#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/64/4506457.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_4506457
loop_
_publ_author_name
'Thakuria, Ranjit'
'Cherukuvada, Suryanarayan'
'Nangia, Ashwini'
_publ_section_title
;
 Crystal Structures of Pyrogallol, Its Hydrate, and Stable
 MultipleZ′ Cocrystals with N-Heterocycles Containing Metastable
 Conformers of Pyrogallol
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3944
_journal_paper_doi               10.1021/cg3003367
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         ' C6 H6 O3, 0.5(C6 H6 N2 O)'
_chemical_formula_sum            'C18 H18 N2 O7'
_chemical_formula_weight         374.34
_chemical_name_systematic
; 
 2:1 complex of pyrogallol and isonicotinamide 
;
_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                72.4640(10)
_cell_angle_beta                 83.730(2)
_cell_angle_gamma                80.0920(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2540(8)
_cell_length_b                   9.5435(9)
_cell_length_c                   10.0539(9)
_cell_measurement_reflns_used    4061
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.26
_cell_volume                     832.47(13)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8725
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0389
_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)+(0.0478P)²+0.3403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                3022
_reflns_number_total             3277
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3003367_si_006.cif
_cod_data_source_block           Pyrogallol_Isonicotinamide_4b
_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.

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               4506457
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 0.33049(15) 0.73589(16) 0.76767(15) 0.0146(3) Uani 1 1 d .
C2 C 0.19621(15) 0.82570(15) 0.73634(14) 0.0138(3) Uani 1 1 d .
C3 C 0.07174(15) 0.79380(15) 0.82462(15) 0.0144(3) Uani 1 1 d .
C4 C 0.08168(16) 0.67420(16) 0.94520(15) 0.0175(3) Uani 1 1 d .
H4 H -0.0027 0.6540 1.0066 0.021 Uiso 1 1 calc R
C5 C 0.21612(17) 0.58449(16) 0.97516(15) 0.0187(3) Uani 1 1 d .
H5 H 0.2234 0.5024 1.0572 0.022 Uiso 1 1 calc R
C6 C 0.33975(16) 0.61405(16) 0.88603(15) 0.0174(3) Uani 1 1 d .
H6 H 0.4308 0.5509 0.9060 0.021 Uiso 1 1 calc R
C7 C 0.26392(15) 0.42177(15) 0.47783(15) 0.0157(3) Uani 1 1 d .
C8 C 0.17548(15) 0.32446(15) 0.46220(15) 0.0146(3) Uani 1 1 d .
C9 C 0.05993(15) 0.28741(15) 0.56083(15) 0.0146(3) Uani 1 1 d .
C10 C 0.03362(16) 0.34485(16) 0.67367(15) 0.0169(3) Uani 1 1 d .
H10 H -0.0458 0.3194 0.7401 0.020 Uiso 1 1 calc R
C11 C 0.12458(17) 0.44015(16) 0.68887(15) 0.0184(3) Uani 1 1 d .
H11 H 0.1069 0.4801 0.7660 0.022 Uiso 1 1 calc R
C12 C 0.24071(16) 0.47717(16) 0.59232(16) 0.0178(3) Uani 1 1 d .
H12 H 0.3041 0.5402 0.6044 0.021 Uiso 1 1 calc R
C13 C 0.51736(15) 0.85158(15) 0.19954(14) 0.0147(3) Uani 1 1 d .
C14 C 0.64798(16) 0.90400(16) 0.20108(15) 0.0169(3) Uani 1 1 d .
H14 H 0.6651 0.9399 0.2756 0.020 Uiso 1 1 calc R
C15 C 0.75243(16) 0.90286(16) 0.09230(15) 0.0180(3) Uani 1 1 d .
H15 H 0.8416 0.9389 0.0935 0.022 Uiso 1 1 calc R
C16 C 0.60866(16) 0.79974(16) -0.01412(15) 0.0172(3) Uani 1 1 d .
H16 H 0.5952 0.7626 -0.0889 0.021 Uiso 1 1 calc R
C17 C 0.49825(16) 0.79610(16) 0.09079(15) 0.0161(3) Uani 1 1 d .
H17 H 0.4114 0.7566 0.0885 0.019 Uiso 1 1 calc R
C18 C 0.39648(15) 0.85515(15) 0.31168(15) 0.0154(3) Uani 1 1 d .
