#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:48:41 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179264 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/84/4318402.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_4318402
loop_
_publ_author_name
'Bharat Baruah'
'Samir Das'
'Animesh Chakravorty'
_publ_section_title
;
 A Family of Vanadate Esters of Monoionized and Diionized Aromatic
 1,2-Diols: Synthesis, Structure, and Redox Activity
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4502
_journal_page_last               4508
_journal_paper_doi               10.1021/ic020259d
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C15 H12 N O6 V'
_chemical_formula_weight         353.20
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 101.70(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.436(4)
_cell_length_b                   9.757(2)
_cell_length_c                   14.410(5)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      7
_cell_volume                     1436.8(8)
_computing_cell_refinement       'Siemens P3/P4-PC V4.27'
_computing_data_collection       'Siemens P3/P4-PC V4.27'
_computing_data_reduction        'Siemens P3/P4-PC V4.27'
_computing_molecular_graphics    'Siemens SHELXTL V5.03 PC'
_computing_publication_material  'Siemens SHELXTL V5.03 PC'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens R3m/V'
_diffrn_measurement_method       'ω 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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2680
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   semi-empirical
_exptl_crystal_colour            dark
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_description       parallelopiped
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.081
_refine_ls_goodness_of_fit_obs   1.069
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_restrained_S_obs      1.069
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_obs          0.0577
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0783P)²+2.7340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1708
_refine_ls_wR_factor_obs         0.1447
_reflns_number_observed          1898
_reflns_number_total             2498
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic020259d_1.cif
_cod_data_source_block           712vo
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_geom_bond_publ_flag'
value 'Y' changed to 'y' according to the built-in table from CIF
Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (8
times).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+2.7340P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+2.7340P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4318402
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
V V 0.70808(8) 0.17100(8) 0.56171(6) 0.0420(3) Uani 1 d . .
O1 O 0.6116(4) 0.0953(4) 0.4793(2) 0.0592(10) Uani 1 d . .
O2 O 0.6737(3) 0.0630(3) 0.6692(2) 0.0456(8) Uani 1 d . .
O3 O 0.7428(4) 0.3267(3) 0.4972(2) 0.0522(9) Uani 1 d . .
O4 O 0.8684(3) 0.2755(3) 0.6842(2) 0.0447(8) Uani 1 d . .
O5 O 0.8564(3) 0.0697(3) 0.5657(2) 0.0467(8) Uani 1 d . .
O6 O 0.5397(3) 0.0179(3) 0.7670(3) 0.0531(9) Uani 1 d . .
N N 0.5849(4) 0.2957(4) 0.6194(3) 0.0444(9) Uani 1 d . .
C1 C 0.5769(4) 0.0895(4) 0.7076(3) 0.0422(11) Uani 1 d . .
C2 C 0.5038(5) 0.2196(6) 0.6731(4) 0.0554(13) Uani 1 d . .
C3 C 0.5847(5) 0.4285(5) 0.6216(3) 0.0462(11) Uani 1 d . .
H3A H 0.5265(5) 0.4722(5) 0.6562(3) 0.055 Uiso 1 d R .
C4 C 0.6635(5) 0.5148(5) 0.5758(3) 0.0455(11) Uani 1 d . .
C5 C 0.6657(6) 0.6577(5) 0.5912(4) 0.0548(13) Uani 1 d . .
C6 C 0.7432(7) 0.7426(6) 0.5500(4) 0.069(2) Uani 1 d . .
C7 C 0.8196(6) 0.6866(6) 0.4920(4) 0.065(2) Uani 1 d . .
H7A H 0.8733(6) 0.7454(6) 0.4624(4) 0.078 Uiso 1 d R .
C8 C 0.8207(5) 0.5487(5) 0.4751(4) 0.0544(13) Uani 1 d . .
C9 C 0.7433(5) 0.4609(4) 0.5165(3) 0.0437(11) Uani 1 d . .
C10 C 0.9775(4) 0.1950(4) 0.6944(3) 0.0402(10) Uani 1 d . .
C11 C 1.0898(5) 0.2164(5) 0.7610(4) 0.0513(12) Uani 1 d . .
C12 C 1.1950(5) 0.1287(6) 0.7637(4) 0.0610(14) Uani 1 d . .
C13 C 1.1854(6) 0.0192(7) 0.7025(5) 0.069(2) Uani 1 d . .
