#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:14:52 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179237 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/57/4315799.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_4315799
loop_
_publ_author_name
'Susan K. Hanson'
'R. Tom Baker'
'John C. Gordon'
'Brian L. Scott'
'David L. Thorn'
_publ_section_title
;
 Aerobic Oxidation of Lignin Models Using a Base Metal Vanadium Catalyst
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5611
_journal_page_last               5618
_journal_paper_doi               10.1021/ic100528n
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C14 H18 N O7 V'
_chemical_formula_weight         363.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.100(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.444(3)
_cell_length_b                   9.690(3)
_cell_length_c                   15.041(4)
_cell_measurement_temperature    120(1)
_cell_volume                     1507.0(8)
_computing_cell_refinement       'SAINT+, v. 7.06 (Bruker AXS, 2001)'
_computing_data_collection       'APEX II, v. 1.08 (Bruker AXS, 2003)'
_computing_data_reduction        'SAINT+, v. 7.06 (Bruker AXS, 2001)'
_computing_molecular_graphics    'SHELXTL, v. 6.10, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.10, (Bruker AXS, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_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  0.0910
_diffrn_reflns_av_sigmaI/netI    0.0851
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13696
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.30
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  0.9595
_exptl_absorpt_correction_T_min  0.9212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.03 (Sheldrick, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                1841
_reflns_number_total             2729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic100528n_si_001_2.cif
_cod_data_source_block           apx767
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4315799
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.37549(5) 1.00454(6) 0.13546(4) 0.01803(18) Uani 1 1 d . . .
O4 O 0.4547(2) 0.9010(2) 0.23973(14) 0.0198(5) Uani 1 1 d . . .
O5 O 0.5377(2) 0.9011(2) 0.38553(15) 0.0229(6) Uani 1 1 d . . .
O2 O 0.2557(2) 1.1477(2) 0.08521(14) 0.0201(5) Uani 1 1 d . . .
N1 N 0.3496(2) 1.1267(3) 0.24337(17) 0.0166(6) Uani 1 1 d . . .
O6 O 0.1770(2) 0.9034(2) 0.16448(13) 0.0189(5) Uani 1 1 d . . .
O7 O 0.3384(2) 0.8714(2) 0.05632(14) 0.0187(5) Uani 1 1 d . . .
O3 O 0.1445(2) 1.3415(2) 0.10469(15) 0.0256(6) Uani 1 1 d . . .
O1 O 0.5039(2) 1.0661(2) 0.10833(14) 0.0236(6) Uani 1 1 d . . .
C2 C 0.2792(3) 1.2412(3) 0.2291(2) 0.0164(7) Uani 1 1 d . . .
C7 C 0.4741(3) 0.9541(3) 0.3212(2) 0.0189(8) Uani 1 1 d . . .
C1 C 0.2209(3) 1.2512(3) 0.1326(2) 0.0203(8) Uani 1 1 d . . .
C5 C 0.3922(3) 1.1698(3) 0.3990(2) 0.0200(8) Uani 1 1 d . . .
H5 H 0.4304 1.1440 0.4563 0.024 Uiso 1 1 calc R . .
C6 C 0.4055(3) 1.0894(3) 0.3257(2) 0.0161(7) Uani 1 1 d . . .
C12 C 0.0246(3) 0.7200(3) 0.1049(2) 0.0251(8) Uani 1 1 d . . .
H12A H -0.0045 0.6936 0.1602 0.038 Uiso 1 1 calc R . .
H12B H 0.0174 0.6427 0.0646 0.038 Uiso 1 1 calc R . .
H12C H -0.0276 0.7946 0.0781 0.038 Uiso 1 1 calc R . .
C11 C 0.2454(3) 0.6646(3) 0.1852(2) 0.0226(8) Uani 1 1 d . . .
H11A H 0.3350 0.6902 0.1907 0.034 Uiso 1 1 calc R . .
H11B H 0.2344 0.5734 0.1605 0.034 Uiso 1 1 calc R . .
H11C H 0.2175 0.6663 0.2434 0.034 Uiso 1 1 calc R . .
C3 C 0.2628(3) 1.3262(3) 0.3001(2) 0.0190(8) Uani 1 1 d . . .
H3 H 0.2137 1.4063 0.2909 0.023 Uiso 1 1 calc R . .
C4 C 0.3206(3) 1.2902(3) 0.3857(2) 0.0217(8) Uani 1 1 d . . .
H4 H 0.3114 1.3470 0.4342 0.026 Uiso 1 1 calc R . .
C9 C 0.1651(3) 0.7660(3) 0.1236(2) 0.0189(8) Uani 1 1 d . . .
C10 C 0.2218(3) 0.7903(3) 0.0348(2) 0.0184(8) Uani 1 1 d . . .
