#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/83/2228380.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_2228380
loop_
_publ_author_name
'Wong, Hon Wee'
'Lo, Kong Mun'
'Ng, Seik Weng'
_publ_section_title
;
 (4-Chlorobenzohydrazidato-κ²N',O)[2-(4-chlorobenzoylhydrazinylidene-κ²N¹,O)-3-phenylpropionato(2{-})-κO¹]oxidovanadium(V)
 methanol monosolvate
;
_journal_coeditor_code           HG2740
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1558
_journal_paper_doi               10.1107/S1600536810045678
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'[V (C7 H6 Cl N2 O) (C16 H11 Cl N2 O3) O], C H4 O'
_chemical_formula_moiety         'C23 H17 Cl2 N4 O5 V, C H4 O'
_chemical_formula_sum            'C24 H21 Cl2 N4 O6 V'
_chemical_formula_weight         583.29
_chemical_name_systematic
;
(4-Chlorobenzohydrazidato-κ²N',O)[2-(4-
chlorobenzoylhydrazinylidene-κ²N¹,O)-
3-phenylpropionato(2-)-κO¹]oxidovanadium(V) methanol monosolvate
;
_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                109.4045(7)
_cell_angle_beta                 98.8890(7)
_cell_angle_gamma                111.6936(7)
_cell_formula_units_Z            2
_cell_length_a                   8.3217(4)
_cell_length_b                   11.2505(6)
_cell_length_c                   15.5064(8)
_cell_measurement_reflns_used    8039
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.6
_cell_volume                     1206.93(11)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15037
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  0.9349
_exptl_absorpt_correction_T_min  0.8214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.852
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0375
_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)+(0.0658P)²+1.2158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                4907
_reflns_number_total             5517
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2740.cif
_cod_data_source_block           I
_cod_database_code               2228380
_cod_database_fobs_code          2228380
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 0.70290(4) 0.70483(4) 0.70065(2) 0.01467(10) Uani d . 1 . .
Cl Cl1 1.70732(7) 1.31564(6) 1.15657(4) 0.02577(14) Uani d . 1 . .
Cl Cl2 0.91329(8) 0.00311(6) 0.37080(4) 0.02773(14) Uani d . 1 . .
O O1 0.47185(19) 0.53272(15) 0.66919(10) 0.0174(3) Uani d . 1 . .
O O2 0.3293(2) 0.35991(16) 0.71185(11) 0.0225(3) Uani d . 1 . .
O O3 0.95256(19) 0.84331(15) 0.78583(10) 0.0179(3) Uani d . 1 . .
O O4 0.8120(2) 0.54984(16) 0.65625(10) 0.0185(3) Uani d . 1 . .
O O5 0.6190(2) 0.81279(16) 0.70892(11) 0.0204(3) Uani d . 1 . .
O O6 0.4172(3) 0.2179(3) 0.54539(15) 0.0477(5) Uani d . 1 . .
H H6 0.3470 0.2073 0.5787 0.072 Uiso calc R 1 . .
N N1 0.7353(2) 0.66447(18) 0.82203(12) 0.0151(3) Uani d . 1 . .
N N2 0.8951(2) 0.75265(18) 0.89745(12) 0.0167(3) Uani d . 1 . .
N N3 0.7294(2) 0.56220(19) 0.51836(12) 0.0174(3) Uani d . 1 . .
H H3 0.7125 0.5358 0.4562 0.021 Uiso calc R 1 . .
N N4 0.6962(2) 0.66803(18) 0.57236(12) 0.0174(3) Uani d . 1 . .
H H4 0.6710 0.7206 0.5467 0.021 Uiso calc R 1 . .
C C1 0.4566(3) 0.4711(2) 0.72789(14) 0.0171(4) Uani d . 1 . .
C C2 0.6167(3) 0.5496(2) 0.81905(14) 0.0162(4) Uani d . 1 . .
C C3 0.6358(3) 0.4883(2) 0.88969(15) 0.0193(4) Uani d . 1 . .
H H3A 0.5156 0.4400 0.8968 0.023 Uiso calc R 1 . .
H H3B 0.7195 0.5644 0.9535 0.023 Uiso calc R 1 . .
