#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:40:30 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301839 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/53/4335329.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_4335329
loop_
_publ_author_name
'Suman Kundu'
'Suvendu Maity'
'Thomas Weyhermüller'
'Prasanta Ghosh'
_publ_section_title
;
 Oxidovanadium Catechol Complexes: Radical versus Non-Radical States and
 Redox Series
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7417
_journal_page_last               7430
_journal_paper_doi               10.1021/ic400166z
_journal_volume                  52
_journal_year                    2013
_chemical_compound_source        'dichloromethane, pentane'
_chemical_formula_moiety         'C26 H30 N3 O4 V'
_chemical_formula_sum            'C26 H30 N3 O4 V'
_chemical_formula_weight         499.47
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                WGT-PG-500-10
_audit_creation_date             2011-02-18
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.545(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9332(8)
_cell_length_b                   9.8988(5)
_cell_length_c                   18.1730(6)
_cell_measurement_reflns_used    76065
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.0996
_cell_measurement_theta_min      2.6966
_cell_volume                     2490.1(2)
_computing_cell_refinement       'DENZO (Bruker AXS, 2006)'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'DENZO (Bruker AXS, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            69606
_diffrn_reflns_theta_full        33.16
_diffrn_reflns_theta_max         33.16
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_T_max  0.94061
_exptl_absorpt_correction_T_min  0.91270
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         9492
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0387
_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)+(0.0336P)²+1.6444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                7940
_reflns_number_total             9492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic400166z_si_003_2.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4335329
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
V1 V 0.944885(14) 0.65198(2) 0.150037(11) 0.01387(5) Uani 1 1 d .
O40 O 0.97775(7) 0.79128(10) 0.19058(5) 0.02080(18) Uani 1 1 d .
O1 O 1.01306(7) 0.52342(10) 0.21467(5) 0.02099(18) Uani 1 1 d .
C2 C 1.10445(9) 0.48603(13) 0.22692(7) 0.0186(2) Uani 1 1 d .
C3 C 1.13802(10) 0.42096(14) 0.29401(8) 0.0235(3) Uani 1 1 d .
H3 H 1.0958 0.4101 0.3311 0.028 Uiso 1 1 calc R
C4 C 1.23155(11) 0.37276(15) 0.30654(9) 0.0288(3) Uani 1 1 d .
H4 H 1.2524 0.3285 0.3519 0.035 Uiso 1 1 calc R
C5 C 1.29609(11) 0.38802(18) 0.25351(10) 0.0329(3) Uani 1 1 d .
H5 H 1.3603 0.3549 0.2627 0.040 Uiso 1 1 calc R
C6 C 1.26499(10) 0.45201(16) 0.18750(9) 0.0288(3) Uani 1 1 d .
H6 H 1.3084 0.4624 0.1512 0.035 Uiso 1 1 calc R
C7 C 1.16968(9) 0.50232(14) 0.17295(8) 0.0206(2) Uani 1 1 d .
C8 C 1.14046(9) 0.56154(13) 0.10189(8) 0.0200(2) Uani 1 1 d .
H8 H 1.1847 0.5583 0.0659 0.024 Uiso 1 1 calc R
N9 N 1.05735(7) 0.61941(11) 0.08350(6) 0.01637(18) Uani 1 1 d .
N10 N 1.04066(8) 0.66737(12) 0.01161(6) 0.0196(2) Uani 1 1 d D
H10 H 1.0715(12) 0.6249(17) -0.0218(8) 0.024 Uiso 1 1 d D
C11 C 0.95383(9) 0.72906(13) -0.00701(7) 0.0180(2) Uani 1 1 d .
C12 C 0.92794(11) 0.77677(15) -0.07942(8) 0.0251(3) Uani 1 1 d .
H12 H 0.9703 0.7660 -0.1164 0.030 Uiso 1 1 calc R
C13 C 0.84007(12) 0.83918(17) -0.09548(8) 0.0298(3) Uani 1 1 d .
