#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/88/2218848.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2218848
loop_
_publ_author_name
'Romanowski, Grzegorz'
'Sikorski, Artur'
'Wojtczak, Andrzej'
_publ_section_title
Di-μ-oxido-bis({(R)-(--)-2-[1-(2-aminopropylimino)ethyl]-1-naphtholato-κ³N,N',O}oxidovanadium(V))
_journal_coeditor_code           XU2429
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m950
_journal_page_last               m951
_journal_paper_doi               10.1107/S160053680801787X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[V2 (C15 H17 N2 O)2 O4]'
_chemical_formula_moiety         'C30 H34 N4 O6 V2'
_chemical_formula_sum            'C30 H34 N4 O6 V2'
_chemical_formula_weight         648.49
_chemical_name_systematic
;Di-μ-oxido-bis({(R)-(-)-2-[1-(2-aminopropylimino)ethyl]-1-naphtholato-
κ³N,N',O}oxidovanadium(V))
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 118.09(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.187(5)
_cell_length_b                   7.663(2)
_cell_length_c                   16.898(3)
_cell_measurement_reflns_used    2875
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.75
_cell_volume                     2877.3(13)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Oxford Diffraction Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_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  0.0776
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9202
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  0.9182
_exptl_absorpt_correction_T_min  0.8280
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.408
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.234
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0842
_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)+(0.0144P)²+24.507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1526
_reflns_number_gt                2086
_reflns_number_total             2474
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2429.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2218848
_cod_database_fobs_code          2218848
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V V1 0.22582(5) 0.07588(12) 0.02520(6) 0.0261(3) Uani d . 1 . .
O O1 0.1947(2) -0.1142(5) 0.0042(3) 0.0419(11) Uani d . 1 . .
N N1 0.3137(2) -0.0142(6) 0.0585(3) 0.0323(12) Uani d . 1 . .
H H1A 0.3102 -0.1053 0.0226 0.039 Uiso calc R 1 A 1
H H1B 0.3330 0.0713 0.0457 0.039 Uiso calc R 1 A 1
O O2 0.28370(18) 0.3407(5) 0.0711(2) 0.0308(9) Uani d . 1 . .
C C3 0.3353(3) 0.0368(9) 0.2130(4) 0.0413(16) Uani d . 1 . .
H H3A 0.3546 0.1468 0.2393 0.050 Uiso d R 1 B .
H H3B 0.3476 -0.0479 0.2612 0.050 Uiso d R 1 . .
N N4 0.2701(2) 0.0595(6) 0.1714(3) 0.0266(10) Uani d . 1 B .
C C5 0.2442(3) 0.0737(7) 0.2207(4) 0.0307(13) Uani d . 1 . .
C C6 0.1780(3) 0.0906(7) 0.1799(4) 0.0301(13) Uani d . 1 B .
C C7 0.1481(3) 0.0356(7) 0.2291(4) 0.0361(15) Uani d . 1 . .
H H7A 0.1702 -0.0160 0.2850 0.043 Uiso calc R 1 B .
C C8 0.0877(3) 0.0571(9) 0.1958(4) 0.0413(16) Uani d . 1 B .
H H8A 0.0691 0.0174 0.2287 0.050 Uiso calc R 1 . .
C C9 0.0529(3) 0.1389(8) 0.1121(4) 0.0384(15) Uani d . 1 . .
C C10 -0.0103(3) 0.1660(9) 0.0753(5) 0.0475(18) Uani d . 1 B .
H H10A -0.0300 0.1282 0.1069 0.057 Uiso calc R 1 . .
C C11 -0.0422(3) 0.2461(10) -0.0052(6) 0.056(2) Uani d . 1 . .
H H11A -0.0834 0.2628 -0.0275 0.068 Uiso calc R 1 B .
C C12 -0.0147(3) 0.3033(10) -0.0545(5) 0.056(2) Uani d . 1 B .
H H12A -0.0370 0.3601 -0.1089 0.067 Uiso calc R 1 . .
C C13 0.0463(3) 0.2751(8) -0.0219(4) 0.0415(16) Uani d . 1 . .
H H13A 0.0646 0.3107 -0.0558 0.050 Uiso calc R 1 B .
C C14 0.0811(3) 0.1941(7) 0.0611(4) 0.0315(13) Uani d . 1 B .