H13A H 1.2586(6) -0.0415(7) 0.7058(5) 0.082 Uiso 1 d R .
C14 C 1.0718(5) -0.0053(6) 0.6372(4) 0.0580(14) Uani 1 d . .
H14A H 1.0651(5) -0.0831(6) 0.5957(4) 0.070 Uiso 1 d R .
C15 C 0.9672(4) 0.0843(5) 0.6314(3) 0.0413(10) Uani 1 d . .
H8A H 0.8717 0.5109 0.4367 0.081 Uiso 1 d . .
H2A H 0.4265 0.1920 0.6374 0.056 Uiso 1 d . .
H11A H 1.1008 0.2842 0.8055 0.052 Uiso 1 d . .
H12A H 1.2746 0.1399 0.8053 0.073 Uiso 1 d . .
H2B H 0.5018 0.2700 0.7325 0.068 Uiso 1 d . .
H5A H 0.6063 0.6874 0.6296 0.074 Uiso 1 d . .
H6A H 0.7505 0.8349 0.5643 0.113 Uiso 1 d . .
H4 H 0.9020 0.3744 0.7056 0.050 Uiso 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V O5 100.3(2) . . y
O1 V O3 99.5(2) . . y
O5 V O3 102.0(2) . . y
O1 V O2 98.7(2) . . y
O5 V O2 88.50(14) . . y
O3 V O2 156.86(14) . . y
O1 V N 103.0(2) . . y
O5 V N 154.0(2) . . y
O3 V N 85.41(15) . . y
O2 V N 76.73(14) . . y
O1 V O4 175.5(2) . . y
O5 V O4 75.32(13) . . y
O3 V O4 80.95(14) . . y
O2 V O4 81.93(13) . . y
N V O4 81.46(13) . . y
C1 O2 V 121.4(3) . . ?
C9 O3 V 133.6(3) . . ?
C10 O4 V 106.1(3) . . ?
C15 O5 V 124.6(3) . . ?
C3 N C2 119.4(4) . . ?
C3 N V 127.1(3) . . ?
C2 N V 112.9(3) . . ?
O6 C1 O2 125.4(4) . . ?
O6 C1 C2 119.8(4) . . ?
O2 C1 C2 114.8(4) . . ?
N C2 C1 107.0(4) . . ?
N C3 C4 125.0(5) . . ?
C9 C4 C5 118.1(5) . . ?
C9 C4 C3 121.8(4) . . ?
C5 C4 C3 120.2(5) . . ?
C6 C5 C4 121.4(5) . . ?
C5 C6 C7 119.1(5) . . ?
C8 C7 C6 121.6(5) . . ?
C7 C8 C9 120.2(5) . . ?
O3 C9 C8 119.4(5) . . ?
O3 C9 C4 120.9(4) . . ?
C8 C9 C4 119.7(4) . . ?
O4 C10 C11 124.3(4) . . ?
O4 C10 C15 114.8(4) . . ?
C11 C10 C15 120.9(4) . . ?
C10 C11 C12 119.0(5) . . ?
C13 C12 C11 120.5(5) . . ?
C12 C13 C14 120.9(5) . . ?
C13 C14 C15 119.3(5) . . ?
O5 C15 C14 122.0(4) . . ?
O5 C15 C10 118.6(4) . . ?
C14 C15 C10 119.4(5) . . ?
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
V O1 1.576(3) . y
V O5 1.827(3) . y
V O3 1.855(3) . y
V O2 1.966(3) . y
V N 2.063(4) . y
V O4 2.399(3) . y
O2 C1 1.273(6) . ?
O3 C9 1.338(5) . ?
O4 C10 1.366(5) . y
O5 C15 1.345(5) . y
O6 C1 1.227(5) . ?
N C3 1.297(6) . ?
N C2 1.460(6) . ?
C1 C2 1.513(7) . ?
C3 C4 1.428(6) . ?
C4 C9 1.410(7) . ?
C4 C5 1.412(6) . ?
C5 C6 1.373(8) . ?
C6 C7 1.380(8) . ?
C7 C8 1.368(8) . ?
C8 C9 1.392(7) . ?
C10 C11 1.372(7) . y
C10 C15 1.402(6) . y
C11 C12 1.386(7) . y
C12 C13 1.376(8) . y
C13 C14 1.377(8) . y
C14 C15 1.387(7) . y