H13 H 0.8205 0.8715 -0.1441 0.036 Uiso 1 1 calc R
C14 C 0.77920(12) 0.85489(17) -0.03930(9) 0.0300(3) Uani 1 1 d .
H14 H 0.7185 0.8988 -0.0493 0.036 Uiso 1 1 calc R
C15 C 0.80937(10) 0.80546(15) 0.03033(8) 0.0233(2) Uani 1 1 d .
H15 H 0.7684 0.8162 0.0683 0.028 Uiso 1 1 calc R
N16 N 0.89553(8) 0.74184(11) 0.04681(6) 0.01712(19) Uani 1 1 d .
O21 O 0.82098(6) 0.64428(9) 0.18080(5) 0.01482(15) Uani 1 1 d .
C22 C 0.75507(8) 0.55528(12) 0.15285(6) 0.01324(19) Uani 1 1 d .
C23 C 0.65857(8) 0.55015(12) 0.17121(6) 0.01345(19) Uani 1 1 d .
C24 C 0.60139(8) 0.44710(12) 0.13844(7) 0.0152(2) Uani 1 1 d .
H24 H 0.5369 0.4397 0.1503 0.018 Uiso 1 1 calc R
C25 C 0.63355(9) 0.35190(12) 0.08819(6) 0.0155(2) Uani 1 1 d .
C26 C 0.72706(9) 0.36143(12) 0.06931(7) 0.0154(2) Uani 1 1 d .
H26 H 0.7490 0.3004 0.0345 0.019 Uiso 1 1 calc R
C27 C 0.78906(8) 0.46201(12) 0.10210(6) 0.01392(19) Uani 1 1 d .
O28 O 0.88007(6) 0.47761(9) 0.09032(5) 0.01695(16) Uani 1 1 d .
C29 C 0.62169(8) 0.64930(12) 0.22624(7) 0.0160(2) Uani 1 1 d .
C30 C 0.51236(9) 0.63323(14) 0.22937(8) 0.0202(2) Uani 1 1 d .
H30A H 0.4781 0.6446 0.1796 0.030 Uiso 1 1 calc R
H30B H 0.4902 0.7018 0.2625 0.030 Uiso 1 1 calc R
H30C H 0.4991 0.5431 0.2480 0.030 Uiso 1 1 calc R
C31 C 0.64079(10) 0.79661(14) 0.20425(9) 0.0244(3) Uani 1 1 d .
H31A H 0.7106 0.8122 0.2073 0.037 Uiso 1 1 calc R
H31B H 0.6126 0.8583 0.2381 0.037 Uiso 1 1 calc R
H31C H 0.6113 0.8129 0.1534 0.037 Uiso 1 1 calc R
C32 C 0.67342(10) 0.61934(16) 0.30411(7) 0.0249(3) Uani 1 1 d .
H32A H 0.6596 0.5263 0.3181 0.037 Uiso 1 1 calc R
H32B H 0.6503 0.6820 0.3399 0.037 Uiso 1 1 calc R
H32C H 0.7432 0.6307 0.3038 0.037 Uiso 1 1 calc R
C33 C 0.56371(10) 0.24108(14) 0.05719(7) 0.0202(2) Uani 1 1 d .
C34 C 0.52770(12) 0.16196(15) 0.12151(8) 0.0274(3) Uani 1 1 d .
H34A H 0.4945 0.2237 0.1523 0.041 Uiso 1 1 calc R
H34B H 0.5828 0.1206 0.1515 0.041 Uiso 1 1 calc R
H34C H 0.4828 0.0912 0.1016 0.041 Uiso 1 1 calc R
C35 C 0.47666(13) 0.3059(2) 0.01091(10) 0.0398(4) Uani 1 1 d .
H35A H 0.4990 0.3582 -0.0296 0.060 Uiso 1 1 calc R
H35B H 0.4430 0.3658 0.0424 0.060 Uiso 1 1 calc R
H35C H 0.4323 0.2350 -0.0096 0.060 Uiso 1 1 calc R
C36 C 0.61247(15) 0.1417(2) 0.00878(12) 0.0479(6) Uani 1 1 d .