C13 C 0.2596(3) 0.6578(3) -0.0088(2) 0.0246(8) Uani 1 1 d . . .
H13A H 0.2945 0.6795 -0.0628 0.037 Uiso 1 1 calc R . .
H13B H 0.1846 0.6004 -0.0230 0.037 Uiso 1 1 calc R . .
H13C H 0.3234 0.6098 0.0319 0.037 Uiso 1 1 calc R . .
C8 C 0.1108(3) 0.9247(4) 0.2400(2) 0.0298(9) Uani 1 1 d . . .
H8A H 0.0196 0.9124 0.2221 0.045 Uiso 1 1 calc R . .
H8B H 0.1271 1.0167 0.2625 0.045 Uiso 1 1 calc R . .
H8C H 0.1411 0.8593 0.2861 0.045 Uiso 1 1 calc R . .
C14 C 0.1344(3) 0.8763(3) -0.0338(2) 0.0231(8) Uani 1 1 d . . .
H14A H 0.1100 0.9595 -0.0059 0.035 Uiso 1 1 calc R . .
H14B H 0.0583 0.8242 -0.0558 0.035 Uiso 1 1 calc R . .
H14C H 0.1800 0.8993 -0.0830 0.035 Uiso 1 1 calc R . .
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 V1 O7 102.51(11) . . ?
O1 V1 O4 97.09(11) . . ?
O7 V1 O4 101.25(10) . . ?
O1 V1 O2 98.86(11) . . ?
O7 V1 O2 101.04(10) . . ?
O4 V1 O2 148.96(9) . . ?
O1 V1 N1 101.45(11) . . ?
O7 V1 N1 156.04(10) . . ?
O4 V1 N1 75.44(10) . . ?
O2 V1 N1 75.40(10) . . ?
O1 V1 O6 175.29(10) . . ?
O7 V1 O6 73.08(9) . . ?
O4 V1 O6 85.55(8) . . ?
O2 V1 O6 80.59(8) . . ?
N1 V1 O6 82.97(9) . . ?
C7 O4 V1 122.7(2) . . ?
C1 O2 V1 123.1(2) . . ?
C2 N1 C6 122.1(3) . . ?
C2 N1 V1 118.9(2) . . ?
C6 N1 V1 119.0(2) . . ?
C8 O6 C9 116.4(2) . . ?
C8 O6 V1 128.13(19) . . ?
C9 O6 V1 108.68(17) . . ?
C10 O7 V1 130.31(19) . . ?
N1 C2 C3 119.9(3) . . ?
N1 C2 C1 110.5(3) . . ?
C3 C2 C1 129.4(3) . . ?
O5 C7 O4 125.0(3) . . ?
O5 C7 C6 123.2(3) . . ?
O4 C7 C6 111.8(3) . . ?
O3 C1 O2 125.4(3) . . ?
O3 C1 C2 122.6(3) . . ?
O2 C1 C2 111.9(3) . . ?
C6 C5 C4 118.3(3) . . ?
N1 C6 C5 120.6(3) . . ?
N1 C6 C7 110.0(3) . . ?
C5 C6 C7 129.4(3) . . ?
C2 C3 C4 118.9(3) . . ?
C5 C4 C3 120.2(3) . . ?
O6 C9 C11 108.9(2) . . ?
O6 C9 C12 111.5(3) . . ?
C11 C9 C12 111.0(3) . . ?
O6 C9 C10 101.7(2) . . ?
C11 C9 C10 112.2(3) . . ?
C12 C9 C10 111.1(3) . . ?
O7 C10 C13 107.1(3) . . ?
O7 C10 C14 105.0(2) . . ?
C13 C10 C14 109.7(3) . . ?
O7 C10 C9 107.5(2) . . ?
C13 C10 C9 113.3(3) . . ?
C14 C10 C9 113.6(3) . . ?
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
V1 O1 1.573(2) . ?
V1 O7 1.761(2) . ?
V1 O4 1.945(2) . ?
V1 O2 1.948(2) . ?
V1 N1 2.057(3) . ?
V1 O6 2.388(2) . ?
O4 C7 1.318(4) . ?
O5 C7 1.209(4) . ?
O2 C1 1.312(4) . ?
N1 C2 1.332(4) . ?
N1 C6 1.342(4) . ?
O6 C8 1.425(4) . ?
O6 C9 1.465(4) . ?
O7 C10 1.446(4) . ?
O3 C1 1.218(4) . ?
C2 C3 1.379(4) . ?
C2 C1 1.495(4) . ?
C7 C6 1.500(4) . ?
C5 C6 1.374(4) . ?
C5 C4 1.385(4) . ?
C12 C9 1.521(4) . ?
C11 C9 1.519(4) . ?
C3 C4 1.387(4) . ?
C9 C10 1.553(4) . ?
C10 C13 1.519(4) . ?
C10 C14 1.526(4) . ?