C C4 0.7112(3) 0.3833(2) 0.85310(15) 0.0196(4) Uani d . 1 . .
C C5 0.8986(3) 0.4305(3) 0.87107(18) 0.0266(5) Uani d . 1 . .
H H5 0.9795 0.5281 0.9077 0.032 Uiso calc R 1 . .
C C6 0.9674(4) 0.3354(3) 0.8356(2) 0.0347(6) Uani d . 1 . .
H H6A 1.0952 0.3683 0.8482 0.042 Uiso calc R 1 . .
C C7 0.8502(4) 0.1930(3) 0.7821(2) 0.0364(6) Uani d . 1 . .
H H7 0.8976 0.1281 0.7587 0.044 Uiso calc R 1 . .
C C8 0.6639(4) 0.1455(3) 0.76274(19) 0.0333(6) Uani d . 1 . .
H H8 0.5833 0.0479 0.7255 0.040 Uiso calc R 1 . .
C C9 0.5945(3) 0.2402(2) 0.79772(17) 0.0262(5) Uani d . 1 . .
H H9 0.4665 0.2071 0.7838 0.031 Uiso calc R 1 . .
C C10 0.9974(3) 0.8461(2) 0.87082(14) 0.0162(4) Uani d . 1 . .
C C11 1.1731(3) 0.9611(2) 0.94136(14) 0.0172(4) Uani d . 1 . .
C C12 1.2677(3) 1.0766(2) 0.92264(15) 0.0202(4) Uani d . 1 . .
H H12 1.2197 1.0797 0.8642 0.024 Uiso calc R 1 . .
C C13 1.4313(3) 1.1865(2) 0.98931(16) 0.0216(4) Uani d . 1 . .
H H13 1.4952 1.2659 0.9774 0.026 Uiso calc R 1 . .
C C14 1.4999(3) 1.1790(2) 1.07313(15) 0.0196(4) Uani d . 1 . .
C C15 1.4091(3) 1.0649(2) 1.09321(15) 0.0200(4) Uani d . 1 . .
H H15 1.4592 1.0613 1.1511 0.024 Uiso calc R 1 . .
C C16 1.2445(3) 0.9567(2) 1.02717(15) 0.0184(4) Uani d . 1 . .
H H16 1.1795 0.8789 1.0403 0.022 Uiso calc R 1 . .
C C17 0.7901(3) 0.5014(2) 0.56797(14) 0.0172(4) Uani d . 1 . .
C C18 0.8251(3) 0.3815(2) 0.51698(15) 0.0173(4) Uani d . 1 . .
C C19 0.8981(3) 0.3266(3) 0.57203(16) 0.0249(5) Uani d . 1 . .
H H19 0.9271 0.3685 0.6402 0.030 Uiso calc R 1 . .
C C20 0.9286(3) 0.2114(3) 0.52785(17) 0.0272(5) Uani d . 1 . .
H H20 0.9789 0.1740 0.5651 0.033 Uiso calc R 1 . .
C C21 0.8842(3) 0.1515(2) 0.42783(16) 0.0209(4) Uani d . 1 . .
C C22 0.8150(3) 0.2059(2) 0.37210(15) 0.0187(4) Uani d . 1 . .
H H22 0.7878 0.1646 0.3041 0.022 Uiso calc R 1 . .
C C23 0.7861(3) 0.3220(2) 0.41712(14) 0.0173(4) Uani d . 1 . .
H H23 0.7395 0.3610 0.3798 0.021 Uiso calc R 1 . .
C C24 0.4283(7) 0.1015(6) 0.5053(4) 0.0873(15) Uani d . 1 . .
H H24A 0.4884 0.1067 0.4561 0.131 Uiso calc R 1 . .
H H24B 0.3056 0.0221 0.4750 0.131 Uiso calc R 1 . .
H H24C 0.4994 0.0876 0.5543 0.131 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'
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
O5 V1 N4 . . 93.72(8) ?
O5 V1 O3 . . 97.65(7) ?
N4 V1 O3 . . 108.53(7) ?
O5 V1 O1 . . 98.01(7) ?
N4 V1 O1 . . 96.05(7) ?
O3 V1 O1 . . 149.78(6) ?