C C15 0.1446(2) 0.1620(7) 0.0945(4) 0.0264(12) Uani d . 1 . .
O O16 0.16869(17) 0.2114(5) 0.0436(2) 0.0288(9) Uani d . 1 B .
C C18 0.2780(3) 0.0802(9) 0.3211(4) 0.0414(15) Uani d . 1 B .
H H18A 0.3139 0.1484 0.3397 0.062 Uiso calc R 1 . .
H H18B 0.2887 -0.0361 0.3444 0.062 Uiso calc R 1 . .
H H18C 0.2531 0.1324 0.3436 0.062 Uiso calc R 1 . .
C C2A 0.3524(5) -0.070(2) 0.1537(8) 0.042(4) Uani d P 0.54(2) B 1
H H2A 0.3435 -0.1922 0.1590 0.051 Uiso calc PR 0.54(2) B 1
C C17A 0.419(2) -0.055(6) 0.180(3) 0.067(15) Uani d P 0.54(2) B 1
H H17A 0.4422 -0.1162 0.2359 0.101 Uiso calc PR 0.54(2) B 1
H H17B 0.4306 0.0653 0.1877 0.101 Uiso calc PR 0.54(2) B 1
H H17C 0.4262 -0.1063 0.1344 0.101 Uiso calc PR 0.54(2) B 1
C C2B 0.3583(6) 0.041(3) 0.1485(9) 0.029(4) Uiso d P 0.46(2) B 2
H H2B 0.3679 0.1637 0.1437 0.034 Uiso d PR 0.46(2) B 2
C C17B 0.418(3) -0.071(6) 0.184(4) 0.046(11) Uiso d P 0.46(2) B 2
H H17D 0.4385 -0.0718 0.2485 0.069 Uiso calc PR 0.46(2) B 2
H H17E 0.4442 -0.0207 0.1630 0.069 Uiso calc PR 0.46(2) B 2
H H17F 0.4084 -0.1885 0.1622 0.069 Uiso calc PR 0.46(2) B 2
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 V1 O2 . 7 107.6(2)
O1 V1 O16 . . 101.6(2)
O2 V1 O16 7 . 100.23(18)
O1 V1 N1 . . 95.9(2)
O2 V1 N1 7 . 92.07(19)
O16 V1 N1 . . 154.36(19)
O1 V1 N4 . . 97.7(2)
O2 V1 N4 7 . 153.32(19)
O16 V1 N4 . . 82.56(17)
N1 V1 N4 . . 76.61(18)
O1 V1 O2 . . 172.50(19)
O2 V1 O2 7 . 77.09(18)
O16 V1 O2 . . 82.98(15)
N1 V1 O2 . . 77.93(17)
N4 V1 O2 . . 76.95(15)
C2B N1 V1 . . 111.9(6)
C2A N1 V1 . . 116.4(5)
C2B N1 H1A . . 135.2
C2A N1 H1A . . 108.2
V1 N1 H1A . . 108.2
C2B N1 H1B . . 78.5
C2A N1 H1B . . 108.2
V1 N1 H1B . . 108.2
H1A N1 H1B . . 107.3
V1 O2 V1 7 . 102.91(18)
C2B C3 N4 . . 112.9(7)
N4 C3 C2A . . 110.7(6)
C2B C3 H3A . . 91.7
N4 C3 H3A . . 109.0
C2A C3 H3A . . 122.4
C2B C3 H3B . . 124.2
N4 C3 H3B . . 109.1
C2A C3 H3B . . 96.8
H3A C3 H3B . . 107.7
C5 N4 C3 . . 119.9(5)
C5 N4 V1 . . 125.8(4)
C3 N4 V1 . . 114.3(3)
N4 C5 C6 . . 120.8(5)
N4 C5 C18 . . 123.2(5)
C6 C5 C18 . . 116.0(5)
C15 C6 C7 . . 119.5(5)
C15 C6 C5 . . 121.0(5)
C7 C6 C5 . . 119.6(5)
C8 C7 C6 . . 121.3(6)
C8 C7 H7A . . 119.3
C6 C7 H7A . . 119.3
C7 C8 C9 . . 120.8(6)
C7 C8 H8A . . 119.6
C9 C8 H8A . . 119.6
C14 C9 C8 . . 119.4(6)
