#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227030.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_2227030
loop_
_publ_author_name
'Wong, Hon Wee'
'Lo, Kong Mun'
'Ng, Seik Weng'
_publ_section_title
;
 (Acetylacetone
 3-hydroxy-2-naphthoylhydrazonato-κ³O,N',O')(methoxo-κO)oxidovanadate(V)
;
_journal_coeditor_code           NK2050
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1021
_journal_paper_doi               10.1107/S1600536810028898
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[V (C16 H14 N2 O3) (C H3 O) O]'
_chemical_formula_moiety         'C17 H17 N2 O5 V'
_chemical_formula_sum            'C17 H17 N2 O5 V'
_chemical_formula_weight         380.27
_chemical_name_systematic
;
(Acetylacetone
3-hydroxy-2-naphthoylhydrazonato-κ³O,N',O')(methoxo-
κO)oxidovanadate(V)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.6180(10)
_cell_angle_beta                 70.8210(10)
_cell_angle_gamma                85.9740(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7379(8)
_cell_length_b                   9.7753(10)
_cell_length_c                   11.4411(11)
_cell_measurement_reflns_used    2783
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      2.8
_cell_volume                     814.77(14)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7840
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.9388
_exptl_absorpt_correction_T_min  0.8312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.416
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3716
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0499P)²+0.2795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                3013
_reflns_number_total             3716
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nk2050.cif
_cod_data_source_block           I
_cod_database_code               2227030
_cod_database_fobs_code          2227030
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 1.03271(5) 0.59868(4) 0.20412(3) 0.01980(12) Uani d . 1 . .
O O1 1.23385(19) 0.48290(15) 0.12970(13) 0.0226(3) Uani d . 1 . .
O O2 0.90127(19) 0.68028(15) 0.35967(13) 0.0215(3) Uani d . 1 . .
O O3 0.5685(2) 0.44133(16) 0.65797(15) 0.0270(4) Uani d D 1 . .
H H3 0.642(3) 0.413(3) 0.5925(17) 0.052(9) Uiso d D 1 . .
O O4 0.8957(2) 0.58562(17) 0.12891(14) 0.0268(4) Uani d . 1 . .
O O5 1.1345(2) 0.75747(15) 0.15366(13) 0.0242(3) Uani d . 1 . .
N N1 0.9533(2) 0.43490(19) 0.32837(15) 0.0200(4) Uani d . 1 . .
N N2 0.8269(2) 0.46643(18) 0.44290(15) 0.0197(4) Uani d . 1 . .
C C1 1.4016(3) 0.3021(2) 0.0049(2) 0.0262(5) Uani d . 1 . .
H H1A 1.5157 0.3390 0.0056 0.039 Uiso calc R 1 . .
H H1B 1.3764 0.3345 -0.0709 0.039 Uiso calc R 1 . .
H H1C 1.4138 0.2016 0.0077 0.039 Uiso calc R 1 . .
C C2 1.2480(3) 0.3493(2) 0.11473(19) 0.0226(5) Uani d . 1 . .
C C3 1.1325(3) 0.2624(2) 0.1970(2) 0.0237(5) Uani d . 1 . .
H H3a 1.1440 0.1681 0.1786 0.028 Uiso calc R 1 . .
C C4 0.9969(3) 0.3040(2) 0.30769(19) 0.0211(4) Uani d . 1 . .
C C5 0.9049(3) 0.1972(2) 0.4039(2) 0.0246(5) Uani d . 1 . .
H H5A 0.7716 0.2123 0.4263 0.037 Uiso calc R 1 . .
H H5B 0.9413 0.2040 0.4776 0.037 Uiso calc R 1 . .
H H5C 0.9418 0.1057 0.3704 0.037 Uiso calc R 1 . .
C C6 0.8042(3) 0.5988(2) 0.45013(18) 0.0197(4) Uani d . 1 . .
C C7 0.6691(3) 0.6619(2) 0.55786(18) 0.0191(4) Uani d . 1 . .
C C8 0.5524(3) 0.5805(2) 0.65770(19) 0.0202(4) Uani d . 1 . .
C C9 0.4232(3) 0.6431(2) 0.75423(19) 0.0213(4) Uani d . 1 . .
H H9 0.3474 0.5883 0.8199 0.026 Uiso calc R 1 . .
C C10 0.3994(3) 0.7875(2) 0.75869(19) 0.0197(4) Uani d . 1 . .
C C11 0.2617(3) 0.8555(2) 0.8555(2) 0.0240(5) Uani d . 1 . .
H H11 0.1839 0.8029 0.9221 0.029 Uiso calc R 1 . .
C C12 0.2394(3) 0.9953(2) 0.8542(2) 0.0262(5) Uani d . 1 . .
H H12 0.1459 1.0386 0.9197 0.031 Uiso calc R 1 . .
