#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/75/4507567.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_4507567
loop_
_publ_author_name
'Cherukuvada, Suryanarayan'
'Bolla, Geetha'
'Sikligar, Kanishka'
'Nangia, Ashwini'
_publ_section_title
;
 4-Aminosalicylic Acid Adducts
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1551
_journal_paper_doi               10.1021/cg301798s
_journal_volume                  13
_journal_year                    2013
_chemical_formula_sum            'C11 H12 N4 O4'
_chemical_formula_weight         264.25
_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                 110.973(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.6069(17)
_cell_length_b                   13.6925(18)
_cell_length_c                   14.595(2)
_cell_measurement_reflns_used    1348
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.12
_cell_measurement_theta_min      2.36
_cell_volume                     2352.5(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1186
_diffrn_reflns_av_sigmaI/netI    0.0933
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24058
_diffrn_reflns_theta_full        26.10
_diffrn_reflns_theta_max         26.10
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         4667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0856
_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)+(0.0344P)²+1.5667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1556
_reflns_number_gt                3233
_reflns_number_total             4667
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301798s_si_002.cif
_cod_data_source_block           Cytosinium-4-Aminosalicylate
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4507567
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
C1 C 0.5899(3) 0.6239(3) 0.9899(3) 0.0211(9) Uani 1 1 d .
C2 C 0.5830(3) 0.6439(2) 0.8890(3) 0.0180(8) Uani 1 1 d .
C3 C 0.6819(3) 0.6514(3) 0.8659(3) 0.0201(8) Uani 1 1 d .
C4 C 0.6768(3) 0.6642(3) 0.7711(3) 0.0221(9) Uani 1 1 d .
H4 H 0.7447 0.6702 0.7575 0.027 Uiso 1 1 calc R
C5 C 0.5722(3) 0.6684(3) 0.6954(3) 0.0213(8) Uani 1 1 d .
C6 C 0.4727(3) 0.6639(3) 0.7166(3) 0.0219(9) Uani 1 1 d .
H6 H 0.4007 0.6695 0.6653 0.026 Uiso 1 1 calc R
C7 C 0.4793(3) 0.6516(3) 0.8110(3) 0.0213(9) Uani 1 1 d .
H7 H 0.4109 0.6481 0.8244 0.026 Uiso 1 1 calc R
C8 C 1.0084(3) 0.0164(3) 0.8845(3) 0.0206(9) Uani 1 1 d .
C9 C 0.9810(3) 0.1207(3) 0.8668(2) 0.0195(8) Uani 1 1 d .
C10 C 1.0595(3) 0.1887(3) 0.8565(3) 0.0222(9) Uani 1 1 d .
C11 C 1.0306(3) 0.2856(3) 0.8385(3) 0.0234(9) Uani 1 1 d .
H11 H 1.0845 0.3306 0.8314 0.028 Uiso 1 1 calc R
C12 C 0.9233(3) 0.3183(3) 0.8307(3) 0.0215(9) Uani 1 1 d .
C13 C 0.8454(3) 0.2514(3) 0.8411(3) 0.0230(9) Uani 1 1 d .
H13 H 0.7718 0.2727 0.8362 0.028 Uiso 1 1 calc R
C14 C 0.8743(3) 0.1550(3) 0.8583(3) 0.0225(9) Uani 1 1 d .
H14 H 0.8198 0.1103 0.8646 0.027 Uiso 1 1 calc R
C15 C 0.2575(3) 0.7666(3) 0.9318(3) 0.0202(8) Uani 1 1 d .
C16 C 0.0669(3) 0.7283(3) 0.9215(3) 0.0203(8) Uani 1 1 d .
C17 C 0.0968(3) 0.6281(3) 0.9358(3) 0.0263(9) Uani 1 1 d .
H17 H 0.0421 0.5802 0.9353 0.032 Uiso 1 1 calc R
C18 C 0.2035(3) 0.6028(3) 0.9498(3) 0.0272(9) Uani 1 1 d .
H18 H 0.2257 0.5363 0.9622 0.033 Uiso 1 1 calc R
C19 C 0.5610(3) 0.4138(3) 0.7684(3) 0.0238(9) Uani 1 1 d .
C20 C 0.3584(3) 0.4290(3) 0.7248(3) 0.0208(8) Uani 1 1 d .
C21 C 0.3450(3) 0.4396(3) 0.6245(3) 0.0258(9) Uani 1 1 d .
H21 H 0.2725 0.4510 0.5756 0.031 Uiso 1 1 calc R
C22 C 0.4375(3) 0.4328(3) 0.6012(3) 0.0281(9) Uani 1 1 d .
H22 H 0.4298 0.4375 0.5342 0.034 Uiso 1 1 calc R
H3 H 0.772(4) 0.636(4) 0.999(4) 0.079(17) Uiso 1 1 d .
H1A H 0.509(3) 0.698(3) 0.558(3) 0.032(12) Uiso 1 1 d .
H2A H 0.820(4) 0.427(3) 0.809(3) 0.044(13) Uiso 1 1 d .
H3A H 0.358(3) 0.649(3) 0.962(3) 0.042(12) Uiso 1 1 d .
H4A H 0.129(3) 0.862(3) 0.910(3) 0.050(14) Uiso 1 1 d .
H5A H -0.046(4) 0.835(4) 0.906(3) 0.068(16) Uiso 1 1 d .
H6A H 1.161(4) 0.085(4) 0.880(4) 0.09(2) Uiso 1 1 d .
H6B H 0.601(4) 0.407(3) 0.654(3) 0.046(14) Uiso 1 1 d .
H7A H 0.475(3) 0.409(3) 0.855(3) 0.022(11) Uiso 1 1 d .