O5 V1 N1 . . 112.76(7) ?
N4 V1 N1 . . 152.97(7) ?
O3 V1 N1 . . 74.45(6) ?
O1 V1 N1 . . 75.69(6) ?
O5 V1 O4 . . 167.39(7) ?
N4 V1 O4 . . 73.68(7) ?
O3 V1 O4 . . 86.92(6) ?
O1 V1 O4 . . 83.33(6) ?
N1 V1 O4 . . 79.76(6) ?
C1 O1 V1 . . 119.51(13) ?
C10 O3 V1 . . 116.22(13) ?
C17 O4 V1 . . 112.25(13) ?
C24 O6 H6 . . 109.5 ?
C2 N1 N2 . . 122.37(17) ?
C2 N1 V1 . . 118.81(14) ?
N2 N1 V1 . . 118.25(13) ?
C10 N2 N1 . . 106.72(16) ?
C17 N3 N4 . . 114.23(16) ?
C17 N3 H3 . . 122.9 ?
N4 N3 H3 . . 122.9 ?
N3 N4 V1 . . 121.55(14) ?
N3 N4 H4 . . 119.2 ?
V1 N4 H4 . . 119.2 ?
O2 C1 O1 . . 124.82(19) ?
O2 C1 C2 . . 121.66(19) ?
O1 C1 C2 . . 113.50(18) ?
N1 C2 C3 . . 126.31(18) ?
N1 C2 C1 . . 111.75(18) ?
C3 C2 C1 . . 121.66(18) ?
C2 C3 C4 . . 108.71(16) ?
C2 C3 H3A . . 109.9 ?
C4 C3 H3A . . 109.9 ?
C2 C3 H3B . . 109.9 ?
C4 C3 H3B . . 109.9 ?
H3A C3 H3B . . 108.3 ?
C9 C4 C5 . . 118.9(2) ?
C9 C4 C3 . . 120.8(2) ?
C5 C4 C3 . . 120.2(2) ?
C6 C5 C4 . . 120.4(2) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C7 C6 C5 . . 120.1(2) ?
C7 C6 H6A . . 119.9 ?
C5 C6 H6A . . 119.9 ?
C8 C7 C6 . . 119.9(2) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C7 C8 C9 . . 120.1(2) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C8 C9 C4 . . 120.5(2) ?
C8 C9 H9 . . 119.7 ?
C4 C9 H9 . . 119.7 ?
O3 C10 N2 . . 123.85(18) ?
O3 C10 C11 . . 117.81(18) ?
N2 C10 C11 . . 118.34(18) ?
C16 C11 C12 . . 119.72(19) ?
C16 C11 C10 . . 120.61(19) ?
C12 C11 C10 . . 119.66(19) ?
C13 C12 C11 . . 120.1(2) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C14 C13 C12 . . 119.0(2) ?
C14 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
C13 C14 C15 . . 121.97(19) ?
C13 C14 Cl1 . . 119.34(17) ?
C15 C14 Cl1 . . 118.69(16) ?
C16 C15 C14 . . 118.7(2) ?
C16 C15 H15 . . 120.7 ?
C14 C15 H15 . . 120.7 ?
C15 C16 C11 . . 120.4(2) ?
C15 C16 H16 . . 119.8 ?
C11 C16 H16 . . 119.8 ?
O4 C17 N3 . . 117.01(19) ?
O4 C17 C18 . . 123.37(19) ?
N3 C17 C18 . . 119.62(18) ?
C19 C18 C23 . . 119.9(2) ?
C19 C18 C17 . . 117.78(19) ?
C23 C18 C17 . . 122.34(19) ?
C20 C19 C18 . . 120.3(2) ?
C20 C19 H19 . . 119.8 ?
C18 C19 H19 . . 119.8 ?
C19 C20 C21 . . 118.8(2) ?
C19 C20 H20 . . 120.6 ?
C21 C20 H20 . . 120.6 ?
C22 C21 C20 . . 121.8(2) ?
C22 C21 Cl2 . . 118.73(17) ?
C20 C21 Cl2 . . 119.44(17) ?
C21 C22 C23 . . 118.96(19) ?
C21 C22 H22 . . 120.5 ?
