#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:48:41 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179264 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/84/4318403.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_4318403
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            'C26 H34 N O6 V'
_chemical_formula_weight         507.48
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           146
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   23.754(5)
_cell_length_b                   23.754(5)
_cell_length_c                   12.836(3)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      7
_cell_volume                     6272(2)
_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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5778
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   semi-empirical
_exptl_crystal_colour            dark
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       parallelopiped
_exptl_crystal_F_000             2412
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.089
_refine_ls_goodness_of_fit_obs   1.097
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4903
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.091
_refine_ls_restrained_S_obs      1.097
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_obs          0.0515
_refine_ls_shift/esd_max         -0.032
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0944P)²+1.2196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1461
_refine_ls_wR_factor_obs         0.1344
_reflns_number_observed          4133
_reflns_number_total             4910
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic020259d_2.cif
_cod_data_source_block           728vo
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
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^)+(0.0944P)^2^+1.2196P] 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^)+(0.0944P)^2^+1.2196P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        6272.4(24)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               4318403
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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 0.26140(3) -0.58846(3) -0.40989(5) 0.0427(2) Uani 1 d . .
N N 0.3529(2) -0.5589(2) -0.4733(2) 0.0393(7) Uani 1 d . .
O1 O 0.2739(2) -0.5603(2) -0.2945(3) 0.0650(9) Uani 1 d . .
O2 O 0.27778(14) -0.66055(15) -0.3782(3) 0.0551(8) Uani 1 d . .
O3 O 0.26701(14) -0.51766(15) -0.4819(2) 0.0536(7) Uani 1 d . .
O4 O 0.23392(12) -0.64181(13) -0.5719(2) 0.0461(7) Uani 1 d . .
O5 O 0.17243(13) -0.64210(14) -0.4082(2) 0.0459(7) Uani 1 d . .
O6 O 0.3453(2) -0.6992(2) -0.3748(3) 0.0783(11) Uani 1 d . .
C1 C 0.3344(2) -0.6548(2) -0.3905(4) 0.0522(10) Uani 1 d . .
C2 C 0.3871(2) -0.5888(2) -0.4255(3) 0.0460(9) Uani 1 d . .
C3 C 0.3733(2) -0.5287(2) -0.5605(3) 0.0381(8) Uani 1 d . .
C4 C 0.3412(2) -0.5005(2) -0.6196(3) 0.0434(9) Uani 1 d . .
C5 C 0.3625(2) -0.4783(2) -0.7211(4) 0.0518(10) Uani 1 d . .
H5A H 0.3957(2) -0.4829(2) -0.7507(4) 0.062 Uiso 1 calc R .
C6 C 0.3337(3) -0.4495(3) -0.7769(4) 0.0664(14) Uani 1 d . .
C7 C 0.2875(3) -0.4403(3) -0.7323(5) 0.075(2) Uani 1 d . .
C8 C 0.2664(2) -0.4604(3) -0.6325(5) 0.0660(13) Uani 1 d . .
C9 C 0.2908(2) -0.4944(2) -0.5751(3) 0.0467(10) Uani 1 d . .
C10 C 0.1693(2) -0.6874(2) -0.5710(3) 0.0384(8) Uani 1 d . .
C11 C 0.1392(2) -0.7328(2) -0.6479(3) 0.0428(8) Uani 1 d . .
C12 C 0.0720(2) -0.7763(2) -0.6424(3) 0.0450(9) Uani 1 d . .
C13 C 0.0394(2) -0.7703(2) -0.5563(3) 0.0477(10) Uani 1 d . .
C14 C 0.0687(2) -0.7258(2) -0.4752(3) 0.0402(9) Uani 1 d . .
C16 C 0.4305(2) -0.5490(3) -0.3314(4) 0.0688(14) Uani 1 d . .
C17 C 0.4611(4) -0.5820(4) -0.2784(6) 0.109(3) Uani 1 d . .
H17A H 0.4281(4) -0.6244(4) -0.2561(6) 0.164 Uiso 1 calc R .
H17B H 0.4850(4) -0.5569(4) -0.2189(6) 0.164 Uiso 1 calc R .
H17C H 0.4902(4) -0.5861(4) -0.3256(6) 0.164 Uiso 1 calc R .
C18 C 0.4816(3) -0.4807(3) -0.3686(5) 0.093(2) Uani 1 d . .
