#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:13:32 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179051 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/13/4301355.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_4301355
loop_
_publ_author_name
'Pabitra Baran Chatterjee'
'Kisholoy Bhattacharya'
'Nabanita Kundu'
'Ki-Young Choi'
'Rodolphe Clérac'
'Muktimoy Chaudhury'
_publ_section_title
;
Vanadium-Induced Nucleophilic IPSO Substitutions in a Coordinated
Tetrachlorosemiquinone Ring: Formation of the Chloranilate Anion as a
Bridging Ligand
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              804
_journal_page_last               806
_journal_paper_doi               10.1021/ic801985g
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C26 H16 Cl4 N4 O6 V2'
_chemical_formula_weight         724.11
_chemical_name_systematic
;
 ?
;
_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                98.602(6)
_cell_angle_beta                 95.049(6)
_cell_angle_gamma                105.828(6)
_cell_formula_units_Z            1
_cell_length_a                   6.873(2)
_cell_length_b                   8.512(3)
_cell_length_c                   13.076(4)
_cell_measurement_reflns_used    2438
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      27.3815
_cell_measurement_theta_min      2.529
_cell_volume                     721.0(4)
_computing_cell_refinement       'SMART (Brucker, 1999)'
_computing_data_collection       'SMART (Brucker, 1999)'
_computing_data_reduction        'SAINT-plus (bruker, 1999)'
_computing_molecular_graphics    'Ortep-3 for windows(Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldric, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL97 (Sheldric, 1997)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD dffractometer'
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9818
_diffrn_reflns_theta_full        28.47
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         2.53
_diffrn_standards_decay_%        -0.0002
_exptl_absorpt_coefficient_mu    1.067
_exptl_absorpt_correction_T_max  0.9633
_exptl_absorpt_correction_T_min  0.8511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0446
_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)+(0.0648P)²+0.2566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                2463
_reflns_number_total             3620
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801985g_si_003.cif
_cod_data_source_block           2
_cod_original_cell_volume        720.9(4)
_cod_database_code               4301355
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
V V 0.49821(8) 0.05132(6) 0.69496(4) 0.02864(16) Uani 1 1 d . . .
Cl1 Cl 0.15529(13) -0.10017(10) 0.67831(7) 0.0468(2) Uani 1 1 d . . .
Cl2 Cl 0.34157(15) 0.31420(10) 1.06105(6) 0.0462(2) Uani 1 1 d . . .
O1 O 0.5774(4) -0.0434(3) 0.60097(16) 0.0403(5) Uani 1 1 d . . .
O2 O 0.5779(3) -0.0772(2) 0.80310(15) 0.0321(5) Uani 1 1 d . . .
O3 O 0.4412(3) 0.1746(2) 0.85220(15) 0.0313(5) Uani 1 1 d . . .
N1 N 0.4194(4) 0.2494(3) 0.63745(18) 0.0269(5) Uani 1 1 d . . .
N2 N 0.7647(4) 0.2532(3) 0.74231(18) 0.0287(5) Uani 1 1 d . . .
C1 C 0.2453(5) 0.2366(4) 0.5772(2) 0.0340(7) Uani 1 1 d . . .
H1 H 0.1537 0.1306 0.5521 0.041 Uiso 1 1 calc R . .
C2 C 0.1957(5) 0.3732(4) 0.5507(2) 0.0382(7) Uani 1 1 d . . .
H2 H 0.0738 0.3599 0.5071 0.046 Uiso 1 1 calc R . .
C3 C 0.3275(5) 0.5301(4) 0.5890(2) 0.0374(7) Uani 1 1 d . . .
H3 H 0.2948 0.6251 0.5738 0.045 Uiso 1 1 calc R . .
C4 C 0.5079(5) 0.5440(4) 0.6498(2) 0.0320(7) Uani 1 1 d . . .
H4 H 0.5998 0.6493 0.6767 0.038 Uiso 1 1 calc R . .
C5 C 0.5531(4) 0.4024(3) 0.6712(2) 0.0253(6) Uani 1 1 d . . .
C6 C 0.7484(4) 0.4034(3) 0.7273(2) 0.0268(6) Uani 1 1 d . . .
C7 C 0.9099(5) 0.5454(4) 0.7601(2) 0.0349(7) Uani 1 1 d . . .
H7 H 0.8967 0.6492 0.7498 0.042 Uiso 1 1 calc R . .
