#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:26:03 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179721 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/23/7002330.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_7002330
loop_
_publ_author_name
'Nilsson, Jessica'
'Degerman, Eva'
'Haukka, Matti'
'Lisensky, George C.'
'Garribba, Eugenio'
'Yoshikawa, Yutaka'
'Sakurai, Hiromu'
'Enyedy, Eva A.'
'Kiss, Tamás'
'Esbak, Hossein'
'Rehder, Dieter'
'Nordlander, Ebbe'
_publ_section_title
;
 Bis- and tris(pyridyl)amine-oxidovanadium complexes: Characteristics
 and insulin-mimetic potential
;
_journal_issue                   38
_journal_name_full               'Dalton Transactions'
_journal_page_first              7902
_journal_page_last               7911
_journal_paper_doi               10.1039/b903456k
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H19 Cl2 N3 O2 V, C H4 O'
_chemical_formula_sum            'C20 H23 Cl2 N3 O3 V'
_chemical_formula_weight         475.25
_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   mixed
_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                   8.2798(4)
_cell_length_b                   14.8063(6)
_cell_length_c                   17.2853(7)
_cell_measurement_reflns_used    6610
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2119.06(16)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Diamond v.3.1d (Brandenburg, 2006)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18593
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.9636
_exptl_absorpt_correction_T_min  0.8836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Xprep in Shelxtl v.6.14-1 (Sheldrick, 2005)'
_exptl_crystal_colour            'pale green'
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0355
_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)+(0.0339P)²+0.2772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0788
_reflns_number_gt                3897
_reflns_number_total             4826
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b903456k.txt
_cod_data_source_block           jn1046d
_cod_database_code               7002330
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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 0.45022(6) 0.97751(3) 0.06544(2) 0.02199(11) Uani 1 1 d . . .
Cl1 Cl 0.44041(10) 0.87405(4) 0.16873(4) 0.02975(16) Uani 1 1 d . . .
Cl2 Cl 0.64656(9) 1.06554(4) 0.12704(4) 0.02936(16) Uani 1 1 d . . .
O1 O 0.5563(2) 0.92310(11) 0.00365(10) 0.0281(4) Uani 1 1 d . . .
O2 O -0.0594(3) 1.02240(12) 0.26018(10) 0.0310(4) Uani 1 1 d . . .
H2O H -0.1586 1.0118 0.2726 0.046 Uiso 1 1 d R . .
O3 O 0.6378(3) 0.97920(16) 0.30159(12) 0.0445(5) Uani 1 1 d . . .
H3O H 0.6070 0.9574 0.2524 0.091(15) Uiso 1 1 d R . .
N1 N 0.2520(3) 1.07090(13) 0.12496(12) 0.0200(5) Uani 1 1 d . . .
N2 N 0.4042(3) 1.08643(14) -0.01205(12) 0.0246(5) Uani 1 1 d . . .
N3 N 0.2287(3) 0.92512(13) 0.02439(12) 0.0206(5) Uani 1 1 d . . .
C1 C 0.2559(3) 1.06555(17) 0.21140(14) 0.0226(5) Uani 1 1 d . . .
H1A H 0.3686 1.0754 0.2287 0.027 Uiso 1 1 calc R . .
H1B H 0.2249 1.0036 0.2269 0.027 Uiso 1 1 calc R . .
C2 C 0.1482(3) 1.13160(16) 0.25397(14) 0.0215(5) Uani 1 1 d . . .
C3 C -0.0085(3) 1.10857(17) 0.27552(14) 0.0244(6) Uani 1 1 d . . .
C4 C -0.1059(3) 1.17051(19) 0.31324(15) 0.0294(7) Uani 1 1 d . . .
H4 H -0.2134 1.1546 0.3267 0.035 Uiso 1 1 calc R . .
C5 C -0.0478(4) 1.25488(18) 0.33126(14) 0.0324(7) Uani 1 1 d . . .
