#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:27:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178783 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/37/4103773.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_4103773
loop_
_publ_author_name
'Susan K. Hanson'
'R. Tom Baker'
'John C. Gordon'
'Brian L. Scott'
'Andrew D. Sutton'
'David L. Thorn'
_publ_section_title
;
 Aerobic Oxidation of Pinacol by Vanadium(V) Dipicolinate Complexes:
 Evidence for Reduction to Vanadium(III)
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              428
_journal_page_last               429
_journal_paper_doi               10.1021/ja807522n
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C13 H15 N O6 V'
_chemical_formula_weight         332.20
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.204(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2898(13)
_cell_length_b                   16.096(3)
_cell_length_c                   14.357(3)
_cell_measurement_temperature    141(2)
_cell_volume                     1453.5(5)
_computing_cell_refinement       'SAINT 4.05 (Bruker, 1996)'
_computing_data_collection       'SMART 4.210 (Bruker, 1996)'
_computing_data_reduction        'SAINT 4.05 (Bruker, 1996)'
_computing_molecular_graphics    'SHELXTL 6.10 (Bruker, 2001)'
_computing_publication_material  'SHELXTL 6.10 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      141(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 1k CCD'
_diffrn_measurement_method       'φ 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  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13723
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  0.9455
_exptl_absorpt_correction_T_min  0.8598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.03 (Sheldrick, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.528
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.528
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0427
_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)+(0.0381P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                2148
_reflns_number_total             2577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja807522n_si_001.cif
_cod_data_source_block           xpl066
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4103773
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
V1 V 0.24011(8) 0.66474(3) 0.23257(3) 0.01217(16) Uani 1 1 d .
O1 O 0.5062(3) 0.62468(11) 0.17807(13) 0.0145(4) Uani 1 1 d .
O2 O 0.7301(3) 0.61916(12) 0.05728(13) 0.0157(5) Uani 1 1 d .
O3 O -0.0339(3) 0.72079(11) 0.22036(13) 0.0141(4) Uani 1 1 d .
O4 O -0.2453(3) 0.80816(12) 0.14008(13) 0.0173(5) Uani 1 1 d .
O5 O 0.0902(3) 0.56342(11) 0.14635(13) 0.0133(4) Uani 1 1 d .
O6 O 0.1861(3) 0.58581(12) 0.31575(13) 0.0165(5) Uani 1 1 d .
O7 O 0.3455(3) 0.73434(12) 0.29603(13) 0.0182(5) Uani 1 1 d .
N1 N 0.2462(3) 0.71624(14) 0.10102(15) 0.0107(5) Uani 1 1 d .
C1 C 0.5672(5) 0.64327(17) 0.0938(2) 0.0145(6) Uani 1 1 d .
C2 C 0.4094(4) 0.69893(17) 0.04508(19) 0.0118(6) Uani 1 1 d .
C3 C 0.4141(4) 0.72879(18) -0.04515(19) 0.0144(6) Uani 1 1 d .
H3 H 0.5287 0.7177 -0.0840 0.017 Uiso 1 1 calc R
C4 C 0.2423(4) 0.77591(17) -0.07626(19) 0.0143(6) Uani 1 1 d .
H4 H 0.2408 0.7961 -0.1370 0.017 Uiso 1 1 calc R
C5 C 0.0724(4) 0.79310(16) -0.01692(19) 0.0142(6) Uani 1 1 d .
H5 H -0.0425 0.8249 -0.0370 0.017 Uiso 1 1 calc R
C6 C 0.0802(4) 0.76140(17) 0.07263(19) 0.0120(6) Uani 1 1 d .
C7 C -0.0852(4) 0.76700(17) 0.14797(19) 0.0133(6) Uani 1 1 d .
C8 C 0.0985(5) 0.48385(17) 0.1964(2) 0.0153(6) Uani 1 1 d .
C9 C 0.0711(5) 0.50781(18) 0.3013(2) 0.0178(7) Uani 1 1 d .
C10 C 0.3149(5) 0.44579(18) 0.1772(2) 0.0177(7) Uani 1 1 d .
