#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/75/4507570.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_4507570
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            'C13 H15 N3 O5'
_chemical_formula_weight         293.28
_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                95.977(4)
_cell_angle_beta                 97.899(5)
_cell_angle_gamma                104.722(4)
_cell_formula_units_Z            2
_cell_length_a                   6.750(2)
_cell_length_b                   7.060(2)
_cell_length_c                   14.809(4)
_cell_measurement_reflns_used    2692
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      2.81
_cell_volume                     668.9(3)
_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 0.941
_diffrn_measured_fraction_theta_max 0.941
_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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5351
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_correction_T_min  0.9602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0400
_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)+(0.0703P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                1653
_reflns_number_total             2206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301798s_si_005.cif
_cod_data_source_block           4-Aminosalicylic-acid-Nicotinamide-Hydrate
_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 2.4.2 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      P-1
_cod_database_code               4507570
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
C1 C 0.2238(2) 0.5722(2) 0.90594(12) 0.0185(4) Uani 1 1 d .
C2 C 0.2307(2) 0.6927(2) 0.83216(11) 0.0171(4) Uani 1 1 d .
C3 C 0.1716(2) 0.6005(2) 0.73924(12) 0.0179(4) Uani 1 1 d .
C4 C 0.1750(2) 0.7091(2) 0.66764(12) 0.0194(4) Uani 1 1 d .
H4 H 0.1349 0.6433 0.6060 0.023 Uiso 1 1 calc R
C5 C 0.2372(2) 0.9162(2) 0.68477(12) 0.0198(4) Uani 1 1 d .
C6 C 0.2971(2) 1.0095(2) 0.77686(11) 0.0196(4) Uani 1 1 d .
H6 H 0.3401 1.1499 0.7898 0.024 Uiso 1 1 calc R
C7 C 0.2940(2) 0.8997(2) 0.84780(12) 0.0189(4) Uani 1 1 d .
H7 H 0.3359 0.9659 0.9094 0.023 Uiso 1 1 calc R
C8 C 0.3769(2) 0.3987(2) 0.36144(11) 0.0182(4) Uani 1 1 d .
C9 C 0.3110(2) 0.3223(2) 0.26118(11) 0.0167(4) Uani 1 1 d .
C10 C 0.3154(2) 0.4592(2) 0.20001(12) 0.0189(4) Uani 1 1 d .
H10 H 0.3539 0.5957 0.2246 0.023 Uiso 1 1 calc R
C11 C 0.2134(2) 0.2159(2) 0.07461(12) 0.0202(4) Uani 1 1 d .
H11 H 0.1816 0.1781 0.0097 0.024 Uiso 1 1 calc R
C12 C 0.2014(2) 0.0705(2) 0.13006(12) 0.0202(4) Uani 1 1 d .
H12 H 0.1600 -0.0651 0.1037 0.024 Uiso 1 1 calc R
C13 C 0.2500(2) 0.1232(2) 0.22459(12) 0.0190(4) Uani 1 1 d .
H13 H 0.2418 0.0245 0.2640 0.023 Uiso 1 1 calc R
H1 H 0.273(3) 0.566(3) 1.0347(18) 0.062(7) Uiso 1 1 d .
H3 H 0.117(3) 0.361(3) 0.7737(16) 0.041(6) Uiso 1 1 d .
H1A H 0.215(3) 0.957(3) 0.5568(15) 0.034(5) Uiso 1 1 d .
H2A H 0.405(3) 0.323(3) 0.4804(15) 0.036(5) Uiso 1 1 d .
H5A H 0.095(3) 0.784(3) 0.3860(15) 0.039(6) Uiso 1 1 d .
H1B H 0.291(3) 1.144(3) 0.6270(15) 0.043(6) Uiso 1 1 d .
H2B H 0.299(3) 0.134(3) 0.4025(14) 0.036(5) Uiso 1 1 d .
H5B H 0.286(4) 0.771(4) 0.4088(19) 0.073(10) Uiso 1 1 d .