C8 C 1.0911(5) 0.5336(4) 0.8084(3) 0.0416(8) Uani 1 1 d . . .
H8 H 1.2019 0.6293 0.8320 0.050 Uiso 1 1 calc R . .
C9 C 1.1077(5) 0.3802(5) 0.8217(3) 0.0424(8) Uani 1 1 d . . .
H9 H 1.2306 0.3696 0.8533 0.051 Uiso 1 1 calc R . .
C10 C 0.9424(5) 0.2428(4) 0.7881(2) 0.0371(7) Uani 1 1 d . . .
H10 H 0.9539 0.1382 0.7975 0.045 Uiso 1 1 calc R . .
C11 C 0.5429(4) -0.0497(3) 0.8969(2) 0.0264(6) Uani 1 1 d . . .
C12 C 0.4651(4) 0.1004(3) 0.9258(2) 0.0260(6) Uani 1 1 d . . .
C13 C 0.4264(5) 0.1426(3) 1.0283(2) 0.0286(6) Uani 1 1 d . . .
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 V O2 95.59(10) . . ?
O1 V N2 97.59(11) . . ?
O2 V N2 93.08(9) . . ?
O1 V N1 105.53(10) . . ?
O2 V N1 157.45(8) . . ?
N2 V N1 76.60(9) . . ?
O1 V O3 167.14(10) . . ?
O2 V O3 73.30(8) . . ?
N2 V O3 77.02(8) . . ?
N1 V O3 84.77(8) . . ?
O1 V Cl1 102.65(9) . . ?
O2 V Cl1 91.90(7) . . ?
N2 V Cl1 158.56(7) . . ?
N1 V Cl1 91.12(7) . . ?
O3 V Cl1 84.50(6) . . ?
C11 O2 V 121.75(18) . . ?
C12 O3 V 114.52(17) . . ?
C1 N1 C5 118.4(2) . . ?
C1 N1 V 125.68(19) . . ?
C5 N1 V 115.81(18) . . ?
C10 N2 C6 119.1(3) . . ?
C10 N2 V 124.8(2) . . ?
C6 N2 V 116.01(19) . . ?
N1 C1 C2 122.5(3) . . ?
C1 C2 C3 119.2(3) . . ?
C4 C3 C2 118.6(3) . . ?
C3 C4 C5 119.8(3) . . ?
N1 C5 C4 121.4(3) . . ?
N1 C5 C6 114.8(2) . . ?
C4 C5 C6 123.8(3) . . ?
N2 C6 C7 121.0(3) . . ?
N2 C6 C5 115.6(2) . . ?
C7 C6 C5 123.3(3) . . ?
C6 C7 C8 119.3(3) . . ?
C9 C8 C7 119.3(3) . . ?
C10 C9 C8 119.1(3) . . ?
N2 C10 C9 122.1(3) . . ?
O2 C11 C13 125.0(2) . 2_657 ?
O2 C11 C12 115.3(2) . . ?
C13 C11 C12 119.7(2) 2_657 . ?
O3 C12 C13 126.2(2) . . ?
O3 C12 C11 114.5(2) . . ?
C13 C12 C11 119.3(2) . . ?
C11 C13 C12 120.9(2) 2_657 . ?
C11 C13 Cl2 119.9(2) 2_657 . ?
C12 C13 Cl2 119.2(2) . . ?
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
V V 5.0459(19) 2_656 ?
V V 9.996(4) 2_646 ?
V O1 1.586(2) . ?
V O2 2.037(2) . ?
V N2 2.111(3) . ?
V N1 2.123(2) . ?
V O3 2.281(2) . ?
V Cl1 2.3308(12) . ?
Cl2 C13 1.726(3) . ?
O2 C11 1.270(3) . ?
O3 C12 1.250(3) . ?
N1 C1 1.342(4) . ?
N1 C5 1.356(4) . ?
N2 C10 1.343(4) . ?
N2 C6 1.355(3) . ?
C1 C2 1.380(4) . ?
C2 C3 1.383(5) . ?
C3 C4 1.379(4) . ?
C4 C5 1.385(4) . ?
C5 C6 1.469(4) . ?
C6 C7 1.381(4) . ?
C7 C8 1.382(5) . ?
C8 C9 1.376(5) . ?
C9 C10 1.373(5) . ?