H8A H 0.288(4) 0.419(3) 0.828(4) 0.063(15) Uiso 1 1 d .
H1B H 0.632(3) 0.702(3) 0.590(3) 0.031(11) Uiso 1 1 d .
H2B H 0.923(3) 0.451(3) 0.782(3) 0.038(13) Uiso 1 1 d .
H5B H -0.084(3) 0.723(3) 0.918(3) 0.034(12) Uiso 1 1 d .
H8B H 0.203(4) 0.436(3) 0.711(3) 0.060(15) Uiso 1 1 d .
N1 N 0.5688(3) 0.6731(3) 0.5992(3) 0.0271(8) Uani 1 1 d .
N2 N 0.8958(3) 0.4165(3) 0.8186(3) 0.0284(8) Uani 1 1 d .
N3 N 0.2817(3) 0.6705(2) 0.9467(2) 0.0242(8) Uani 1 1 d .
N4 N 0.1474(2) 0.7923(2) 0.9178(2) 0.0195(7) Uani 1 1 d .
N5 N -0.0328(3) 0.7627(3) 0.9115(2) 0.0227(8) Uani 1 1 d .
N6 N 0.5425(3) 0.4195(2) 0.6699(2) 0.0258(8) Uani 1 1 d .
N7 N 0.4648(3) 0.4160(2) 0.7908(2) 0.0211(7) Uani 1 1 d .
N8 N 0.2744(3) 0.4320(2) 0.7568(3) 0.0251(8) Uani 1 1 d .
O1 O 0.68918(19) 0.61655(19) 1.05570(18) 0.0242(6) Uani 1 1 d .
O2 O 0.50220(19) 0.61464(17) 1.01112(18) 0.0220(6) Uani 1 1 d .
O3 O 0.7872(2) 0.64752(19) 0.93709(19) 0.0258(7) Uani 1 1 d .
O4 O 1.1091(2) -0.01171(19) 0.89493(19) 0.0276(7) Uani 1 1 d .
O5 O 0.9335(2) -0.04223(18) 0.88785(18) 0.0245(6) Uani 1 1 d .
O6 O 1.1667(2) 0.1602(2) 0.8669(2) 0.0287(7) Uani 1 1 d .
O7 O 0.3293(2) 0.82792(18) 0.93317(19) 0.0250(6) Uani 1 1 d .
O8 O 0.6558(2) 0.40755(19) 0.8307(2) 0.0286(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'
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
O2 C1 O1 121.2(3)
O2 C1 C2 121.6(3)
O1 C1 C2 117.2(3)
C7 C2 C3 116.8(3)
C7 C2 C1 122.2(3)
C3 C2 C1 121.0(3)
O3 C3 C4 117.1(3)
O3 C3 C2 121.3(3)
C4 C3 C2 121.6(3)
C3 C4 C5 119.9(3)
C4 C5 N1 119.0(3)
C4 C5 C6 119.7(4)
N1 C5 C6 121.3(4)
C7 C6 C5 119.7(3)
C6 C7 C2 122.3(3)
O5 C8 O4 122.0(3)
O5 C8 C9 119.8(3)
O4 C8 C9 118.2(3)
C14 C9 C10 117.6(3)
C14 C9 C8 120.3(3)
C10 C9 C8 122.1(3)
O6 C10 C11 118.8(3)
O6 C10 C9 120.5(3)
C11 C10 C9 120.7(3)
C10 C11 C12 120.6(3)
N2 C12 C11 121.0(4)
N2 C12 C13 120.0(3)
C11 C12 C13 118.9(3)
C14 C13 C12 120.2(3)
C13 C14 C9 122.0(3)
O7 C15 N3 122.7(3)
O7 C15 N4 121.7(3)
N3 C15 N4 115.6(3)
N5 C16 N4 117.9(3)
N5 C16 C17 124.3(4)
N4 C16 C17 117.8(3)
C18 C17 C16 118.4(4)
C17 C18 N3 121.3(4)
O8 C19 N7 122.7(4)
O8 C19 N6 122.6(3)
N7 C19 N6 114.7(4)
N8 C20 N7 118.3(4)
N8 C20 C21 123.8(4)
N7 C20 C21 117.9(3)
C22 C21 C20 117.7(4)
C21 C22 N6 122.3(4)
C15 N3 C18 122.9(3)
C16 N4 C15 123.9(3)
C22 N6 C19 122.4(3)
C20 N7 C19 124.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.256(4)
C1 O1 1.280(4)
C1 C2 1.470(5)
C2 C7 1.398(5)
C2 C3 1.407(5)
C3 O3 1.363(4)
C3 C4 1.372(5)
C4 C5 1.386(5)
C5 N1 1.390(5)
C5 C6 1.397(5)
C6 C7 1.362(5)
C8 O5 1.254(4)
C8 O4 1.283(4)
C8 C9 1.469(5)
C9 C14 1.387(5)
C9 C10 1.406(5)
C10 O6 1.362(4)
C10 C11 1.377(5)
C11 C12 1.390(5)
C12 N2 1.384(5)
C12 C13 1.391(5)
C13 C14 1.369(5)
C15 O7 1.230(4)
C15 N3 1.351(5)
C15 N4 1.374(4)
C16 N5 1.301(4)
C16 N4 1.358(4)
C16 C17 1.418(5)
C17 C18 1.332(5)
C18 N3 1.365(5)
C19 O8 1.218(4)
C19 N7 1.365(4)
C19 N6 1.374(5)
C20 N8 1.302(4)
C20 N7 1.354(4)
C20 C21 1.420(5)
C21 C22 1.329(5)
C22 N6 1.356(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146441
