#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/97/2019774.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2019774
loop_
_publ_author_name
'Hejrani-Dalir, Ali'
'Tabatabaee, Masumeh'
'Sheibani, Ali'
_publ_section_title
;
 Synthesis and crystal structure of 2-amino-3-hydroxypyridinium
 dioxido(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)vanadate(V)
 and its conversion to nanostructured V₂O₅
;
_journal_coeditor_code           WQ3079
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229614027983
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '(C5 H7 N2 O) [V (C7 H3 N O4) O2]'
_chemical_formula_moiety         'C7 H3 N O6 V, C5 H7 N2 O'
_chemical_formula_sum            'C12 H10 N3 O7 V'
_chemical_formula_weight         359.17
_chemical_name_systematic
;
2-Amino-3-hydroxypyridinium
dioxido(pyridine-2,6-dicarboxylato-\
κ²O²,N,O⁶)vanadate(V)
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.173(3)
_cell_length_b                   6.3586(7)
_cell_length_c                   8.1089(8)
_cell_measurement_reflns_used    4939
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.63
_cell_volume                     1349.5(3)
_computing_cell_refinement
;
APEX2 (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'Bruker Triumph'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6889
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.462
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0269P)²+1.4082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0832
_reflns_number_gt                1592
_reflns_number_total             1698
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wq3079sup1.cf
_cod_data_source_block           I
_cod_database_code               2019774
_cod_database_fobs_code          2019774
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'x-1/2, y, -z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
V V1 0.391884(15) 0.2500 0.32914(5) 0.01700(14) Uani d S 1 2
O O1 0.46797(6) 0.2500 0.3099(2) 0.0198(4) Uani d S 1 2
O O2 0.54401(7) 0.2500 0.4348(2) 0.0259(4) Uani d S 1 2
O O3 0.32960(6) 0.2500 0.4723(2) 0.0224(4) Uani d S 1 2
O O4 0.29382(7) 0.2500 0.7230(2) 0.0244(4) Uani d S 1 2
O O5 0.37900(5) 0.4580(3) 0.22208(17) 0.0311(3) Uani d . 1 1
N N1 0.41866(7) 0.2500 0.5728(2) 0.0138(4) Uani d S 1 2
C C1 0.49706(9) 0.2500 0.4375(3) 0.0173(5) Uani d S 1 2
C C2 0.46877(9) 0.2500 0.5985(3) 0.0155(5) Uani d S 1 2
C C3 0.48881(10) 0.2500 0.7568(3) 0.0214(5) Uani d S 1 2
H H3A 0.5247 0.2500 0.7750 0.026 Uiso calc SR 1 2
C C4 0.45462(10) 0.2500 0.8874(3) 0.0255(6) Uani d S 1 2
H H4A 0.4671 0.2500 0.9974 0.031 Uiso calc SR 1 2
C C5 0.40203(10) 0.2500 0.8585(3) 0.0234(6) Uani d S 1 2