C23 C22 H22 . . 120.5 ?
C22 C23 C18 . . 120.22(19) ?
C22 C23 H23 . . 119.9 ?
C18 C23 H23 . . 119.9 ?
O6 C24 H24A . . 109.5 ?
O6 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
O6 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 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 O5 . 1.5905(15) ?
V1 N4 . 1.8797(17) ?
V1 O3 . 1.9697(15) ?
V1 O1 . 2.0036(15) ?
V1 N1 . 2.0791(17) ?
V1 O4 . 2.2149(15) ?
Cl1 C14 . 1.744(2) ?
Cl2 C21 . 1.736(2) ?
O1 C1 . 1.310(3) ?
O2 C1 . 1.217(3) ?
O3 C10 . 1.299(2) ?
O4 C17 . 1.248(2) ?
O6 C24 . 1.295(6) ?
O6 H6 . 0.8400 ?
N1 C2 . 1.284(3) ?
N1 N2 . 1.376(2) ?
N2 C10 . 1.318(3) ?
N3 C17 . 1.342(3) ?
N3 N4 . 1.359(2) ?
N3 H3 . 0.8800 ?
N4 H4 . 0.8800 ?
C1 C2 . 1.507(3) ?
C2 C3 . 1.493(3) ?
C3 C4 . 1.525(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C9 . 1.393(3) ?
C4 C5 . 1.395(3) ?
C5 C6 . 1.391(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.385(4) ?
C6 H6A . 0.9500 ?
C7 C8 . 1.385(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.389(4) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 C11 . 1.474(3) ?
C11 C16 . 1.395(3) ?
C11 C12 . 1.399(3) ?
C12 C13 . 1.387(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.379(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.392(3) ?
C15 C16 . 1.383(3) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 C18 . 1.478(3) ?
C18 C19 . 1.395(3) ?
C18 C23 . 1.395(3) ?
C19 C20 . 1.386(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.393(3) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.382(3) ?
C22 C23 . 1.389(3) ?
C22 H22 . 0.9500 ?
C23 H23 . 0.9500 ?
C24 H24A . 0.9800 ?
C24 H24B . 0.9800 ?
C24 H24C . 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
N3 H3 O1 2_666 0.88 1.98 2.741(2) 143 yes
N4 H4 O6 2_666 0.88 1.94 2.792(3) 162 yes
O6 H6 O2 . 0.84 2.27 2.908(3) 133 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
O5 V1 O1 C1 . . . . -118.37(15) ?
N4 V1 O1 C1 . . . . 147.00(15) ?
O3 V1 O1 C1 . . . . 2.2(2) ?
N1 V1 O1 C1 . . . . -6.82(14) ?
O4 V1 O1 C1 . . . . 74.27(14) ?
O5 V1 O3 C10 . . . . 105.44(15) ?
N4 V1 O3 C10 . . . . -158.01(14) ?
O1 V1 O3 C10 . . . . -15.2(2) ?
N1 V1 O3 C10 . . . . -6.14(14) ?
O4 V1 O3 C10 . . . . -86.36(14) ?
O5 V1 O4 C17 . . . . -8.3(4) ?
N4 V1 O4 C17 . . . . -9.75(14) ?
O3 V1 O4 C17 . . . . -120.08(14) ?
O1 V1 O4 C17 . . . . 88.58(14) ?
N1 V1 O4 C17 . . . . 165.18(15) ?
O5 V1 N1 C2 . . . . 100.74(16) ?
N4 V1 N1 C2 . . . . -67.0(2) ?
O3 V1 N1 C2 . . . . -167.36(16) ?
O1 V1 N1 C2 . . . . 7.94(15) ?
O4 V1 N1 C2 . . . . -77.72(15) ?
O5 V1 N1 N2 . . . . -87.67(15) ?
N4 V1 N1 N2 . . . . 104.63(19) ?
O3 V1 N1 N2 . . . . 4.23(13) ?
O1 V1 N1 N2 . . . . 179.52(14) ?
O4 V1 N1 N2 . . . . 93.86(14) ?
C2 N1 N2 C10 . . . . 169.75(18) ?
V1 N1 N2 C10 . . . . -1.5(2) ?