C C13 0.3529(3) 1.0762(2) 0.7572(2) 0.0257(5) Uani d . 1 . .
H H13 0.3356 1.1733 0.7572 0.031 Uiso calc R 1 . .
C C14 0.4881(3) 1.0143(2) 0.6631(2) 0.0227(5) Uani d . 1 . .
H H14 0.5653 1.0692 0.5982 0.027 Uiso calc R 1 . .
C C15 0.5148(3) 0.8695(2) 0.66085(18) 0.0187(4) Uani d . 1 . .
C C16 0.6479(3) 0.8029(2) 0.56254(18) 0.0194(4) Uani d . 1 . .
H H16 0.7259 0.8569 0.4972 0.023 Uiso calc R 1 . .
C C17 1.2231(3) 0.8381(2) 0.2134(2) 0.0286(5) Uani d . 1 . .
H H17A 1.1333 0.8741 0.2889 0.043 Uiso calc R 1 . .
H H17B 1.2789 0.9146 0.1577 0.043 Uiso calc R 1 . .
H H17C 1.3185 0.7813 0.2350 0.043 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 V1 O5 . . 105.62(8) ?
O4 V1 O1 . . 105.47(8) ?
O5 V1 O1 . . 98.56(7) ?
O4 V1 O2 . . 108.97(7) ?
O5 V1 O2 . . 87.78(6) ?
O1 V1 O2 . . 141.78(6) ?
O4 V1 N1 . . 98.68(7) ?
O5 V1 N1 . . 153.82(7) ?
O1 V1 N1 . . 83.93(7) ?
O2 V1 N1 . . 75.08(7) ?
C2 O1 V1 . . 131.01(13) ?
C6 O2 V1 . . 117.27(13) ?
C8 O3 H3 . . 112(2) ?
C17 O5 V1 . . 128.78(13) ?
C4 N1 N2 . . 116.69(17) ?
C4 N1 V1 . . 127.25(14) ?
N2 N1 V1 . . 115.79(13) ?
C6 N2 N1 . . 108.95(17) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 C3 . . 121.7(2) ?
O1 C2 C1 . . 114.88(19) ?
C3 C2 C1 . . 123.4(2) ?
C2 C3 C4 . . 124.2(2) ?
C2 C3 H3a . . 117.9 ?
C4 C3 H3a . . 117.9 ?
N1 C4 C3 . . 120.71(19) ?
N1 C4 C5 . . 119.81(19) ?
C3 C4 C5 . . 119.47(19) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N2 C6 O2 . . 120.77(19) ?
N2 C6 C7 . . 121.02(18) ?
O2 C6 C7 . . 118.20(18) ?
C16 C7 C8 . . 118.74(19) ?
C16 C7 C6 . . 119.59(18) ?
C8 C7 C6 . . 121.63(19) ?
O3 C8 C9 . . 118.97(19) ?
O3 C8 C7 . . 121.06(19) ?
C9 C8 C7 . . 120.0(2) ?
C8 C9 C10 . . 121.51(19) ?
C8 C9 H9 . . 119.2 ?
C10 C9 H9 . . 119.2 ?
C9 C10 C11 . . 122.76(19) ?
C9 C10 C15 . . 119.14(19) ?
C11 C10 C15 . . 118.09(19) ?
C12 C11 C10 . . 120.9(2) ?
C12 C11 H11 . . 119.5 ?
C10 C11 H11 . . 119.5 ?
C11 C12 C13 . . 121.0(2) ?
C11 C12 H12 . . 119.5 ?
C13 C12 H12 . . 119.5 ?
C14 C13 C12 . . 119.7(2) ?
C14 C13 H13 . . 120.1 ?
C12 C13 H13 . . 120.1 ?
C13 C14 C15 . . 120.9(2) ?
C13 C14 H14 . . 119.5 ?
C15 C14 H14 . . 119.5 ?
C16 C15 C14 . . 122.15(19) ?
C16 C15 C10 . . 118.45(19) ?
C14 C15 C10 . . 119.37(19) ?
C7 C16 C15 . . 122.19(18) ?
C7 C16 H16 . . 118.9 ?
C15 C16 H16 . . 118.9 ?
O5 C17 H17A . . 109.5 ?
O5 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O5 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 O4 . 1.5850(15) ?
V1 O5 . 1.7693(15) ?
V1 O1 . 1.8504(15) ?
V1 O2 . 1.9242(15) ?
V1 N1 . 2.0632(17) ?
O1 C2 . 1.319(3) ?
O2 C6 . 1.322(2) ?
O3 C8 . 1.357(3) ?
O3 H3 . 0.828(10) ?
O5 C17 . 1.416(3) ?
N1 C4 . 1.315(3) ?
N1 N2 . 1.390(2) ?
N2 C6 . 1.297(3) ?
