#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/46/7204664.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_7204664
loop_
_publ_author_name
'Vishweshwar, Peddy'
'Nangia, Ashwini'
'Lynch, Vincent M.'
_publ_section_title
;
 Supramolecular synthons in phenol?isonicotinamide adducts
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              164
_journal_paper_doi               10.1039/b304078j
_journal_volume                  5
_journal_year                    2003
_chemical_formula_moiety         '2(C6 H6 N2 O), C6 H6 O3, 2(H2 O)'
_chemical_formula_sum            'C18 H22 N4 O7'
_chemical_formula_weight         406.40
_chemical_melting_point          417
_chemical_name_common
'1:2 molecular complex of phloroglucinol and isonicotinamide dihydrate'
_chemical_name_systematic
; 
1:2 molecular complex of phloroglucinol and isonicotinamide dihydrate
;
_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                95.1886(6)
_cell_angle_beta                 97.4790(6)
_cell_angle_gamma                105.7701(7)
_cell_formula_units_Z            2
_cell_length_a                   7.4967(1)
_cell_length_b                   8.8748(1)
_cell_length_c                   15.2793(3)
_cell_measurement_reflns_used    4275
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.91
_cell_volume                     961.50(3)
_computing_cell_refinement       'DENZO-SMN (Z. Otwinowski and W. Minor, 1997)'
_computing_data_collection       'Collect data collection software, Nonius 1998'
_computing_data_reduction        'SCALEPACK (Z. Otwinowski and W. Minor, 1997)'
_computing_molecular_graphics    'PLUTON (Spek, 1992)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal focus for the X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6903
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        'less than 1'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Lathes
_exptl_crystal_F_000             428
_exptl_crystal_preparation       Acetone
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0363
_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)+(0.0481P)²+0.2279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                3583
_reflns_number_total             4275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b304078j.txt
_cod_data_source_block           pgin
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/adriana/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_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '417 K' was changed to '417' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_database_code               7204664
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O28 O 0.82310(11) 0.33498(10) 0.12632(6) 0.02310(19) Uani 1 1 d . . .
N17 N 0.77754(13) 0.24287(11) -0.05698(6) 0.0221(2) Uani 1 1 d . . .
O29 O 0.44715(12) 0.41768(10) 0.34461(5) 0.0260(2) Uani 1 1 d . . .
O27 O 0.16483(12) 0.27472(11) 0.04359(6) 0.0277(2) Uani 1 1 d . . .
N8 N 0.21727(14) 0.14953(12) -0.11954(6) 0.0235(2) Uani 1 1 d . . .
O20 O 0.82756(14) 0.21482(10) -0.38149(6) 0.0310(2) Uani 1 1 d . . .
O11 O 0.27206(14) 0.10941(10) -0.44248(6) 0.0323(2) Uani 1 1 d . . .
C22 C 0.49540(16) 0.30644(13) 0.08086(7) 0.0196(2) Uani 1 1 d . . .
N19 N 0.68935(17) -0.04012(13) -0.37208(7) 0.0298(3) Uani 1 1 d . . .
C24 C 0.64078(16) 0.37610(13) 0.23602(7) 0.0197(2) Uani 1 1 d . . .
C5 C 0.21427(16) 0.04926(13) -0.29857(7) 0.0202(2) Uani 1 1 d . . .
C25 C 0.46818(16) 0.38268(12) 0.25757(7) 0.0191(2) Uani 1 1 d . . .
C26 C 0.30858(16) 0.35001(13) 0.19337(7) 0.0205(2) Uani 1 1 d . . .
N10 N 0.15482(16) -0.14763(12) -0.42908(7) 0.0287(2) Uani 1 1 d . . .
C14 C 0.76239(15) 0.15215(13) -0.23865(7) 0.0194(2) Uani 1 1 d . . .
C23 C 0.65303(15) 0.33843(12) 0.14674(7) 0.0184(2) Uani 1 1 d . . .
C13 C 0.85872(17) 0.30424(14) -0.19887(8) 0.0231(2) Uani 1 1 d . . .
C12 C 0.86142(17) 0.34459(14) -0.10875(8) 0.0239(3) Uani 1 1 d . . .
C9 C 0.21465(16) 0.00442(14) -0.39615(7) 0.0227(2) Uani 1 1 d . . .
C15 C 0.67262(17) 0.04606(14) -0.18568(8) 0.0229(2) Uani 1 1 d . . .
C18 C 0.76121(16) 0.11042(13) -0.33671(7) 0.0214(2) Uani 1 1 d . . .
C7 C 0.12688(17) 0.00103(14) -0.15612(8) 0.0238(3) Uani 1 1 d . . .
C6 C 0.12332(17) -0.05406(14) -0.24471(8) 0.0232(2) Uani 1 1 d . . .
C21 C 0.32361(16) 0.31000(13) 0.10491(7) 0.0200(2) Uani 1 1 d . . .
C16 C 0.68492(17) 0.09631(14) -0.09564(8) 0.0243(3) Uani 1 1 d . . .
C4 C 0.31010(17) 0.20303(14) -0.26045(8) 0.0238(3) Uani 1 1 d . . .
C3 C 0.30868(18) 0.24737(14) -0.17138(8) 0.0256(3) Uani 1 1 d . . .
O2 O 0.77121(14) 0.58461(11) 0.43841(6) 0.0322(2) Uani 1 1 d . . .
O1 O 0.10642(14) 0.45000(11) 0.38567(6) 0.0281(2) Uani 1 1 d . . .
