#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/64/4506455.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_4506455
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, C5 H5 N3 O'
_chemical_formula_sum            'C11 H11 N3 O4'
_chemical_formula_weight         249.23
_chemical_name_systematic
; 
 1:1 complex of pyrogallol and pyrazinamide 
;
_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                80.61(2)
_cell_angle_beta                 87.92(2)
_cell_angle_gamma                76.02(2)
_cell_formula_units_Z            2
_cell_length_a                   6.687(9)
_cell_length_b                   7.074(9)
_cell_length_c                   11.721(16)
_cell_measurement_reflns_used    1098
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      3.01
_cell_volume                     530.8(12)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0658
_diffrn_reflns_av_sigmaI/netI    0.0796
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4997
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.9599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0779
_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)+(0.1154P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2035
_refine_ls_wR_factor_ref         0.2176
_reflns_number_gt                1422
_reflns_number_total             1859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3003367_si_004.cif
_cod_data_source_block           Pyrogallol_Pyrazinamide
_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               4506455
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 0.2359(5) 0.7684(5) 0.6864(3) 0.0179(8) Uani 1 1 d .
C2 C 0.2005(5) 0.9404(5) 0.7344(3) 0.0181(8) Uani 1 1 d .
C3 C 0.2096(5) 0.9274(5) 0.8541(3) 0.0180(8) Uani 1 1 d .
C4 C 0.2497(6) 0.7438(5) 0.9231(3) 0.0232(9) Uani 1 1 d .
H4 H 0.2526 0.7339 1.0049 0.028 Uiso 1 1 calc R
C5 C 0.2858(5) 0.5746(5) 0.8729(3) 0.0211(9) Uani 1 1 d .
H5 H 0.3154 0.4490 0.9207 0.025 Uiso 1 1 calc R
C6 C 0.2792(5) 0.5857(5) 0.7546(3) 0.0232(9) Uani 1 1 d .
H6 H 0.3041 0.4691 0.7207 0.028 Uiso 1 1 calc R
C7 C 0.7469(5) 0.7609(5) 0.7062(3) 0.0192(8) Uani 1 1 d .
C8 C 0.7606(5) 0.7531(5) 0.8244(3) 0.0180(8) Uani 1 1 d .
H8 H 0.8035 0.6285 0.8723 0.022 Uiso 1 1 calc R
C9 C 0.6499(5) 1.0852(5) 0.8011(3) 0.0203(8) Uani 1 1 d .
H9 H 0.6092 1.2044 0.8324 0.024 Uiso 1 1 calc R
C10 C 0.6395(5) 1.0934(5) 0.6826(3) 0.0192(8) Uani 1 1 d .
H10 H 0.5958 1.2181 0.6350 0.023 Uiso 1 1 calc R
C11 C 0.7986(5) 0.5725(5) 0.6566(3) 0.0175(8) Uani 1 1 d .
H1 H 0.212(8) 0.893(8) 0.542(5) 0.062(18) Uiso 1 1 d .
H2 H 0.072(7) 1.201(7) 0.693(4) 0.049(14) Uiso 1 1 d .
H3 H 0.200(7) 1.087(7) 0.975(4) 0.053(14) Uiso 1 1 d .
H3A H 0.741(6) 0.701(7) 0.502(3) 0.026(11) Uiso 1 1 d .
H3B H 0.785(6) 0.487(7) 0.507(3) 0.030(11) Uiso 1 1 d .
N1 N 0.6890(4) 0.9315(4) 0.6335(2) 0.0190(7) Uani 1 1 d .
N2 N 0.7149(4) 0.9163(4) 0.8728(2) 0.0207(7) Uani 1 1 d .
N3 N 0.7685(5) 0.5882(5) 0.5442(3) 0.0259(8) Uani 1 1 d .
O1 O 0.2250(4) 0.7808(4) 0.5674(2) 0.0256(7) Uani 1 1 d .
O2 O 0.1590(4) 1.1166(4) 0.6606(2) 0.0216(7) Uani 1 1 d .