C1 C2 . 1.488(3) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 C3 . 1.366(3) ?
C3 C4 . 1.414(3) ?
C3 H3a . 0.9500 ?
C4 C5 . 1.504(3) ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 C7 . 1.465(3) ?
C7 C16 . 1.378(3) ?
C7 C8 . 1.439(3) ?
C8 C9 . 1.365(3) ?
C9 C10 . 1.412(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.420(3) ?
C10 C15 . 1.425(3) ?
C11 C12 . 1.365(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.408(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.367(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.417(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.408(3) ?
C16 H16 . 0.9500 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_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
O3 H3 N2 . 0.830(10) 1.91(2) 2.623(2) 144(3) yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O4 V1 O1 C2 . . . . -60.18(18) ?
O5 V1 O1 C2 . . . . -169.10(17) ?
O2 V1 O1 C2 . . . . 93.57(19) ?
N1 V1 O1 C2 . . . . 37.18(17) ?
O4 V1 O2 C6 . . . . 81.17(14) ?
O5 V1 O2 C6 . . . . -173.06(14) ?
O1 V1 O2 C6 . . . . -72.03(17) ?
N1 V1 O2 C6 . . . . -13.05(13) ?
O4 V1 O5 C17 . . . . 159.55(17) ?
O1 V1 O5 C17 . . . . -91.66(18) ?
O2 V1 O5 C17 . . . . 50.46(17) ?
N1 V1 O5 C17 . . . . 2.0(3) ?
O4 V1 N1 C4 . . . . 77.84(18) ?
O5 V1 N1 C4 . . . . -124.0(2) ?
O1 V1 N1 C4 . . . . -26.94(17) ?
O2 V1 N1 C4 . . . . -174.72(18) ?
O4 V1 N1 N2 . . . . -95.99(14) ?
O5 V1 N1 N2 . . . . 62.2(2) ?
O1 V1 N1 N2 . . . . 159.23(13) ?
O2 V1 N1 N2 . . . . 11.45(12) ?
C4 N1 N2 C6 . . . . 177.68(17) ?
V1 N1 N2 C6 . . . . -7.82(19) ?
V1 O1 C2 C3 . . . . -29.6(3) ?
V1 O1 C2 C1 . . . . 152.33(15) ?
O1 C2 C3 C4 . . . . -4.0(3) ?
C1 C2 C3 C4 . . . . 173.90(19) ?
N2 N1 C4 C3 . . . . -176.11(17) ?
V1 N1 C4 C3 . . . . 10.1(3) ?
N2 N1 C4 C5 . . . . 2.5(3) ?
V1 N1 C4 C5 . . . . -171.27(14) ?
C2 C3 C4 N1 . . . . 11.5(3) ?
C2 C3 C4 C5 . . . . -167.2(2) ?
N1 N2 C6 O2 . . . . -3.3(2) ?
N1 N2 C6 C7 . . . . 175.95(16) ?
V1 O2 C6 N2 . . . . 13.9(2) ?
V1 O2 C6 C7 . . . . -165.34(13) ?
N2 C6 C7 C16 . . . . -179.81(18) ?
O2 C6 C7 C16 . . . . -0.5(3) ?
N2 C6 C7 C8 . . . . -2.0(3) ?
O2 C6 C7 C8 . . . . 177.25(17) ?
C16 C7 C8 O3 . . . . -179.55(18) ?
C6 C7 C8 O3 . . . . 2.6(3) ?
C16 C7 C8 C9 . . . . 0.4(3) ?
C6 C7 C8 C9 . . . . -177.42(18) ?
O3 C8 C9 C10 . . . . -179.64(18) ?
C7 C8 C9 C10 . . . . 0.4(3) ?
C8 C9 C10 C11 . . . . 177.58(19) ?
C8 C9 C10 C15 . . . . -0.8(3) ?
C9 C10 C11 C12 . . . . -177.81(19) ?
C15 C10 C11 C12 . . . . 0.6(3) ?
C10 C11 C12 C13 . . . . -0.3(3) ?
C11 C12 C13 C14 . . . . -0.3(3) ?
C12 C13 C14 C15 . . . . 0.7(3) ?
C13 C14 C15 C16 . . . . 177.35(19) ?
C13 C14 C15 C10 . . . . -0.4(3) ?
C9 C10 C15 C16 . . . . 0.4(3) ?
C11 C10 C15 C16 . . . . -178.07(18) ?
C9 C10 C15 C14 . . . . 178.22(18) ?
C11 C10 C15 C14 . . . . -0.3(3) ?
C8 C7 C16 C15 . . . . -0.8(3) ?
C6 C7 C16 C15 . . . . 177.05(18) ?
C14 C15 C16 C7 . . . . -177.34(19) ?
C10 C15 C16 C7 . . . . 0.4(3) ?
