#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/98/2229809.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_2229809
loop_
_publ_author_name
'Wang, Fu-Ming'
_publ_section_title
;
 [N'-(5-Bromo-2-oxidobenzylidene-κO)-2-chlorobenzohydrazidato-κ²N',O](methanol-κO)(methanolato-κO)oxidovanadium(V)
;
_journal_coeditor_code           QM2003
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m433
_journal_page_last               m434
_journal_paper_doi               10.1107/S1600536811008774
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac
'[V (C14 H8 Br Cl N2 O2) (C H3 O) O (C H4 O)]'
_chemical_formula_moiety         'C16 H15 Br Cl N2 O5 V'
_chemical_formula_sum            'C16 H15 Br Cl N2 O5 V'
_chemical_formula_weight         481.60
_chemical_name_systematic
;
[N'-(5-Bromo-2-oxidobenzylidene-κO)-2-
chlorobenzohydrazidato-κ²N',O](methanol-
κO)(methanolato-κO)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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 121.854(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.09(2)
_cell_length_b                   7.992(6)
_cell_length_c                   20.163(14)
_cell_measurement_reflns_used    1798
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.3
_cell_volume                     3845(5)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0882
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9750
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.762
_exptl_absorpt_correction_T_max  0.5691
_exptl_absorpt_correction_T_min  0.4912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.442
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4081
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0448
_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)+(0.0359P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                2266
_reflns_number_total             4081
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2003.cif
_cod_data_source_block           I
_cod_original_cell_volume        3844(5)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2229809
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 0.33992(3) 0.48966(10) 0.15964(4) 0.0355(2) Uani d . 1 . .
Br Br1 0.05406(2) 0.13036(7) 0.00218(3) 0.05439(19) Uani d . 1 . .
Cl Cl1 0.44356(6) 0.87745(17) 0.12452(7) 0.0663(4) Uani d . 1 . .
H H5 0.2799(16) 0.809(6) 0.1145(18) 0.099 Uiso d D 1 . .
N N1 0.27232(13) 0.5095(4) 0.04108(16) 0.0281(8) Uani d . 1 . .
N N2 0.28364(14) 0.5947(4) -0.01011(18) 0.0306(8) Uani d . 1 . .
O O1 0.28365(12) 0.4401(4) 0.17896(15) 0.0428(8) Uani d . 1 . .
O O2 0.37010(11) 0.6037(3) 0.10369(15) 0.0392(8) Uani d . 1 . .
O O3 0.39495(11) 0.5587(4) 0.25184(14) 0.0418(8) Uani d . 1 . .
O O4 0.35806(13) 0.3060(4) 0.15302(15) 0.0519(9) Uani d . 1 . .
O O5 0.30672(12) 0.7684(4) 0.15650(16) 0.0441(8) Uani d D 1 . .
C C1 0.20329(17) 0.3624(5) 0.0557(2) 0.0298(10) Uani d . 1 . .
C C2 0.23468(17) 0.3619(5) 0.1384(2) 0.0336(10) Uani d . 1 . .
C C3 0.21228(18) 0.2811(6) 0.1779(2) 0.0425(12) Uani d . 1 . .
H H3 0.2332 0.2758 0.2321 0.051 Uiso calc R 1 . .
C C4 0.15989(18) 0.2100(6) 0.1374(2) 0.0422(12) Uani d . 1 . .
H H4 0.1456 0.1574 0.1644 0.051 Uiso calc R 1 . .
C C5 0.12819(16) 0.2159(5) 0.0566(2) 0.0351(11) Uani d . 1 . .
C C6 0.14949(17) 0.2896(5) 0.0161(2) 0.0346(11) Uani d . 1 . .
H H6 0.1281 0.2914 -0.0382 0.042 Uiso calc R 1 . .
C C7 0.22241(18) 0.4472(5) 0.0110(2) 0.0331(10) Uani d . 1 . .
H H7 0.1975 0.4580 -0.0426 0.040 Uiso calc R 1 . .
C C8 0.33695(17) 0.6358(5) 0.0297(2) 0.0309(10) Uani d . 1 . .
C C9 0.36154(17) 0.7211(5) -0.0115(2) 0.0310(10) Uani d . 1 . .
C C10 0.40956(18) 0.8227(5) 0.0260(2) 0.0393(11) Uani d . 1 . .
C C11 0.43223(19) 0.8885(6) -0.0144(3) 0.0482(13) Uani d . 1 . .
H H11 0.4648 0.9521 0.0118 0.058 Uiso calc R 1 . .
C C12 0.4068(2) 0.8607(6) -0.0937(3) 0.0546(14) Uani d . 1 . .
H H12 0.4218 0.9076 -0.1210 0.065 Uiso calc R 1 . .
C C13 0.3589(2) 0.7628(6) -0.1326(3) 0.0530(13) Uani d . 1 . .
H H13 0.3420 0.7419 -0.1857 0.064 Uiso calc R 1 . .
C C14 0.33694(17) 0.6971(5) -0.0914(2) 0.0393(11) Uani d . 1 . .