C14 C9 C10 . . 117.9(6)
C8 C9 C10 . . 122.7(6)
C11 C10 C9 . . 121.1(7)
C11 C10 H10A . . 119.5
C9 C10 H10A . . 119.5
C10 C11 C12 . . 121.2(7)
C10 C11 H11A . . 119.4
C12 C11 H11A . . 119.4
C11 C12 C13 . . 119.3(7)
C11 C12 H12A . . 120.4
C13 C12 H12A . . 120.4
C12 C13 C14 . . 121.5(7)
C12 C13 H13A . . 119.3
C14 C13 H13A . . 119.3
C13 C14 C9 . . 119.0(6)
C13 C14 C15 . . 121.5(6)
C9 C14 C15 . . 119.5(5)
O16 C15 C6 . . 123.2(5)
O16 C15 C14 . . 117.4(5)
C6 C15 C14 . . 119.2(5)
C15 O16 V1 . . 124.1(3)
C5 C18 H18A . . 109.5
C5 C18 H18B . . 109.5
H18A C18 H18B . . 109.5
C5 C18 H18C . . 109.5
H18A C18 H18C . . 109.5
H18B C18 H18C . . 109.5
N1 C2A C3 . . 108.6(9)
N1 C2A C17A . . 111(2)
C3 C2A C17A . . 113(2)
N1 C2A H2A . . 108.0
C3 C2A H2A . . 108.0
C17A C2A H2A . . 108.0
C3 C2B N1 . . 113.0(10)
C3 C2B C17B . . 110(3)
N1 C2B C17B . . 111(2)
C3 C2B H2B . . 106.6
N1 C2B H2B . . 106.9
C17B C2B H2B . . 108.7
C2B C17B H17D . . 109.5
C2B C17B H17E . . 109.5
H17D C17B H17E . . 109.5
C2B C17B H17F . . 109.5
H17D C17B H17F . . 109.5
H17E C17B H17F . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
V1 O1 . 1.612(4)
V1 O2 7 1.658(4)
V1 O16 . 1.915(4)
V1 N1 . 2.127(5)
V1 N4 . 2.183(4)
V1 O2 . 2.404(4)
N1 C2B . 1.466(14)
N1 C2A . 1.498(13)
N1 H1A . 0.9000
N1 H1B . 0.9000
O2 V1 7 1.658(4)
C3 C2B . 1.456(14)
C3 N4 . 1.460(7)
C3 C2A . 1.502(14)
C3 H3A . 0.9700
C3 H3B . 0.9700
N4 C5 . 1.282(7)
C5 C6 . 1.479(8)
C5 C18 . 1.499(8)
C6 C15 . 1.395(8)
C6 C7 . 1.424(8)
C7 C8 . 1.360(9)
C7 H7A . 0.9300
C8 C9 . 1.413(9)
C8 H8A . 0.9300
C9 C14 . 1.413(8)
C9 C10 . 1.425(9)
C10 C11 . 1.358(11)
C10 H10A . 0.9300
C11 C12 . 1.382(10)
C11 H11A . 0.9300
C12 C13 . 1.383(9)
C12 H12A . 0.9300
C13 C14 . 1.401(9)
C13 H13A . 0.9300
C14 C15 . 1.446(8)
C15 O16 . 1.320(6)
C18 H18A . 0.9600
C18 H18B . 0.9600
C18 H18C . 0.9600
C2A C17A . 1.52(6)
C2A H2A . 0.9800
C17A H17A . 0.9600
C17A H17B . 0.9600
C17A H17C . 0.9600
C2B C17B . 1.59(6)
C2B H2B . 0.9800
C17B H17D . 0.9600
C17B H17E . 0.9600
C17B H17F . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O1 1_555 1_555 7_545 0.90 2.19 3.011(6) 151 y
C7 H7A O2 1_555 1_555 4_545 0.93 2.41 3.335(7) 173 y
C18 H18B O16 1_555 1_555 4_545 0.96 2.56 3.482(8) 161 y