H1 H 0.509(2) 0.697(2) 0.677(2) 0.037(6) Uiso 1 1 d .
H2 H 0.099(2) 0.994(2) 0.615(2) 0.041(6) Uiso 1 1 d .
H3 H -0.123(2) 0.868(2) 0.849(2) 0.036(5) Uiso 1 1 d .
H1A H 0.320(2) 0.958(2) 0.447(2) 0.025(5) Uiso 1 1 d .
H4A H 0.370(2) 0.557(3) 0.355(2) 0.041(6) Uiso 1 1 d .
H5A H 0.136(2) 0.223(2) 0.345(2) 0.036(6) Uiso 1 1 d .
H6A H -0.109(3) 0.201(2) 0.576(2) 0.044(6) Uiso 1 1 d .
H1B H 0.446(2) 1.034(2) 0.342(2) 0.032(5) Uiso 1 1 d .
N1 N 0.38594(14) 0.96095(14) 0.37239(13) 0.0178(3) Uani 1 1 d .
N2 N 0.73370(13) 0.85312(13) -0.01527(13) 0.0176(3) Uani 1 1 d .
O1 O 0.44995(11) 0.77580(12) 0.67909(11) 0.0181(2) Uani 1 1 d .
O2 O 0.18901(11) 0.94548(11) 0.61931(10) 0.0150(2) Uani 1 1 d .
O3 O -0.05524(11) 0.88562(11) 0.78147(11) 0.0178(2) Uani 1 1 d .
O4 O 0.37237(11) 0.46260(12) 0.37369(12) 0.0214(3) Uani 1 1 d .
O5 O 0.20247(12) 0.27381(12) 0.34714(11) 0.0195(2) Uani 1 1 d .
O6 O -0.02371(11) 0.19116(11) 0.53761(11) 0.0166(2) Uani 1 1 d .
O7 O 0.31058(11) 0.76092(11) 0.34165(11) 0.0201(2) 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
O1 C1 C6 123.02(13)
O1 C1 C2 117.05(13)
C6 C1 C2 119.91(13)
O2 C2 C1 119.18(12)
O2 C2 C3 121.02(13)
C1 C2 C3 119.80(13)
O3 C3 C4 124.65(13)
O3 C3 C2 115.01(12)
C4 C3 C2 120.33(13)
C5 C4 C3 119.44(13)
C6 C5 C4 120.41(14)
C5 C6 C1 120.06(13)
O4 C7 C12 122.06(13)
O4 C7 C8 117.31(13)
C12 C7 C8 120.61(13)
O5 C8 C7 118.27(13)
O5 C8 C9 122.73(13)
C7 C8 C9 118.95(13)
O6 C9 C10 123.54(13)
O6 C9 C8 115.57(12)
C10 C9 C8 120.89(13)
C9 C10 C11 119.39(13)
C12 C11 C10 120.44(14)
C11 C12 C7 119.67(13)
C14 C13 C17 118.91(13)
C14 C13 C18 121.49(13)
C17 C13 C18 119.61(13)
C15 C14 C13 118.68(13)
N2 C15 C14 122.97(14)
N2 C16 C17 123.11(13)
C16 C17 C13 118.45(13)
O7 C18 N1 123.22(13)
O7 C18 C13 119.67(13)
N1 C18 C13 117.10(12)
C16 N2 C15 117.84(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.3733(17)
C1 C6 1.389(2)
C1 C2 1.391(2)
C2 O2 1.3697(17)
C2 C3 1.3935(19)
C3 O3 1.3656(17)
C3 C4 1.391(2)
C4 C5 1.390(2)
C5 C6 1.388(2)
C7 O4 1.3836(17)
C7 C12 1.387(2)
C7 C8 1.391(2)
C8 O5 1.3663(17)
C8 C9 1.392(2)
C9 O6 1.3823(17)
C9 C10 1.384(2)
C10 C11 1.391(2)
C11 C12 1.385(2)
C13 C14 1.389(2)
C13 C17 1.389(2)
C13 C18 1.5027(19)
C14 C15 1.380(2)
C15 N2 1.3430(19)
C16 N2 1.3397(19)
C16 C17 1.383(2)
C18 O7 1.2497(17)
C18 N1 1.3138(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652464
2 PubChem 139146118