H H5A 0.3784 0.2500 0.9475 0.028 Uiso calc SR 1 2
C C6 0.38534(9) 0.2500 0.6972(3) 0.0164(5) Uani d S 1 2
C C7 0.33135(9) 0.2500 0.6334(3) 0.0184(5) Uani d S 1 2
O O6 0.10832(7) 0.2500 0.3215(2) 0.0236(4) Uani d S 1 2
N N2 0.24348(8) 0.2500 0.2795(3) 0.0198(5) Uani d S 1 2
N N3 0.19267(9) 0.2500 0.5117(3) 0.0275(6) Uani d S 1 2
C C8 0.19712(9) 0.2500 0.3493(3) 0.0181(5) Uani d S 1 2
C C9 0.15369(9) 0.2500 0.2421(3) 0.0183(5) Uani d S 1 2
C C10 0.16107(9) 0.2500 0.0753(3) 0.0210(5) Uani d S 1 2
H H10A 0.1325 0.2500 0.0032 0.025 Uiso calc SR 1 2
C C11 0.21097(10) 0.2500 0.0097(3) 0.0255(6) Uani d S 1 2
H H11A 0.2161 0.2500 -0.1063 0.031 Uiso calc SR 1 2
C C12 0.25140(10) 0.2500 0.1128(3) 0.0247(6) Uani d S 1 2
H H12A 0.2852 0.2500 0.0699 0.030 Uiso calc SR 1 2
H H6O 0.0869(15) 0.2500 0.261(5) 0.033(10) Uiso d S 1 2
H H2N 0.2678(14) 0.2500 0.342(4) 0.029(9) Uiso d S 1 2
H H3NA 0.2175(15) 0.2500 0.572(5) 0.041(11) Uiso d S 1 2
H H3NB 0.1630(16) 0.2500 0.553(5) 0.044(11) Uiso d S 1 2
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'
V V 0.3005 0.5294 '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_site_symmetry_1
_geom_angle
_geom_angle_publ_flag
O5 V1 O5 7_565 109.70(11) y
O5 V1 O1 7_565 99.56(6) y
O5 V1 O1 . 99.56(6) y
O5 V1 O3 7_565 98.13(6) y
O5 V1 O3 . 98.13(6) y
O1 V1 O3 . 149.01(7) y
O5 V1 N1 7_565 125.13(6) y
O5 V1 N1 . 125.13(6) y
O1 V1 N1 . 74.94(7) y
O3 V1 N1 . 74.07(7) y
C1 O1 V1 . 121.87(15) ?
C7 O3 V1 . 123.45(15) ?
C2 N1 C6 . 121.8(2) ?
C2 N1 V1 . 118.55(16) ?
C6 N1 V1 . 119.63(16) ?
O2 C1 O1 . 125.3(2) ?
O2 C1 C2 . 120.6(2) ?
O1 C1 C2 . 114.1(2) ?
N1 C2 C3 . 121.3(2) ?
N1 C2 C1 . 110.6(2) ?
C3 C2 C1 . 128.2(2) ?
C2 C3 C4 . 117.6(2) ?
C2 C3 H3A . 121.2 ?
C4 C3 H3A . 121.2 ?
C3 C4 C5 . 120.5(2) ?
C3 C4 H4A . 119.7 ?
C5 C4 H4A . 119.7 ?
C6 C5 C4 . 118.1(2) ?
C6 C5 H5A . 120.9 ?
C4 C5 H5A . 120.9 ?
N1 C6 C5 . 120.7(2) ?
N1 C6 C7 . 110.7(2) ?
C5 C6 C7 . 128.6(2) ?
O4 C7 O3 . 124.5(2) ?
O4 C7 C6 . 123.4(2) ?
O3 C7 C6 . 112.1(2) ?
C9 O6 H6O . 111(3) ?
C8 N2 C12 . 123.7(2) ?
C8 N2 H2N . 116(2) ?
C12 N2 H2N . 120(2) ?
C8 N3 H3NA . 122(3) ?
C8 N3 H3NB . 119(3) ?
H3NA N3 H3NB . 120(4) ?
N3 C8 N2 . 120.1(2) ?
N3 C8 C9 . 122.3(2) ?
N2 C8 C9 . 117.6(2) ?
O6 C9 C10 . 126.6(2) ?
O6 C9 C8 . 114.1(2) ?
C10 C9 C8 . 119.3(2) ?
C9 C10 C11 . 120.3(2) ?
C9 C10 H10A . 119.9 ?
C11 C10 H10A . 119.9 ?
C12 C11 C10 . 119.6(2) ?
C12 C11 H11A . 120.2 ?
C10 C11 H11A . 120.2 ?
C11 C12 N2 . 119.6(2) ?
C11 C12 H12A . 120.2 ?
N2 C12 H12A . 120.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 O5 7_565 1.6176(15) y
V1 O5 . 1.6176(15) y
V1 O1 . 1.9976(18) y
V1 O3 . 2.0012(18) y
V1 N1 . 2.096(2) y
O1 C1 . 1.285(3) ?