H H14 0.3043 0.6340 -0.1180 0.047 Uiso calc R 1 . .
C C15 0.44932(19) 0.4960(8) 0.3020(3) 0.0801(19) Uani d . 1 . .
H H15A 0.4502 0.3791 0.2918 0.120 Uiso calc R 1 . .
H H15B 0.4597 0.5109 0.3552 0.120 Uiso calc R 1 . .
H H15C 0.4752 0.5552 0.2932 0.120 Uiso calc R 1 . .
C C16 0.3407(2) 0.9086(6) 0.1983(3) 0.0563(14) Uani d . 1 . .
H H16A 0.3700 0.8736 0.2494 0.084 Uiso calc R 1 . .
H H16B 0.3181 0.9920 0.2030 0.084 Uiso calc R 1 . .
H H16C 0.3569 0.9547 0.1706 0.084 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 O3 . . 103.70(15) y
O4 V1 O1 . . 99.61(15) y
O3 V1 O1 . . 102.39(13) y
O4 V1 O2 . . 97.29(14) y
O3 V1 O2 . . 93.25(13) y
O1 V1 O2 . . 153.46(12) y
O4 V1 N1 . . 96.33(13) y
O3 V1 N1 . . 157.41(14) y
O1 V1 N1 . . 84.17(13) y
O2 V1 N1 . . 73.72(13) y
O4 V1 O5 . . 174.59(12) y
O3 V1 O5 . . 81.36(12) y
O1 V1 O5 . . 80.92(13) y
O2 V1 O5 . . 80.39(12) y
N1 V1 O5 . . 78.35(11) y
C7 N1 N2 . . 116.7(3) ?
C7 N1 V1 . . 126.8(3) ?
N2 N1 V1 . . 116.5(2) ?
C8 N2 N1 . . 107.4(3) ?
C2 O1 V1 . . 133.7(3) ?
C8 O2 V1 . . 119.2(2) ?
C15 O3 V1 . . 131.4(3) ?
C16 O5 V1 . . 125.8(3) ?
C16 O5 H5 . . 105(4) ?
V1 O5 H5 . . 121(4) ?
C6 C1 C2 . . 118.7(4) ?
C6 C1 C7 . . 118.8(3) ?
C2 C1 C7 . . 122.2(4) ?
O1 C2 C3 . . 119.7(4) ?
O1 C2 C1 . . 121.4(3) ?
C3 C2 C1 . . 118.8(4) ?
C4 C3 C2 . . 120.9(4) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C3 C4 C5 . . 120.5(4) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C6 C5 C4 . . 120.2(4) ?
C6 C5 Br1 . . 120.0(3) ?
C4 C5 Br1 . . 119.8(3) ?
C5 C6 C1 . . 120.9(4) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.6 ?
N1 C7 C1 . . 123.8(4) ?
N1 C7 H7 . . 118.1 ?
C1 C7 H7 . . 118.1 ?
O2 C8 N2 . . 123.2(3) ?
O2 C8 C9 . . 117.8(4) ?
N2 C8 C9 . . 119.1(4) ?
C14 C9 C10 . . 116.9(4) ?
C14 C9 C8 . . 119.2(4) ?
C10 C9 C8 . . 123.9(4) ?
C11 C10 C9 . . 121.1(4) ?
C11 C10 Cl1 . . 115.6(4) ?
C9 C10 Cl1 . . 123.4(3) ?
C10 C11 C12 . . 120.4(4) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C11 C12 C13 . . 119.9(4) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C14 C13 C12 . . 119.0(4) ?
C14 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
C13 C14 C9 . . 122.7(4) ?
C13 C14 H14 . . 118.7 ?
C9 C14 H14 . . 118.7 ?
O3 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O5 C16 H16A . . 109.5 ?
O5 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O5 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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 . 1.582(3) y
V1 O3 . 1.765(3) y
V1 O1 . 1.859(3) y
V1 O2 . 1.957(3) y
V1 N1 . 2.134(3) y
V1 O5 . 2.403(4) y
Br1 C5 . 1.896(4) ?
Cl1 C10 . 1.746(4) ?
N1 C7 . 1.298(5) ?
N1 N2 . 1.406(4) ?
N2 C8 . 1.314(5) ?
O1 C2 . 1.328(5) ?
O2 C8 . 1.301(4) ?
O3 C15 . 1.406(5) ?
O5 C16 . 1.424(5) ?
O5 H5 . 0.85(4) ?
C1 C6 . 1.409(5) ?
C1 C2 . 1.418(5) ?
C1 C7 . 1.439(5) ?
C2 C3 . 1.404(5) ?
C3 C4 . 1.374(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.384(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.374(5) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.496(5) ?
C9 C14 . 1.390(5) ?
C9 C10 . 1.405(6) ?
C10 C11 . 1.375(6) ?
C11 C12 . 1.383(6) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.386(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.375(5) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 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_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O5 H5 N2 7_565 0.85(4) 2.06(4) 2.906(4) 178(5)