C19 C 0.0353(2) -0.8270(2) -0.7270(4) 0.0549(11) Uani 1 d . .
C20 C -0.0108(4) -0.8927(3) -0.6795(5) 0.104(2) Uani 1 d . .
H20A H 0.0133(4) -0.9067(3) -0.6373(5) 0.156 Uiso 1 calc R .
H20B H -0.0327(4) -0.9238(3) -0.7340(5) 0.156 Uiso 1 calc R .
H20C H -0.0422(4) -0.8893(3) -0.6370(5) 0.156 Uiso 1 calc R .
C21 C 0.0815(3) -0.8381(4) -0.7957(7) 0.116(3) Uani 1 d . .
C22 C -0.0023(5) -0.8047(4) -0.7933(6) 0.115(3) Uani 1 d . .
H22A H 0.0271(5) -0.7631(4) -0.8232(6) 0.173 Uiso 1 calc R .
H22B H -0.0337(5) -0.8012(4) -0.7510(6) 0.173 Uiso 1 calc R .
H22C H -0.0242(5) -0.8357(4) -0.8480(6) 0.173 Uiso 1 calc R .
C23 C 0.0302(2) -0.7229(2) -0.3822(3) 0.0475(10) Uani 1 d . .
C24 C 0.0535(3) -0.7411(3) -0.2836(4) 0.0650(13) Uani 1 d . .
C25 C 0.0404(3) -0.6537(3) -0.3693(4) 0.0645(13) Uani 1 d . .
C26 C -0.0432(2) -0.7695(3) -0.3938(4) 0.0661(13) Uani 1 d . .
H26C H -0.0441(2) -0.8102(3) -0.3875(4) 0.079 Uiso 1 d R .
C15 C 0.1366(2) -0.6847(2) -0.4834(3) 0.0375(8) Uani 1 d . .
H2 H 0.4159 -0.5935 -0.4762 0.080 Uiso 1 d . .
H3 H 0.4065 -0.5286 -0.5981 0.080 Uiso 1 d . .
H4 H 0.2564 -0.6570 -0.6195 0.080 Uiso 1 d . .
H6 H 0.3508 -0.4398 -0.8431 0.080 Uiso 1 d . .
H7 H 0.2792 -0.4189 -0.7824 0.080 Uiso 1 d . .
H8 H 0.2353 -0.4581 -0.5880 0.080 Uiso 1 d . .
H11 H 0.1691 -0.7318 -0.7043 0.080 Uiso 1 d . .
H13 H -0.0039 -0.7980 -0.5484 0.080 Uiso 1 d . .
H24C H 0.0239 -0.7528 -0.2236 0.080 Uiso 1 d . .
H25C H 0.0898 -0.6144 -0.3622 0.080 Uiso 1 d . .
H24B H 0.0960 -0.7031 -0.2592 0.080 Uiso 1 d . .
H24A H 0.0598 -0.7768 -0.2758 0.080 Uiso 1 d . .
H25B H 0.0358 -0.6233 -0.4213 0.080 Uiso 1 d . .
H26B H -0.0744 -0.7752 -0.3357 0.080 Uiso 1 d . .
H18C H 0.4858 -0.4961 -0.4186 0.080 Uiso 1 d . .
H26A H -0.0429 -0.7669 -0.4571 0.080 Uiso 1 d . .
H18B H 0.5013 -0.4633 -0.3142 0.080 Uiso 1 d . .
H16A H 0.4032 -0.5474 -0.2751 0.080 Uiso 1 d . .
H18A H 0.4557 -0.4635 -0.3787 0.080 Uiso 1 d . .
H21A H 0.1236 -0.8371 -0.7749 0.080 Uiso 1 d . .
H21C H 0.0546 -0.8759 -0.8521 0.080 Uiso 1 d . .
H21B H 0.1206 -0.7999 -0.8324 0.080 Uiso 1 d . .
H25C H 0.0144 -0.6529 -0.3165 0.080 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 100.88(15) . . y
O1 V O3 99.7(2) . . y
O5 V O3 99.76(13) . . y
O1 V O2 95.5(2) . . y
O5 V O2 93.04(12) . . y
O3 V O2 157.85(13) . . y
O1 V N 106.10(15) . . y
O5 V N 151.46(13) . . y
O3 V N 84.88(13) . . y
O2 V N 75.43(13) . . y
O1 V O4 173.31(14) . . y
O5 V O4 74.00(11) . . y
O3 V O4 85.58(12) . . y
O2 V O4 80.63(12) . . y
N V O4 78.35(11) . . y
C3 N C2 119.5(3) . . ?