C3 H3B Cg1 1_555 1_555 4_545 0.97 2.95 3.874(7) 159 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O1 V1 N1 C2B . . -123.4(9)
O2 V1 N1 C2B 7 . 128.7(9)
O16 V1 N1 C2B . . 9.6(10)
N4 V1 N1 C2B . . -26.9(9)
O2 V1 N1 C2B . . 52.3(9)
O1 V1 N1 C2A . . -86.0(9)
O2 V1 N1 C2A 7 . 166.1(9)
O16 V1 N1 C2A . . 47.0(10)
N4 V1 N1 C2A . . 10.5(9)
O2 V1 N1 C2A . . 89.8(9)
O2 V1 O2 V1 7 7 0.0
O16 V1 O2 V1 . 7 -102.2(2)
N1 V1 O2 V1 . 7 95.0(2)
N4 V1 O2 V1 . 7 173.8(2)
C2B C3 N4 C5 . . -173.8(10)
C2A C3 N4 C5 . . 149.1(9)
C2B C3 N4 V1 . . 3.9(10)
C2A C3 N4 V1 . . -33.1(9)
O1 V1 N4 C5 . . -75.5(5)
O2 V1 N4 C5 7 . 123.3(5)
O16 V1 N4 C5 . . 25.3(5)
N1 V1 N4 C5 . . -169.7(5)
O2 V1 N4 C5 . . 109.8(5)
O1 V1 N4 C3 . . 106.9(4)
O2 V1 N4 C3 7 . -54.3(6)
O16 V1 N4 C3 . . -152.3(4)
N1 V1 N4 C3 . . 12.7(4)
O2 V1 N4 C3 . . -67.8(4)
C3 N4 C5 C6 . . -177.8(5)
V1 N4 C5 C6 . . 4.7(8)
C3 N4 C5 C18 . . 4.2(9)
V1 N4 C5 C18 . . -173.3(4)
N4 C5 C6 C15 . . -26.7(8)
C18 C5 C6 C15 . . 151.4(6)
N4 C5 C6 C7 . . 154.3(6)
C18 C5 C6 C7 . . -27.6(8)
C15 C6 C7 C8 . . -2.4(9)
C5 C6 C7 C8 . . 176.6(6)
C6 C7 C8 C9 . . -1.6(10)
C7 C8 C9 C14 . . 2.0(10)
C7 C8 C9 C10 . . -179.2(6)
C14 C9 C10 C11 . . -1.6(10)
C8 C9 C10 C11 . . 179.6(7)
C9 C10 C11 C12 . . 0.4(11)
C10 C11 C12 C13 . . 1.3(12)
C11 C12 C13 C14 . . -1.8(11)
C12 C13 C14 C9 . . 0.6(10)
C12 C13 C14 C15 . . 179.0(6)
C8 C9 C14 C13 . . 180.0(6)
C10 C9 C14 C13 . . 1.1(9)
C8 C9 C14 C15 . . 1.5(9)
C10 C9 C14 C15 . . -177.4(6)
C7 C6 C15 O16 . . -178.0(5)
C5 C6 C15 O16 . . 3.1(8)
C7 C6 C15 C14 . . 5.8(8)
C5 C6 C15 C14 . . -173.2(5)
C13 C14 C15 O16 . . -0.3(8)
C9 C14 C15 O16 . . 178.1(5)
C13 C14 C15 C6 . . 176.2(5)
C9 C14 C15 C6 . . -5.4(8)
C6 C15 O16 V1 . . 45.4(7)
C14 C15 O16 V1 . . -138.3(4)
O1 V1 O16 C15 . . 47.0(4)
O2 V1 O16 C15 7 . 157.5(4)
N1 V1 O16 C15 . . -85.1(6)
N4 V1 O16 C15 . . -49.4(4)
O2 V1 O16 C15 . . -127.0(4)
C2B N1 C2A C3 . . 59.9(13)
V1 N1 C2A C3 . . -30.7(14)
C2B N1 C2A C17A . . -65(2)
V1 N1 C2A C17A . . -155(2)
C2B C3 C2A N1 . . -60.6(12)
N4 C3 C2A N1 . . 40.1(13)
C2B C3 C2A C17A . . 63(2)
N4 C3 C2A C17A . . 164(2)
N4 C3 C2B N1 . . -27.1(16)
C2A C3 C2B N1 . . 66.4(14)
N4 C3 C2B C17B . . -152.1(19)
C2A C3 C2B C17B . . -59(2)
C2A N1 C2B C3 . . -66.9(14)
V1 N1 C2B C3 . . 38.2(15)
C2A N1 C2B C17B . . 58(3)
V1 N1 C2B C17B . . 163(3)