H5 H -0.1162 1.2973 0.3563 0.039 Uiso 1 1 calc R . .
C6 C 0.1105(4) 1.27873(19) 0.31319(15) 0.0320(7) Uani 1 1 d . . .
H6 H 0.1520 1.3363 0.3272 0.038 Uiso 1 1 calc R . .
C7 C 0.2061(3) 1.21669(17) 0.27431(15) 0.0270(6) Uani 1 1 d . . .
H7 H 0.3138 1.2326 0.2612 0.032 Uiso 1 1 calc R . .
C8 C 0.2938(3) 1.16334(16) 0.09835(15) 0.0246(6) Uani 1 1 d . . .
H8A H 0.3895 1.1856 0.1269 0.030 Uiso 1 1 calc R . .
H8B H 0.2026 1.2049 0.1088 0.030 Uiso 1 1 calc R . .
C9 C 0.3291(3) 1.16156(17) 0.01343(15) 0.0241(6) Uani 1 1 d . . .
C10 C 0.4391(4) 1.07938(17) -0.08806(14) 0.0305(6) Uani 1 1 d . . .
H10 H 0.4900 1.0259 -0.1063 0.037 Uiso 1 1 calc R . .
C11 C 0.4038(4) 1.14659(19) -0.13999(17) 0.0363(7) Uani 1 1 d . . .
H11 H 0.4304 1.1399 -0.1931 0.044 Uiso 1 1 calc R . .
C12 C 0.3287(4) 1.2242(2) -0.11370(16) 0.0372(7) Uani 1 1 d . . .
H12 H 0.3034 1.2718 -0.1486 0.045 Uiso 1 1 calc R . .
C13 C 0.2907(4) 1.23180(19) -0.03592(17) 0.0340(7) Uani 1 1 d . . .
H13 H 0.2390 1.2845 -0.0168 0.041 Uiso 1 1 calc R . .
C14 C 0.0892(3) 1.04652(17) 0.09379(15) 0.0264(6) Uani 1 1 d . . .
H14A H 0.0490 1.0973 0.0619 0.032 Uiso 1 1 calc R . .
H14B H 0.0137 1.0387 0.1377 0.032 Uiso 1 1 calc R . .
C15 C 0.0874(3) 0.96190(16) 0.04566(13) 0.0208(6) Uani 1 1 d . . .
C16 C 0.2260(3) 0.85223(16) -0.02234(15) 0.0249(6) Uani 1 1 d . . .
H16 H 0.3256 0.8265 -0.0383 0.030 Uiso 1 1 calc R . .
C17 C 0.0846(4) 0.81371(18) -0.04779(16) 0.0306(6) Uani 1 1 d . . .
H17 H 0.0866 0.7621 -0.0804 0.037 Uiso 1 1 calc R . .
C18 C -0.0598(4) 0.85131(17) -0.02509(15) 0.0281(6) Uani 1 1 d . . .
H18 H -0.1590 0.8258 -0.0420 0.034 Uiso 1 1 calc R . .
C19 C -0.0596(4) 0.92626(16) 0.02232(14) 0.0241(5) Uani 1 1 d . . .
H19 H -0.1582 0.9529 0.0386 0.029 Uiso 1 1 calc R . .
C20 C 0.5992(5) 0.9188(2) 0.3613(2) 0.0587(11) Uani 1 1 d . . .
H20A H 0.6669 0.9315 0.4065 0.088 Uiso 1 1 calc R . .
H20B H 0.6184 0.8567 0.3437 0.088 Uiso 1 1 calc R . .
H20C H 0.4852 0.9258 0.3753 0.088 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'
Cl Cl 0.1484 0.1585 '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 N3 93.87(9) . . ?
O1 V1 N2 93.42(8) . . ?
N3 V1 N2 84.93(8) . . ?
O1 V1 Cl2 101.69(7) . . ?