H36A H 0.5670 0.0696 -0.0080 0.072 Uiso 1 1 calc R
H36B H 0.6694 0.1024 0.0376 0.072 Uiso 1 1 calc R
H36C H 0.6323 0.1894 -0.0343 0.072 Uiso 1 1 calc R
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 -1.00 0.1100
1.00 0.00 1.00 0.1100
-1.00 0.00 2.00 0.1100
1.00 0.00 -2.00 0.1100
0.00 1.00 0.00 0.0800
1.00 -2.00 -2.00 0.0700
1.00 1.00 -2.00 0.1000
-1.00 -2.00 2.00 0.1300
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O40 V1 O21 97.02(4)
O40 V1 O1 101.20(5)
O21 V1 O1 101.52(4)
O40 V1 N9 101.69(5)
O21 V1 N9 158.95(4)
O1 V1 N9 84.31(4)
O40 V1 N16 95.31(5)
O21 V1 N16 93.67(4)
O1 V1 N16 155.90(4)
N9 V1 N16 75.17(4)
O40 V1 O28 171.58(4)
O21 V1 O28 76.88(3)
O1 V1 O28 85.84(4)
N9 V1 O28 83.47(4)
N16 V1 O28 79.47(4)
C2 O1 V1 133.87(9)
O1 C2 C3 119.47(12)
O1 C2 C7 122.18(12)
C3 C2 C7 118.26(12)
C4 C3 C2 120.89(14)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 121.15(14)
C3 C4 H4 119.4
C5 C4 H4 119.4
C6 C5 C4 119.00(14)
C6 C5 H5 120.5
C4 C5 H5 120.5
C5 C6 C7 121.23(14)
C5 C6 H6 119.4
C7 C6 H6 119.4
C6 C7 C2 119.46(13)
C6 C7 C8 118.44(13)
C2 C7 C8 122.00(11)
N9 C8 C7 124.34(12)
N9 C8 H8 117.8
C7 C8 H8 117.8
C8 N9 N10 116.24(11)
C8 N9 V1 128.13(9)
N10 N9 V1 115.62(8)
C11 N10 N9 115.90(10)
C11 N10 H10 121.8(12)
N9 N10 H10 116.2(12)
N16 C11 N10 116.98(11)
N16 C11 C12 122.45(12)
N10 C11 C12 120.58(11)
C13 C12 C11 118.53(13)
C13 C12 H12 120.7
C11 C12 H12 120.7
C12 C13 C14 119.46(14)
C12 C13 H13 120.3
C14 C13 H13 120.3
C15 C14 C13 118.75(13)
C15 C14 H14 120.6
C13 C14 H14 120.6
N16 C15 C14 122.47(13)
N16 C15 H15 118.8
C14 C15 H15 118.8
C11 N16 C15 118.33(11)
C11 N16 V1 116.22(8)
C15 N16 V1 125.40(9)
C22 O21 V1 122.11(7)
O21 C22 C23 124.31(10)
O21 C22 C27 114.23(10)
C23 C22 C27 121.46(10)
C24 C23 C22 115.96(10)
C24 C23 C29 122.21(10)
C22 C23 C29 121.79(10)
C23 C24 C25 123.82(10)
C23 C24 H24 118.1
C25 C24 H24 118.1
C26 C25 C24 119.20(11)
C26 C25 C33 122.22(11)
C24 C25 C33 118.58(10)
C25 C26 C27 119.49(10)
C25 C26 H26 120.3
C27 C26 H26 120.3
O28 C27 C26 124.74(10)
O28 C27 C22 115.24(10)
C26 C27 C22 120.02(10)
C27 O28 V1 111.31(7)
C23 C29 C30 111.42(10)
C23 C29 C32 108.63(10)
C30 C29 C32 107.89(10)
C23 C29 C31 110.85(10)
C30 C29 C31 107.94(10)
C32 C29 C31 110.06(11)
