuel'
'Muthiah, P. Thomas'
'Butcher, Ray J.'
_publ_section_title
;
 Design of a Series of Isostructural Co-Crystals with Aminopyrimidines:
 Isostructurality through Chloro/Methyl Exchange and Studies on
 Supramolecular Architectures
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3579
_journal_paper_doi               10.1021/cg200539a
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C7 H5 N O4, C5 H6 Cl N3'
_chemical_formula_sum            'C12 H11 Cl N4 O4'
_chemical_formula_weight         310.70
_chemical_name_systematic
;
 2-amino-4-chloro-6-methylpyrimidine-3-nitrobenzoic acid
;
_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                 121.196(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8924(3)
_cell_length_b                   15.0036(4)
_cell_length_c                   11.3404(4)
_cell_measurement_reflns_used    1942
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.7
_cell_measurement_theta_min      2.4
_cell_volume                     1439.78(8)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'SMART APEX II (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'Mercury 2.2 (Macrae et al., 2006)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX II 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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10187
_diffrn_reflns_theta_full        22.74
_diffrn_reflns_theta_max         22.74
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Bruker, 2008)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0775P)²+0.4391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1363
_reflns_number_gt                1495
_reflns_number_total             1942
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200539a_si_002.cif
_cod_data_source_block           CP3NBA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4500953
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.3235(2) 0.33350(12) 0.25213(18) 0.0671(6) Uani 1 1 d .
H1 H 0.3663 0.2989 0.3175 0.101 Uiso 1 1 d R
O2 O 0.2358(2) 0.20770(12) 0.13107(18) 0.0754(6) Uani 1 1 d .
O3 O 0.1886(3) 0.61588(13) 0.0170(3) 0.0806(7) Uani 1 1 d .
O4 O 0.0359(3) 0.62289(14) -0.2016(2) 0.0958(8) Uani 1 1 d .
N4 N 0.1087(3) 0.58154(15) -0.0951(3) 0.0616(6) Uani 1 1 d .
C8 C 0.2441(3) 0.28813(17) 0.1372(3) 0.0547(7) Uani 1 1 d .
C9 C 0.1638(3) 0.34393(15) 0.0107(2) 0.0484(6) Uani 1 1 d .
C10 C 0.1754(3) 0.43628(16) 0.0172(3) 0.0480(6) Uani 1 1 d .
H10 H 0.2342 0.4653 0.1015 0.058 Uiso 1 1 calc R
C11 C 0.0984(3) 0.48340(15) -0.1029(2) 0.0492(6) Uani 1 1 d .
C12 C 0.0113(3) 0.44329(19) -0.2294(3) 0.0625(7) Uani 1 1 d .
H12 H -0.0406 0.4772 -0.3094 0.075 Uiso 1 1 calc R
C13 C 0.0023(3) 0.35224(19) -0.2352(3) 0.0681(8) Uani 1 1 d .
H13 H -0.0549 0.3236 -0.3199 0.082 Uiso 1 1 calc R
C14 C 0.0777(3) 0.30336(18) -0.1159(3) 0.0600(7) Uani 1 1 d .
H14 H 0.0704 0.2415 -0.1206 0.072 Uiso 1 1 calc R
Cl1 Cl 0.75101(12) 0.08874(6) 0.87353(8) 0.0988(4) Uani 1 1 d .
N1 N 0.4826(2) 0.23781(13) 0.4832(2) 0.0520(5) Uani 1 1 d .
N2 N 0.4234(3) 0.10183(13) 0.3745(2) 0.0593(6) Uani 1 1 d .
H2A H 0.4293 0.0446 0.3763 0.071 Uiso 1 1 d R
H2B H 0.3704 0.1293 0.2969 0.071 Uiso 1 1 d R
N3 N 0.5771(2) 0.10131(12) 0.6089(2) 0.0522(6) Uani 1 1 d .
C2 C 0.4960(3) 0.14764(15) 0.4909(2) 0.0486(6) Uani 1 1 d .
C4 C 0.6474(3) 0.14898(18) 0.7226(3) 0.0581(7) Uani 1 1 d .
C5 C 0.6418(3) 0.24035(18) 0.7269(3) 0.0651(8) Uani 1 1 d .
H5 H 0.6933 0.2716 0.8097 0.078 Uiso 1 1 calc R
C6 C 0.5557(3) 0.28287(17) 0.6021(3) 0.0567(7) Uani 1 1 d .
C7 C 0.5388(4) 0.38567(16) 0.5921(3) 0.0657(8) Uani 1 1 d .
H7A H 0.4317 0.4017 0.5620 0.099 Uiso 1 1 calc R
H7B H 0.5654 0.4075 0.5271 0.099 Uiso 1 1 calc R
H7C H 0.6086 0.4115 0.6809 0.099 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 O1 H1 109.5
O4 N4 O3 123.9(2)
O4 N4 C11 117.7(2)
O3 N4 C11 118.4(2)
O2 C8 O1 124.3(2)
O2 C8 C9 121.4(2)
O1 C8 C9 114.4(2)
C14 C9 C10 119.1(2)
C14 C9 C8 119.4(2)
C10 C9 C8 121.5(2)
C11 C10 C9 118.4(2)
C11 C10 H10 120.8
C9 C10 H10 120.8
C10 C11 C12 122.7(2)
C10 C11 N4 118.1(2)
C12 C11 N4 119.2(2)
C13 C12 C11 118.6(2)
C13 C12 H12 120.7
C11 C12 H12 120.7
C12 C13 C14 119.9(2)
C12 C13 H13 120.1
C14 C13 H13 120.1
C13 C14 C9 121.3(2)
C13 C14 H14 119.3
C9 C14 H14 119.3
C6 N1 C2 117.1(2)
C2 N2 H2A 120.0
C2 N2 H2B 120.0
H2A N2 H2B 120.0
C4 N3 C2 115.8(2)
N2 C2 N3 117.4(2)
N2 C2 N1 118.0(2)
N3 C2 N1 124.5(2)
N3 C4 C5 124.6(2)
N3 C4 Cl1 115.4(2)
C5 C4 Cl1 120.1(2)
C6 C5 C4 116.2(2)
C6 C5 H5 121.9
C4 C5 H5 121.9
N1 C6 C5 121.8(2)
N1 C6 C7 116.6(2)
C5 C6 C7 121.6(2)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.311(3)
O1 H1 0.8200
O2 C8 1.209(3)
O3 N4 1.210(3)
O4 N4 1.209(3)
N4 C11 1.475(3)
C8 C9 1.486(3)
C9 C14 1.375(3)
C9 C10 1.389(3)
C10 C11 1.364(3)
C10 H10 0.9300
C11 C12 1.371(4)
C12 C13 1.368(4)
C12 H12 0.9300
C13 C14 1.371(4)
C13 H13 0.9300
C14 H14 0.9300
Cl1 C4 1.726(3)
N1 C6 1.337(3)
N1 C2 1.358(3)
N2 C2 1.322(3)
N2 H2A 0.8600
N2 H2B 0.8600
N3 C4 1.314(3)
N3 C2 1.344(3)
C4 C5 1.374(4)
C5 C6 1.374(4)
C5 H5 0.9300
C6 C7 1.549(3)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144570