C3 N V 124.4(3) . . ?
C2 N V 114.4(2) . . ?
C1 O2 V 121.9(3) . . ?
C9 O3 V 130.5(3) . . ?
C10 O4 V 108.6(2) . . ?
C15 O5 V 125.9(2) . . ?
O6 C1 O2 123.1(4) . . ?
O6 C1 C2 121.6(4) . . ?
O2 C1 C2 115.3(4) . . ?
N C2 C1 104.9(3) . . ?
N C2 C16 113.0(4) . . ?
C1 C2 C16 110.7(4) . . ?
N C3 C4 124.9(3) . . ?
C9 C4 C5 120.5(4) . . ?
C9 C4 C3 120.6(4) . . ?
C5 C4 C3 118.9(4) . . ?
C6 C5 C4 119.5(4) . . ?
C7 C6 C5 120.2(5) . . ?
C6 C7 C8 121.7(5) . . ?
C7 C8 C9 120.3(5) . . ?
O3 C9 C4 122.4(4) . . ?
O3 C9 C8 120.0(4) . . ?
C4 C9 C8 117.5(4) . . ?
O4 C10 C11 123.8(3) . . ?
O4 C10 C15 113.8(3) . . ?
C11 C10 C15 122.4(3) . . ?
C10 C11 C12 119.8(4) . . ?
C13 C12 C11 116.6(4) . . ?
C13 C12 C19 121.0(4) . . ?
C11 C12 C19 122.3(4) . . ?
C12 C13 C14 125.2(4) . . ?
C13 C14 C15 115.6(3) . . ?
C13 C14 C23 122.3(3) . . ?
C15 C14 C23 122.0(4) . . ?
C17 C16 C18 111.4(5) . . ?
C17 C16 C2 112.7(5) . . ?
C18 C16 C2 109.4(4) . . ?
C22 C19 C20 109.8(6) . . ?
C22 C19 C12 109.2(4) . . ?
C20 C19 C12 111.0(4) . . ?
C22 C19 C21 109.6(6) . . ?
C20 C19 C21 105.4(5) . . ?
C12 C19 C21 111.7(4) . . ?
C14 C23 C24 108.9(3) . . ?
C14 C23 C26 112.5(4) . . ?
C24 C23 C26 108.5(4) . . ?
C14 C23 C25 110.7(3) . . ?
C24 C23 C25 109.0(4) . . ?
C26 C23 C25 107.1(4) . . ?
O5 C15 C10 117.2(3) . . ?
O5 C15 C14 122.7(3) . . ?
C10 C15 C14 120.1(4) . . ?
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 1.592(3) . y
V O5 1.843(3) . y
V O3 1.865(3) . y
V O2 1.979(3) . y
V N 2.087(3) . y
V O4 2.352(3) . y
N C3 1.286(5) . ?
N C2 1.455(5) . ?
O2 C1 1.292(5) . ?
O3 C9 1.320(5) . ?
O4 C10 1.366(4) . y
O5 C15 1.349(5) . y
O6 C1 1.222(5) . ?
C1 C2 1.504(6) . ?
C2 C16 1.562(7) . ?
C3 C4 1.456(5) . ?
C4 C9 1.398(6) . ?
C4 C5 1.401(6) . ?
C5 C6 1.385(7) . ?
C6 C7 1.348(9) . ?
C7 C8 1.370(8) . ?
C8 C9 1.412(7) . ?
C10 C11 1.370(6) . y
C10 C15 1.387(5) . y
C11 C12 1.404(5) . y
C12 C13 1.396(6) . y
C12 C19 1.529(6) . ?
C13 C14 1.396(6) . y
C14 C15 1.411(5) . y
C14 C23 1.526(5) . ?
C16 C17 1.475(9) . ?
C16 C18 1.538(9) . ?
C19 C22 1.509(8) . ?
C19 C20 1.516(8) . ?
C19 C21 1.530(8) . ?
C23 C24 1.529(6) . ?
C23 C26 1.535(6) . ?
C23 C25 1.547(6) . ?