C29 C30 H30A 109.5
C29 C30 H30B 109.5
H30A C30 H30B 109.5
C29 C30 H30C 109.5
H30A C30 H30C 109.5
H30B C30 H30C 109.5
C29 C31 H31A 109.5
C29 C31 H31B 109.5
H31A C31 H31B 109.5
C29 C31 H31C 109.5
H31A C31 H31C 109.5
H31B C31 H31C 109.5
C29 C32 H32A 109.5
C29 C32 H32B 109.5
H32A C32 H32B 109.5
C29 C32 H32C 109.5
H32A C32 H32C 109.5
H32B C32 H32C 109.5
C36 C33 C25 111.55(11)
C36 C33 C35 109.18(15)
C25 C33 C35 109.37(12)
C36 C33 C34 108.32(14)
C25 C33 C34 109.52(10)
C35 C33 C34 108.86(13)
C33 C34 H34A 109.5
C33 C34 H34B 109.5
H34A C34 H34B 109.5
C33 C34 H34C 109.5
H34A C34 H34C 109.5
H34B C34 H34C 109.5
C33 C35 H35A 109.5
C33 C35 H35B 109.5
H35A C35 H35B 109.5
C33 C35 H35C 109.5
H35A C35 H35C 109.5
H35B C35 H35C 109.5
C33 C36 H36A 109.5
C33 C36 H36B 109.5
H36A C36 H36B 109.5
C33 C36 H36C 109.5
H36A C36 H36C 109.5
H36B C36 H36C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
V1 O40 1.6053(10)
V1 O21 1.8758(8)
V1 O1 1.9097(10)
V1 N9 2.1103(10)
V1 N16 2.1188(11)
V1 O28 2.1793(9)
O1 C2 1.3205(15)
C2 C3 1.4108(19)
C2 C7 1.4202(19)
C3 C4 1.382(2)
C3 H3 0.9500
C4 C5 1.399(2)
C4 H4 0.9500
C5 C6 1.382(2)
C5 H5 0.9500
C6 C7 1.4147(18)
C6 H6 0.9500
C7 C8 1.4343(19)
C8 N9 1.3010(16)
C8 H8 0.9500
N9 N10 1.3846(15)
N10 C11 1.3629(16)
N10 H10 0.889(9)
C11 N16 1.3467(16)
C11 C12 1.4059(19)
C12 C13 1.373(2)
C12 H12 0.9500
C13 C14 1.408(2)
C13 H13 0.9500
C14 C15 1.377(2)
C14 H14 0.9500
C15 N16 1.3584(17)
C15 H15 0.9500
O21 C22 1.3309(14)
C22 C23 1.4226(15)
C22 C27 1.4236(16)
C23 C24 1.3862(16)
C23 C29 1.5313(16)
C24 C25 1.4199(16)
C24 H24 0.9500
C25 C26 1.3878(16)
C25 C33 1.5305(17)
C26 C27 1.4055(16)
C26 H26 0.9500
C27 O28 1.3188(14)
C29 C30 1.5390(17)
C29 C32 1.5419(19)
C29 C31 1.5430(19)
C30 H30A 0.9800
C30 H30B 0.9800
C30 H30C 0.9800
C31 H31A 0.9800
C31 H31B 0.9800
C31 H31C 0.9800
C32 H32A 0.9800
C32 H32B 0.9800
C32 H32C 0.9800
C33 C36 1.530(2)
C33 C35 1.535(2)
C33 C34 1.5379(19)
C34 H34A 0.9800
C34 H34B 0.9800
C34 H34C 0.9800
C35 H35A 0.9800
C35 H35B 0.9800
C35 H35C 0.9800
C36 H36A 0.9800
C36 H36B 0.9800
C36 H36C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N10 H10 O28 0.889(9) 1.796(9) 2.6790(14) 171.9(18) 3_765
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139139814