N1 N 0.2359(2) 1.0246(2) 0.61406(11) 0.0260(4) Uani 1 1 d .
N2 N 0.3554(2) 0.2715(2) 0.42102(11) 0.0221(4) Uani 1 1 d .
N3 N 0.26852(18) 0.40941(18) 0.10860(9) 0.0191(3) Uani 1 1 d .
O1 O 0.28403(17) 0.66631(16) 0.99055(8) 0.0231(3) Uani 1 1 d .
O2 O 0.16349(16) 0.38828(15) 0.89001(8) 0.0237(3) Uani 1 1 d .
O3 O 0.11136(17) 0.39964(16) 0.71924(9) 0.0232(3) Uani 1 1 d .
O4 O 0.45210(17) 0.58011(15) 0.38700(8) 0.0235(3) Uani 1 1 d .
O5 O 0.2123(2) 0.84748(18) 0.41641(9) 0.0269(3) 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 121.39(15)
O2 C1 C2 121.69(15)
O1 C1 C2 116.92(14)
C7 C2 C3 117.10(15)
C7 C2 C1 123.09(15)
C3 C2 C1 119.80(14)
O3 C3 C4 118.36(15)
O3 C3 C2 120.06(15)
C4 C3 C2 121.57(14)
C3 C4 C5 120.45(15)
C3 C4 H4 119.8
C5 C4 H4 119.8
N1 C5 C4 120.66(16)
N1 C5 C6 120.84(15)
C4 C5 C6 118.49(15)
C7 C6 C5 120.58(15)
C7 C6 H6 119.7
C5 C6 H6 119.7
C6 C7 C2 121.81(15)
C6 C7 H7 119.1
C2 C7 H7 119.1
O4 C8 N2 121.62(15)
O4 C8 C9 119.58(14)
N2 C8 C9 118.80(14)
C13 C9 C10 117.67(16)
C13 C9 C8 124.30(15)
C10 C9 C8 118.01(13)
N3 C10 C9 123.61(14)
N3 C10 H10 118.2
C9 C10 H10 118.2
N3 C11 C12 122.58(16)
N3 C11 H11 118.7
C12 C11 H11 118.7
C11 C12 C13 119.36(15)
C11 C12 H12 120.3
C13 C12 H12 120.3
C12 C13 C9 119.06(15)
C12 C13 H13 120.5
C9 C13 H13 120.5
C5 N1 H1A 116.4(12)
C5 N1 H1B 116.6(15)
H1A N1 H1B 124(2)
C8 N2 H2A 115.8(12)
C8 N2 H2B 122.3(12)
H2A N2 H2B 121.8(17)
C10 N3 C11 117.69(14)
C1 O1 H1 108.9(14)
C3 O3 H3 103.4(14)
H5A O5 H5B 104(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.2447(18)
C1 O1 1.314(2)
C1 C2 1.451(2)
C2 C7 1.399(2)
C2 C3 1.417(2)
C3 O3 1.3604(19)
C3 C4 1.371(2)
C4 C5 1.400(2)
C4 H4 0.9500
C5 N1 1.360(2)
C5 C6 1.408(2)
C6 C7 1.368(2)
C6 H6 0.9500
C7 H7 0.9500
C8 O4 1.2480(18)
C8 N2 1.319(2)
C8 C9 1.491(2)
C9 C13 1.387(2)
C9 C10 1.389(2)
C10 N3 1.335(2)
C10 H10 0.9500
C11 N3 1.344(2)
C11 C12 1.373(2)
C11 H11 0.9500
C12 C13 1.382(2)
C12 H12 0.9500
C13 H13 0.9500
N1 H1A 0.90(2)
N1 H1B 0.82(2)
N2 H2A 0.90(2)
N2 H2B 0.94(2)
O1 H1 1.01(3)
O3 H3 0.88(2)
O5 H5A 0.84(2)
O5 H5B 0.84(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652525
2 PubChem 139146444
