#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:27:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178783 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/37/4103774.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_4103774
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            'C17 H13 N3 O5 V'
_chemical_formula_weight         390.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6731(9)
_cell_length_b                   9.8036(9)
_cell_length_c                   16.6299(16)
_cell_measurement_temperature    120(1)
_cell_volume                     1577.0(3)
_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 1.000
_diffrn_measured_fraction_theta_max 0.962
_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  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14616
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  0.9487
_exptl_absorpt_correction_T_min  0.8784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.03 (Sheldrick, 2001)'
_exptl_crystal_colour            blue-green
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'multifaceted block'
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0282P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0672
_reflns_number_gt                3250
_reflns_number_total             3711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja807522n_si_002.cif
_cod_data_source_block           apx744
_cod_database_code               4103774
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 0.84333(4) 0.41233(3) 0.10204(2) 0.01107(9) Uani 1 1 d .
N1 N 0.97786(17) 0.23800(17) 0.10391(10) 0.0119(4) Uani 1 1 d .
N2 N 0.98768(19) 0.50684(17) 0.02193(10) 0.0117(4) Uani 1 1 d .
N3 N 0.71461(19) 0.30184(18) 0.18675(10) 0.0128(4) Uani 1 1 d .
O1 O 0.77711(16) 0.28828(14) 0.01364(8) 0.0139(3) Uani 1 1 d .
O2 O 0.80883(15) 0.10011(15) -0.06160(8) 0.0169(3) Uani 1 1 d .
O3 O 0.98048(15) 0.44707(14) 0.19044(8) 0.0132(3) Uani 1 1 d .
O4 O 1.16140(16) 0.37708(14) 0.26394(8) 0.0180(3) Uani 1 1 d .
O5 O 0.74117(15) 0.54205(14) 0.10247(9) 0.0172(3) Uani 1 1 d .
C1 C 0.9530(2) 0.1363(2) 0.05279(12) 0.0122(5) Uani 1 1 d .
C2 C 1.0288(2) 0.0169(2) 0.05725(12) 0.0157(5) Uani 1 1 d .
H2 H 1.0141 -0.0542 0.0212 0.019 Uiso 1 1 calc R
C3 C 1.1282(2) 0.0069(2) 0.11774(12) 0.0177(5) Uani 1 1 d .
H3 H 1.1793 -0.0730 0.1230 0.021 Uiso 1 1 calc R
C4 C 1.1519(2) 0.1144(2) 0.17014(12) 0.0141(4) Uani 1 1 d .
H4 H 1.2180 0.1077 0.2106 0.017 Uiso 1 1 calc R
C5 C 1.0747(2) 0.2316(2) 0.16053(12) 0.0120(5) Uani 1 1 d .
C6 C 0.8370(2) 0.1730(2) -0.00440(11) 0.0124(4) Uani 1 1 d .
C7 C 1.0770(2) 0.3607(2) 0.21004(12) 0.0135(5) Uani 1 1 d .
C8 C 1.0150(2) 0.4621(2) -0.05310(12) 0.0158(5) Uani 1 1 d .
H8 H 0.9668 0.3871 -0.0726 0.019 Uiso 1 1 calc R
C9 C 1.1119(2) 0.5236(2) -0.10196(13) 0.0181(5) Uani 1 1 d .
H9 H 1.1291 0.4892 -0.1531 0.022 Uiso 1 1 calc R
C10 C 1.1830(2) 0.6360(2) -0.07477(13) 0.0168(5) Uani 1 1 d .
H10 H 1.2484 0.6790 -0.1070 0.020 Uiso 1 1 calc R
C11 C 1.1548(3) 0.6834(2) 0.00165(12) 0.0166(5) Uani 1 1 d .
H11 H 1.2010 0.7592 0.0219 0.020 Uiso 1 1 calc R
C12 C 1.0574(2) 0.6170(2) 0.04752(12) 0.0155(5) Uani 1 1 d .
H12 H 1.0389 0.6501 0.0988 0.019 Uiso 1 1 calc R
C13 C 0.7565(2) 0.2149(2) 0.24446(12) 0.0143(5) Uani 1 1 d .