C17 N3 N4 V1 . . . . -8.5(2) ?
O5 V1 N4 N3 . . . . -170.15(15) ?
O3 V1 N4 N3 . . . . 90.49(15) ?
O1 V1 N4 N3 . . . . -71.68(15) ?
N1 V1 N4 N3 . . . . -1.5(3) ?
O4 V1 N4 N3 . . . . 9.53(14) ?
V1 O1 C1 O2 . . . . -173.47(16) ?
V1 O1 C1 C2 . . . . 5.1(2) ?
N2 N1 C2 C3 . . . . -4.7(3) ?
V1 N1 C2 C3 . . . . 166.52(16) ?
N2 N1 C2 C1 . . . . -178.68(16) ?
V1 N1 C2 C1 . . . . -7.5(2) ?
O2 C1 C2 N1 . . . . -179.70(19) ?
O1 C1 C2 N1 . . . . 1.7(2) ?
O2 C1 C2 C3 . . . . 6.0(3) ?
O1 C1 C2 C3 . . . . -172.65(18) ?
N1 C2 C3 C4 . . . . -93.3(2) ?
C1 C2 C3 C4 . . . . 80.1(2) ?
C2 C3 C4 C9 . . . . -93.2(2) ?
C2 C3 C4 C5 . . . . 83.8(2) ?
C9 C4 C5 C6 . . . . -1.2(3) ?
C3 C4 C5 C6 . . . . -178.3(2) ?
C4 C5 C6 C7 . . . . 0.0(4) ?
C5 C6 C7 C8 . . . . 0.9(4) ?
C6 C7 C8 C9 . . . . -0.6(4) ?
C7 C8 C9 C4 . . . . -0.5(4) ?
C5 C4 C9 C8 . . . . 1.4(3) ?
C3 C4 C9 C8 . . . . 178.5(2) ?
V1 O3 C10 N2 . . . . 8.3(3) ?
V1 O3 C10 C11 . . . . -171.56(13) ?
N1 N2 C10 O3 . . . . -4.2(3) ?
N1 N2 C10 C11 . . . . 175.61(16) ?
O3 C10 C11 C16 . . . . -168.54(18) ?
N2 C10 C11 C16 . . . . 11.6(3) ?
O3 C10 C11 C12 . . . . 12.4(3) ?
N2 C10 C11 C12 . . . . -167.50(19) ?
C16 C11 C12 C13 . . . . -0.3(3) ?
C10 C11 C12 C13 . . . . 178.82(18) ?
C11 C12 C13 C14 . . . . 0.9(3) ?
C12 C13 C14 C15 . . . . -0.5(3) ?
C12 C13 C14 Cl1 . . . . 179.08(16) ?
C13 C14 C15 C16 . . . . -0.6(3) ?
Cl1 C14 C15 C16 . . . . 179.84(16) ?
C14 C15 C16 C11 . . . . 1.2(3) ?
C12 C11 C16 C15 . . . . -0.8(3) ?
C10 C11 C16 C15 . . . . -179.91(18) ?
V1 O4 C17 N3 . . . . 8.5(2) ?
V1 O4 C17 C18 . . . . -170.65(15) ?
N4 N3 C17 O4 . . . . -1.4(3) ?
N4 N3 C17 C18 . . . . 177.84(17) ?
O4 C17 C18 C19 . . . . -4.5(3) ?
N3 C17 C18 C19 . . . . 176.35(19) ?
O4 C17 C18 C23 . . . . 174.85(19) ?
N3 C17 C18 C23 . . . . -4.3(3) ?
C23 C18 C19 C20 . . . . -1.3(3) ?
C17 C18 C19 C20 . . . . 178.0(2) ?
C18 C19 C20 C21 . . . . -0.3(4) ?
C19 C20 C21 C22 . . . . 1.6(4) ?
C19 C20 C21 Cl2 . . . . -177.59(19) ?
C20 C21 C22 C23 . . . . -1.2(3) ?
Cl2 C21 C22 C23 . . . . 178.00(15) ?
C21 C22 C23 C18 . . . . -0.5(3) ?
C19 C18 C23 C22 . . . . 1.8(3) ?
C17 C18 C23 C22 . . . . -177.57(18) ?