O2 C1 . 1.229(3) ?
O3 C7 . 1.307(3) ?
O4 C7 . 1.222(3) ?
N1 C2 . 1.328(3) ?
N1 C6 . 1.334(3) ?
C1 C2 . 1.500(3) ?
C2 C3 . 1.387(3) ?
C3 C4 . 1.387(4) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.396(4) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.379(3) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.505(3) ?
O6 C9 . 1.351(3) ?
O6 H6O . 0.74(4) ?
N2 C8 . 1.339(3) ?
N2 C12 . 1.367(4) ?
N2 H2N . 0.81(4) ?
N3 C8 . 1.322(4) ?
N3 H3NA . 0.81(4) ?
N3 H3NB . 0.85(4) ?
C8 C9 . 1.431(3) ?
C9 C10 . 1.367(4) ?
C10 C11 . 1.410(3) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.348(4) ?
C11 H11A . 0.9500 ?
C12 H12A . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O6 H6O O2 2_455 0.74(4) 1.95(4) 2.675(3) 166(4)
N2 H2N O3 . 0.81(4) 1.93(4) 2.743(3) 175(3)
N3 H3NA O4 . 0.81(4) 2.34(4) 3.153(3) 175(4)
N3 H3NB O5 4_565 0.85(4) 2.56(3) 3.143(2) 128(2)
N3 H3NB O5 6_656 0.85(4) 2.56(3) 3.143(2) 128(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion
O5 V1 O1 C1 7_565 -123.99(6)
O5 V1 O1 C1 . 123.99(6)
O3 V1 O1 C1 . 0.0
N1 V1 O1 C1 . 0.0
O5 V1 O3 C7 7_565 124.32(6)
O5 V1 O3 C7 . -124.31(6)
O1 V1 O3 C7 . 0.0
N1 V1 O3 C7 . 0.0
O5 V1 N1 C2 7_565 91.20(7)
O5 V1 N1 C2 . -91.20(7)
O1 V1 N1 C2 . 0.0
O3 V1 N1 C2 . 180.0
O5 V1 N1 C6 7_565 -88.80(7)
O5 V1 N1 C6 . 88.80(7)
O1 V1 N1 C6 . 180.0
O3 V1 N1 C6 . 0.0
V1 O1 C1 O2 . 180.0
V1 O1 C1 C2 . 0.0
C6 N1 C2 C3 . 0.0
V1 N1 C2 C3 . 180.0
C6 N1 C2 C1 . 180.0
V1 N1 C2 C1 . 0.0
O2 C1 C2 N1 . 180.0
O1 C1 C2 N1 . 0.0
O2 C1 C2 C3 . 0.0
O1 C1 C2 C3 . 180.0
N1 C2 C3 C4 . 0.0
C1 C2 C3 C4 . 180.0
C2 C3 C4 C5 . 0.0
C3 C4 C5 C6 . 0.0
C2 N1 C6 C5 . 0.0
V1 N1 C6 C5 . 180.0
C2 N1 C6 C7 . 180.0
V1 N1 C6 C7 . 0.0
C4 C5 C6 N1 . 0.0
C4 C5 C6 C7 . 180.0
V1 O3 C7 O4 . 180.0
V1 O3 C7 C6 . 0.0
N1 C6 C7 O4 . 180.0
C5 C6 C7 O4 . 0.0
N1 C6 C7 O3 . 0.0
C5 C6 C7 O3 . 180.0
C12 N2 C8 N3 . 180.0
C12 N2 C8 C9 . 0.0
N3 C8 C9 O6 . 0.0
N2 C8 C9 O6 . 180.0
N3 C8 C9 C10 . 180.0
N2 C8 C9 C10 . 0.0
O6 C9 C10 C11 . 180.0
C8 C9 C10 C11 . 0.0
C9 C10 C11 C12 . 0.0
C10 C11 C12 N2 . 0.0
C8 N2 C12 C11 . 0.0
