#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/09/4500949.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_4500949
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-4-nitrobenzoic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.291(3)
_cell_angle_beta                 78.448(3)
_cell_angle_gamma                85.491(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9797(4)
_cell_length_b                   7.3469(4)
_cell_length_c                   13.7131(7)
_cell_measurement_reflns_used    4899
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      34.9
_cell_measurement_theta_min      2.8
_cell_volume                     678.35(6)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_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-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_device_type  'Bruker SMART 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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19134
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         34.86
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.9279
_exptl_absorpt_correction_T_min  0.8482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS ; Bruker, 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Square
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0756P)²+0.2155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1600
_reflns_number_gt                3632
_reflns_number_total             4899
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200539a_si_002.cif
_cod_data_source_block           CP4NBA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4500949
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 0.74627(7) -0.03075(7) 0.76785(3) 0.05417(15) Uani 1 1 d .
N1 N 0.53217(17) 0.23894(17) 0.49448(9) 0.0342(2) Uani 1 1 d .
N3 N 0.78196(17) 0.07517(17) 0.57616(9) 0.0355(3) Uani 1 1 d .
N2 N 0.83935(19) 0.1716(2) 0.40541(10) 0.0457(3) Uani 1 1 d .
H2A H 0.9564 0.1239 0.4028 0.055 Uiso 1 1 calc R
H2B H 0.8023 0.2257 0.3511 0.055 Uiso 1 1 calc R
C9 C 0.3953(2) 0.5514(2) 0.17332(11) 0.0371(3) Uani 1 1 d .
O1 O 0.38112(18) 0.3961(2) 0.33809(9) 0.0540(3) Uani 1 1 d .
H1 H 0.4450 0.3601 0.3823 0.081 Uiso 1 1 calc R
C12 C 0.2098(2) 0.7320(2) 0.02438(11) 0.0413(3) Uani 1 1 d .
C6 C 0.4086(2) 0.2286(2) 0.58327(11) 0.0356(3) Uani 1 1 d .
C4 C 0.6555(2) 0.0716(2) 0.66210(11) 0.0362(3) Uani 1 1 d .
C2 C 0.71521(19) 0.1618(2) 0.49353(10) 0.0334(3) Uani 1 1 d .
O2 O 0.67621(18) 0.4282(2) 0.24009(10) 0.0594(4) Uani 1 1 d .
C8 C 0.4993(2) 0.4521(2) 0.25348(12) 0.0406(3) Uani 1 1 d .
N4 N 0.1085(2) 0.8290(2) -0.05548(11) 0.0534(4) Uani 1 1 d .
C14 C 0.1954(2) 0.5368(2) 0.18180(12) 0.0446(4) Uani 1 1 d .
H14 H 0.1246 0.4663 0.2383 0.053 Uiso 1 1 calc R
C5 C 0.4653(2) 0.1428(2) 0.67197(11) 0.0402(3) Uani 1 1 d .
H5 H 0.3804 0.1340 0.7340 0.048 Uiso 1 1 calc R
C10 C 0.5009(2) 0.6576(3) 0.08940(12) 0.0450(4) Uani 1 1 d .
H10 H 0.6350 0.6660 0.0836 0.054 Uiso 1 1 calc R
C11 C 0.4077(2) 0.7511(3) 0.01414(12) 0.0461(4) Uani 1 1 d .
H11 H 0.4769 0.8248 -0.0417 0.055 Uiso 1 1 calc R
C13 C 0.1012(2) 0.6268(3) 0.10644(13) 0.0481(4) Uani 1 1 d .
H13 H -0.0324 0.6166 0.1111 0.058 Uiso 1 1 calc R
C7 C 0.2049(2) 0.3151(3) 0.58311(14) 0.0454(4) Uani 1 1 d .
H7A H 0.2103 0.4473 0.5723 0.068 Uiso 1 1 calc R
H7B H 0.1220 0.2752 0.6468 0.068 Uiso 1 1 calc R
H7C H 0.1531 0.2778 0.5301 0.068 Uiso 1 1 calc R
O4 O -0.0604(2) 0.7991(3) -0.05104(13) 0.0799(6) Uani 1 1 d .
O3 O 0.1989(3) 0.9366(3) -0.12236(14) 0.0931(7) Uani 1 1 d .
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
C6 N1 C2 117.82(12)
C4 N3 C2 115.28(12)
C2 N2 H2A 120.0
C2 N2 H2B 120.0
H2A N2 H2B 120.0
C10 C9 C14 119.99(14)
C10 C9 C8 119.36(13)
C14 C9 C8 120.65(14)
C8 O1 H1 109.5
C11 C12 C13 122.90(14)
C11 C12 N4 118.83(14)
C13 C12 N4 118.27(14)
N1 C6 C5 121.44(13)
N1 C6 C7 117.21(13)
C5 C6 C7 121.35(14)
N3 C4 C5 125.24(13)
N3 C4 Cl1 114.79(11)
C5 C4 Cl1 119.98(11)
N2 C2 N3 117.24(12)
N2 C2 N1 118.23(12)
N3 C2 N1 124.53(13)
O2 C8 O1 124.24(14)
O2 C8 C9 122.55(15)
O1 C8 C9 113.20(13)
O4 N4 O3 122.89(17)
O4 N4 C12 118.75(15)
O3 N4 C12 118.36(17)
C13 C14 C9 120.18(14)
C13 C14 H14 119.9
C9 C14 H14 119.9
C4 C5 C6 115.67(13)
C4 C5 H5 122.2
C6 C5 H5 122.2
C11 C10 C9 120.43(14)
C11 C10 H10 119.8
C9 C10 H10 119.8
C12 C11 C10 118.06(14)
C12 C11 H11 121.0
C10 C11 H11 121.0
C12 C13 C14 118.43(14)
C12 C13 H13 120.8
C14 C13 H13 120.8
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
Cl1 C4 1.7304(14)
N1 C6 1.3381(19)
N1 C2 1.3548(17)
N3 C4 1.3209(19)
N3 C2 1.3519(17)
N2 C2 1.3331(19)
N2 H2A 0.8600
N2 H2B 0.8600
C9 C10 1.387(2)
C9 C14 1.388(2)
C9 C8 1.494(2)
O1 C8 1.306(2)
O1 H1 0.8200
C12 C11 1.376(2)
C12 C13 1.377(2)
C12 N4 1.475(2)
C6 C5 1.389(2)
C6 C7 1.511(2)
C4 C5 1.377(2)
O2 C8 1.2146(19)
N4 O4 1.204(2)
N4 O3 1.211(2)
C14 C13 1.382(2)
C14 H14 0.9300
C5 H5 0.9300
C10 C11 1.385(2)
C10 H10 0.9300
C11 H11 0.9300
C13 H13 0.9300
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 139144567