H10A H 0.4242 0.4817 0.2010 0.027 Uiso 1 1 calc R
H10B H 0.3328 0.4390 0.1113 0.027 Uiso 1 1 calc R
H10C H 0.3245 0.3926 0.2072 0.027 Uiso 1 1 calc R
C11 C -0.0758(5) 0.42741(18) 0.1588(2) 0.0197(7) Uani 1 1 d .
H11A H -0.2121 0.4517 0.1713 0.030 Uiso 1 1 calc R
H11B H -0.0666 0.3741 0.1886 0.030 Uiso 1 1 calc R
H11C H -0.0586 0.4207 0.0928 0.030 Uiso 1 1 calc R
C12 C -0.1601(5) 0.52510(19) 0.3278(2) 0.0207(7) Uani 1 1 d .
H12A H -0.2195 0.5652 0.2857 0.031 Uiso 1 1 calc R
H12B H -0.1653 0.5464 0.3902 0.031 Uiso 1 1 calc R
H12C H -0.2405 0.4745 0.3243 0.031 Uiso 1 1 calc R
C13 C 0.1672(5) 0.44435(19) 0.3679(2) 0.0227(7) Uani 1 1 d .
H13A H 0.3123 0.4339 0.3509 0.034 Uiso 1 1 calc R
H13B H 0.0877 0.3935 0.3644 0.034 Uiso 1 1 calc R
H13C H 0.1622 0.4656 0.4303 0.034 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
O7 V1 O6 101.48(10)
O7 V1 O3 95.28(9)
O6 V1 O3 102.70(9)
O7 V1 O1 96.07(9)
O6 V1 O1 101.46(9)
O3 V1 O1 150.60(8)
O7 V1 N1 103.46(9)
O6 V1 N1 155.05(9)
O3 V1 N1 75.61(8)
O1 V1 N1 75.40(8)
O7 V1 O5 178.25(9)
O6 V1 O5 76.77(8)
O3 V1 O5 85.27(8)
O1 V1 O5 84.20(7)
N1 V1 O5 78.29(8)
C1 O1 V1 123.28(18)
C7 O3 V1 123.04(17)
C8 O5 V1 110.39(15)
C9 O6 V1 127.84(17)
C6 N1 C2 122.2(2)
C6 N1 V1 118.77(18)
C2 N1 V1 118.93(18)
O2 C1 O1 125.3(3)
O2 C1 C2 122.9(3)
O1 C1 C2 111.8(2)
N1 C2 C3 120.7(3)
N1 C2 C1 110.5(2)
C3 C2 C1 128.7(3)
C2 C3 C4 118.1(3)
C3 C4 C5 120.5(3)
C6 C5 C4 118.0(3)
N1 C6 C5 120.6(2)
N1 C6 C7 110.8(2)
C5 C6 C7 128.5(3)
O4 C7 O3 125.7(3)
O4 C7 C6 122.8(3)
O3 C7 C6 111.4(2)
O5 C8 C10 107.0(2)
O5 C8 C11 108.8(2)
C10 C8 C11 109.9(2)
O5 C8 C9 104.6(2)
C10 C8 C9 112.1(2)
C11 C8 C9 114.0(2)
O6 C9 C13 107.0(2)
O6 C9 C12 106.2(2)
C13 C9 C12 109.9(2)
O6 C9 C8 107.0(2)
C13 C9 C8 113.2(2)
C12 C9 C8 113.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
V1 O7 1.5876(19)
V1 O6 1.7772(19)
V1 O3 1.9528(19)
V1 O1 1.9594(19)
V1 N1 2.063(2)
V1 O5 2.2522(19)
O1 C1 1.305(3)
O2 C1 1.216(3)
O3 C7 1.317(3)
O4 C7 1.210(3)
O5 C8 1.469(3)
O6 C9 1.463(3)
N1 C6 1.335(3)
N1 C2 1.335(3)
C1 C2 1.507(4)
C2 C3 1.382(4)
C3 C4 1.392(4)
C4 C5 1.397(4)
C5 C6 1.384(4)
C6 C7 1.506(4)
C8 C10 1.519(4)
C8 C11 1.521(4)
C8 C9 1.565(4)
C9 C13 1.523(4)
C9 C12 1.530(4)