H13 H 0.8502 0.1943 0.2479 0.017 Uiso 1 1 calc R
C14 C 0.6679(2) 0.1548(2) 0.29869(12) 0.0161(5) Uani 1 1 d .
H14 H 0.7010 0.0942 0.3372 0.019 Uiso 1 1 calc R
C15 C 0.5283(2) 0.1864(2) 0.29482(13) 0.0182(5) Uani 1 1 d .
H15 H 0.4664 0.1493 0.3316 0.022 Uiso 1 1 calc R
C16 C 0.4829(2) 0.2740(2) 0.23541(13) 0.0194(5) Uani 1 1 d .
H16 H 0.3898 0.2962 0.2312 0.023 Uiso 1 1 calc R
C17 C 0.5778(2) 0.3278(2) 0.18249(13) 0.0146(5) Uani 1 1 d .
H17 H 0.5460 0.3848 0.1418 0.017 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
O5 V1 O3 105.55(7)
O5 V1 O1 106.57(7)
O3 V1 O1 147.88(6)
O5 V1 N2 93.51(7)
O3 V1 N2 87.21(6)
O1 V1 N2 90.83(6)
O5 V1 N1 178.78(8)
O3 V1 N1 74.00(6)
O1 V1 N1 73.90(6)
N2 V1 N1 87.60(7)
O5 V1 N3 92.25(7)
O3 V1 N3 89.34(6)
O1 V1 N3 89.42(6)
N2 V1 N3 173.91(7)
N1 V1 N3 86.62(7)
C5 N1 C1 122.94(18)
C5 N1 V1 118.33(14)
C1 N1 V1 118.48(14)
C12 N2 C8 117.13(19)
C12 N2 V1 118.59(14)
C8 N2 V1 124.28(14)
C13 N3 C17 116.89(19)
C13 N3 V1 127.31(15)
C17 N3 V1 115.76(15)
C6 O1 V1 123.36(14)
C7 O3 V1 123.11(13)
N1 C1 C2 120.23(19)
N1 C1 C6 110.89(17)
C2 C1 C6 128.88(19)
C1 C2 C3 117.6(2)
C4 C3 C2 120.9(2)
C5 C4 C3 118.1(2)
N1 C5 C4 120.19(19)
N1 C5 C7 110.92(18)
C4 C5 C7 128.80(19)
O2 C6 O1 125.9(2)
O2 C6 C1 121.05(19)
O1 C6 C1 112.98(17)
O4 C7 O3 125.2(2)
O4 C7 C5 121.33(19)
O3 C7 C5 113.46(18)
N2 C8 C9 122.4(2)
C10 C9 C8 119.8(2)
C9 C10 C11 118.2(2)
C12 C11 C10 119.1(2)
N2 C12 C11 123.28(19)
N3 C13 C14 123.4(2)
C13 C14 C15 118.7(2)
C16 C15 C14 118.8(2)
C17 C16 C15 119.0(2)
N3 C17 C16 123.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
V1 O5 1.6105(15)
V1 O3 2.0094(14)
V1 O1 2.0126(14)
V1 N2 2.1408(18)
V1 N1 2.1484(17)
V1 N3 2.1698(18)
N1 C5 1.330(3)
N1 C1 1.332(3)
N2 C12 1.343(3)
N2 C8 1.349(2)
N3 C13 1.346(3)
N3 C17 1.350(3)
O1 C6 1.305(2)
O2 C6 1.221(2)
O3 C7 1.302(2)
O4 C7 1.223(3)
C1 C2 1.383(3)
C1 C6 1.514(3)
C2 C3 1.395(3)
C3 C4 1.387(3)
C4 C5 1.380(3)
C5 C7 1.510(3)
C8 C9 1.379(3)
C9 C10 1.376(3)
C10 C11 1.380(3)
C11 C12 1.376(3)
C13 C14 1.377(3)
C14 C15 1.387(3)
C15 C16 1.381(3)
C16 C17 1.376(3)