C11 C13 1.383(4) 2_657 ?
C11 C12 1.524(4) . ?
C12 C13 1.403(4) . ?
C13 C11 1.383(4) 2_657 ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 V O2 C11 -178.9(2) . . . . ?
N2 V O2 C11 83.1(2) . . . . ?
N1 V O2 C11 21.5(4) . . . . ?
O3 V O2 C11 7.7(2) . . . . ?
Cl1 V O2 C11 -76.0(2) . . . . ?
O1 V O3 C12 -37.2(5) . . . . ?
O2 V O3 C12 -6.27(19) . . . . ?
N2 V O3 C12 -103.6(2) . . . . ?
N1 V O3 C12 179.0(2) . . . . ?
Cl1 V O3 C12 87.4(2) . . . . ?
O1 V N1 C1 80.2(3) . . . . ?
O2 V N1 C1 -120.9(3) . . . . ?
N2 V N1 C1 174.5(2) . . . . ?
O3 V N1 C1 -107.6(2) . . . . ?
Cl1 V N1 C1 -23.3(2) . . . . ?
O1 V N1 C5 -104.3(2) . . . . ?
O2 V N1 C5 54.5(3) . . . . ?
N2 V N1 C5 -10.02(18) . . . . ?
O3 V N1 C5 67.85(19) . . . . ?
Cl1 V N1 C5 152.22(18) . . . . ?
O1 V N2 C10 -69.7(2) . . . . ?
O2 V N2 C10 26.4(2) . . . . ?
N1 V N2 C10 -173.9(2) . . . . ?
O3 V N2 C10 98.4(2) . . . . ?
Cl1 V N2 C10 129.5(2) . . . . ?
O1 V N2 C6 112.5(2) . . . . ?
O2 V N2 C6 -151.48(19) . . . . ?
N1 V N2 C6 8.23(19) . . . . ?
O3 V N2 C6 -79.40(19) . . . . ?
Cl1 V N2 C6 -48.3(3) . . . . ?
C5 N1 C1 C2 -1.6(4) . . . . ?
V N1 C1 C2 173.8(2) . . . . ?
N1 C1 C2 C3 -1.3(5) . . . . ?
C1 C2 C3 C4 2.1(5) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C1 N1 C5 C4 3.8(4) . . . . ?
V N1 C5 C4 -172.0(2) . . . . ?
C1 N1 C5 C6 -173.9(2) . . . . ?
V N1 C5 C6 10.3(3) . . . . ?
C3 C4 C5 N1 -3.0(4) . . . . ?
C3 C4 C5 C6 174.5(3) . . . . ?
C10 N2 C6 C7 -1.3(4) . . . . ?
V N2 C6 C7 176.7(2) . . . . ?
C10 N2 C6 C5 176.5(2) . . . . ?
V N2 C6 C5 -5.5(3) . . . . ?
N1 C5 C6 N2 -3.2(3) . . . . ?
C4 C5 C6 N2 179.2(3) . . . . ?
N1 C5 C6 C7 174.6(3) . . . . ?
C4 C5 C6 C7 -3.1(4) . . . . ?
N2 C6 C7 C8 0.4(4) . . . . ?
C5 C6 C7 C8 -177.2(3) . . . . ?
C6 C7 C8 C9 0.8(5) . . . . ?
C7 C8 C9 C10 -1.1(5) . . . . ?
C6 N2 C10 C9 1.0(4) . . . . ?
V N2 C10 C9 -176.8(2) . . . . ?
C8 C9 C10 N2 0.2(5) . . . . ?
V O2 C11 C13 173.2(2) . . . 2_657 ?
V O2 C11 C12 -8.0(3) . . . . ?
V O3 C12 C13 -175.3(2) . . . . ?
V O3 C12 C11 4.4(3) . . . . ?
O2 C11 C12 O3 1.7(4) . . . . ?
C13 C11 C12 O3 -179.4(3) 2_657 . . . ?
O2 C11 C12 C13 -178.7(3) . . . . ?
C13 C11 C12 C13 0.2(5) 2_657 . . . ?
O3 C12 C13 C11 179.4(3) . . . 2_657 ?
C11 C12 C13 C11 -0.2(5) . . . 2_657 ?
O3 C12 C13 Cl2 -1.2(4) . . . . ?
C11 C12 C13 Cl2 179.1(2) . . . . ?