H22 H 0.505(2) 0.2795(16) 0.0176(10) 0.028(4) Uiso 1 1 d . . .
H7 H 0.0645(19) -0.0681(16) -0.1181(9) 0.025(3) Uiso 1 1 d . . .
H12 H 0.925(2) 0.4480(18) -0.0804(10) 0.031(4) Uiso 1 1 d . . .
H15 H 0.603(2) -0.0610(18) -0.2070(10) 0.030(4) Uiso 1 1 d . . .
H4 H 0.375(2) 0.2771(17) -0.2945(10) 0.030(4) Uiso 1 1 d . . .
H3 H 0.374(2) 0.3510(19) -0.1435(10) 0.037(4) Uiso 1 1 d . . .
H19B H 0.693(2) -0.0624(19) -0.4309(12) 0.041(4) Uiso 1 1 d . . .
H27 H 0.190(2) 0.230(2) -0.0114(12) 0.051(5) Uiso 1 1 d . . .
H16 H 0.625(2) 0.0212(18) -0.0585(9) 0.029(4) Uiso 1 1 d . . .
H26 H 0.190(2) 0.3548(16) 0.2094(9) 0.027(3) Uiso 1 1 d . . .
H10B H 0.155(2) -0.1712(18) -0.4890(12) 0.040(4) Uiso 1 1 d . . .
H6 H 0.055(2) -0.1626(18) -0.2655(10) 0.031(4) Uiso 1 1 d . . .
H13 H 0.927(2) 0.3803(18) -0.2327(10) 0.033(4) Uiso 1 1 d . . .
H24 H 0.753(2) 0.3994(16) 0.2804(9) 0.026(3) Uiso 1 1 d . . .
H10A H 0.107(2) -0.222(2) -0.3973(11) 0.039(4) Uiso 1 1 d . . .
H28 H 0.807(2) 0.304(2) 0.0659(12) 0.048(5) Uiso 1 1 d . . .
H19A H 0.650(2) -0.114(2) -0.3386(11) 0.042(4) Uiso 1 1 d . . .
H1A H 0.098(2) 0.547(2) 0.3821(12) 0.050(5) Uiso 1 1 d . . .
H2A H 0.764(3) 0.684(3) 0.4398(13) 0.062(6) Uiso 1 1 d . . .
H29 H 0.560(3) 0.468(2) 0.3778(12) 0.055(5) Uiso 1 1 d . . .
H1B H 0.218(3) 0.448(2) 0.3684(13) 0.061(6) Uiso 1 1 d . . .
H2B H 0.808(3) 0.572(2) 0.4921(15) 0.063(6) Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N17 C16 117.29(10) . . ?
C7 N8 C3 117.63(10) . . ?
C21 C22 C23 119.41(10) . . ?
C25 C24 C23 118.40(10) . . ?
C6 C5 C4 118.10(11) . . ?
C6 C5 C9 123.77(10) . . ?
C4 C5 C9 118.13(11) . . ?
O29 C25 C26 116.96(10) . . ?
O29 C25 C24 120.99(10) . . ?
C26 C25 C24 122.02(10) . . ?
C25 C26 C21 118.52(10) . . ?
C13 C14 C15 117.99(10) . . ?
C13 C14 C18 118.45(10) . . ?
C15 C14 C18 123.56(10) . . ?
O28 C23 C22 121.37(10) . . ?
O28 C23 C24 117.86(10) . . ?
C22 C23 C24 120.76(10) . . ?
C14 C13 C12 119.21(11) . . ?
N17 C12 C13 123.26(11) . . ?
O11 C9 N10 122.31(11) . . ?
O11 C9 C5 119.34(10) . . ?
N10 C9 C5 118.35(10) . . ?
C14 C15 C16 118.85(11) . . ?
O20 C18 N19 121.96(11) . . ?
O20 C18 C14 119.88(10) . . ?
N19 C18 C14 118.15(10) . . ?
N8 C7 C6 122.91(11) . . ?
C5 C6 C7 119.06(11) . . ?
O27 C21 C22 121.64(10) . . ?
O27 C21 C26 117.50(10) . . ?
C22 C21 C26 120.86(10) . . ?
N17 C16 C15 123.39(11) . . ?
C3 C4 C5 119.04(11) . . ?
N8 C3 C4 123.22(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O28 C23 1.3590(14) . ?
N17 C12 1.3364(15) . ?
N17 C16 1.3365(15) . ?
O29 C25 1.3771(13) . ?
O27 C21 1.3590(13) . ?
N8 C7 1.3384(16) . ?
N8 C3 1.3391(16) . ?
O20 C18 1.2357(14) . ?
O11 C9 1.2390(15) . ?
C22 C21 1.3921(16) . ?
C22 C23 1.3952(15) . ?
N19 C18 1.3303(16) . ?
C24 C25 1.3909(16) . ?
C24 C23 1.3956(15) . ?
C5 C6 1.3876(17) . ?
C5 C4 1.3901(16) . ?
C5 C9 1.5085(15) . ?
C25 C26 1.3900(16) . ?
C26 C21 1.3929(15) . ?
N10 C9 1.3284(16) . ?
C14 C13 1.3857(16) . ?
C14 C15 1.3890(17) . ?
C14 C18 1.5089(15) . ?
C13 C12 1.3872(17) . ?
C15 C16 1.3906(17) . ?
C7 C6 1.3914(16) . ?
C4 C3 1.3842(17) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149552
2 PubChem 139195479