N3 V1 Cl2 163.71(6) . . ?
N2 V1 Cl2 89.35(6) . . ?
O1 V1 Cl1 101.39(7) . . ?
N3 V1 Cl1 89.19(6) . . ?
N2 V1 Cl1 164.41(6) . . ?
Cl2 V1 Cl1 92.37(3) . . ?
O1 V1 N1 163.63(9) . . ?
N3 V1 N1 76.12(8) . . ?
N2 V1 N1 73.07(8) . . ?
Cl2 V1 N1 87.64(5) . . ?
Cl1 V1 N1 91.51(5) . . ?
C3 O2 H2O 114.5 . . ?
C20 O3 H3O 112.5 . . ?
C8 N1 C14 108.7(2) . . ?
C8 N1 C1 110.67(19) . . ?
C14 N1 C1 111.5(2) . . ?
C8 N1 V1 103.95(15) . . ?
C14 N1 V1 109.00(14) . . ?
C1 N1 V1 112.70(15) . . ?
C9 N2 C10 118.7(2) . . ?
C9 N2 V1 120.10(16) . . ?
C10 N2 V1 121.01(17) . . ?
C15 N3 C16 118.3(2) . . ?
C15 N3 V1 121.03(16) . . ?
C16 N3 V1 120.63(18) . . ?
N1 C1 C2 116.0(2) . . ?
N1 C1 H1A 108.3 . . ?
C2 C1 H1A 108.3 . . ?
N1 C1 H1B 108.3 . . ?
C2 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C3 C2 C7 118.3(2) . . ?
C3 C2 C1 121.4(2) . . ?
C7 C2 C1 120.3(2) . . ?
O2 C3 C4 121.9(2) . . ?
O2 C3 C2 117.6(2) . . ?
C4 C3 C2 120.4(2) . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 118.5(3) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C2 121.7(3) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N1 C8 C9 109.4(2) . . ?
N1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C13 121.7(2) . . ?
N2 C9 C8 115.2(2) . . ?
C13 C9 C8 123.2(2) . . ?
N2 C10 C11 122.4(2) . . ?
N2 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C12 118.9(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 119.2(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C9 C13 C12 119.1(3) . . ?
C9 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N1 C14 C15 114.2(2) . . ?
N1 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
N1 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
N3 C15 C19 122.1(2) . . ?
N3 C15 C14 118.7(2) . . ?
C19 C15 C14 119.1(2) . . ?
N3 C16 C17 122.6(3) . . ?
N3 C16 H16 118.7 . . ?
C17 C16 H16 118.7 . . ?
C16 C17 C18 118.7(2) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C17 C18 C19 119.6(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C15 118.7(3) . . ?
C18 C19 H19 120.7 . . ?
C15 C19 H19 120.7 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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
V1 O1 1.6003(18) . ?
V1 N3 2.114(2) . ?
V1 N2 2.131(2) . ?
V1 Cl2 2.3400(8) . ?
V1 Cl1 2.3540(7) . ?
V1 N1 2.380(2) . ?
O2 C3 1.370(3) . ?
O2 H2O 0.8635 . ?
O3 C20 1.402(4) . ?
O3 H3O 0.9439 . ?
N1 C8 1.485(3) . ?
N1 C14 1.496(3) . ?
N1 C1 1.497(3) . ?
N2 C9 1.348(3) . ?
N2 C10 1.349(3) . ?
N3 C15 1.342(3) . ?
N3 C16 1.348(3) . ?
C1 C2 1.515(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.392(4) . ?
C2 C7 1.393(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.374(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.497(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C13 1.382(4) . ?
C10 C11 1.372(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.504(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C19 1.387(4) . ?
C16 C17 1.374(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O3 0.86 1.82 2.685(3) 174.8 1_455
O3 H3O Cl1 0.94 2.35 3.220(2) 153.2 .
O3 H3O Cl2 0.94 2.71 3.278(2) 119.0 .