O3 O 0.1754(4) 1.1014(3) 0.8949(2) 0.0263(7) Uani 1 1 d .
O4 O 0.8613(4) 0.4148(3) 0.7210(2) 0.0241(7) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0165(18) 0.0197(19) 0.0175(19) -0.0075(15) 0.0022(14) -0.0019(14)
C2 0.0198(18) 0.0145(18) 0.0182(19) -0.0002(15) 0.0004(14) -0.0019(14)
C3 0.0139(17) 0.0181(18) 0.0232(19) -0.0081(15) 0.0030(14) -0.0036(14)
C4 0.034(2) 0.021(2) 0.0139(18) -0.0023(15) -0.0009(15) -0.0041(16)
C5 0.0229(19) 0.0131(18) 0.023(2) 0.0018(15) 0.0005(15) 0.0010(15)
C6 0.027(2) 0.018(2) 0.027(2) -0.0125(16) 0.0033(16) -0.0047(16)
C7 0.0142(18) 0.0164(19) 0.027(2) -0.0038(16) 0.0039(15) -0.0032(14)
C8 0.0202(18) 0.0160(18) 0.0161(19) 0.0018(15) 0.0028(14) -0.0042(15)
C9 0.0243(19) 0.0172(18) 0.0194(19) -0.0053(15) 0.0015(15) -0.0034(15)
C10 0.0194(18) 0.0131(18) 0.023(2) -0.0040(15) 0.0015(15) 0.0000(14)
C11 0.0165(18) 0.0151(18) 0.019(2) -0.0033(15) 0.0040(14) -0.0007(14)
N1 0.0202(16) 0.0142(15) 0.0208(16) -0.0014(13) -0.0021(12) -0.0014(12)
N2 0.0226(16) 0.0193(16) 0.0197(16) -0.0056(13) 0.0034(12) -0.0026(13)
N3 0.039(2) 0.0142(18) 0.0242(19) -0.0064(15) 0.0035(15) -0.0030(15)
O1 0.0430(17) 0.0190(15) 0.0147(14) -0.0072(12) 0.0025(11) -0.0047(13)
O2 0.0301(15) 0.0144(13) 0.0160(13) -0.0010(11) 0.0028(11) 0.0019(11)
O3 0.0479(17) 0.0132(13) 0.0168(14) -0.0092(11) 0.0007(12) -0.0012(11)
O4 0.0305(15) 0.0144(13) 0.0257(14) -0.0032(11) -0.0003(11) -0.0021(11)
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 O1 119.2(3)
C6 C1 C2 121.3(3)
O1 C1 C2 119.4(3)
O2 C2 C1 117.8(3)
O2 C2 C3 122.9(3)
C1 C2 C3 119.3(3)
O3 C3 C4 124.4(3)
O3 C3 C2 116.1(3)
C4 C3 C2 119.5(3)
C5 C4 C3 120.0(3)
C6 C5 C4 120.9(3)
C1 C6 C5 118.9(3)
N1 C7 C8 122.4(3)
N1 C7 C11 118.3(3)
C8 C7 C11 119.3(3)
N2 C8 C7 121.6(3)
N2 C9 C10 122.4(3)
N1 C10 C9 121.9(3)
O4 C11 N3 124.0(3)
O4 C11 C7 119.4(3)
N3 C11 C7 116.5(3)
C10 N1 C7 115.7(3)
C9 N2 C8 116.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.376(5)
C1 O1 1.388(5)
C1 C2 1.388(5)
C2 O2 1.370(4)
C2 C3 1.392(5)
C3 O3 1.359(4)
C3 C4 1.385(5)
C4 C5 1.385(5)
C5 C6 1.377(5)
C7 N1 1.340(4)
C7 C8 1.383(5)
C7 C11 1.500(5)
C8 N2 1.334(5)
C9 N2 1.330(5)
C9 C10 1.385(5)
C10 N1 1.331(4)
C11 O4 1.230(4)
C11 N3 1.323(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652462
2 PubChem 139146116
