#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:11:15 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179830 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/26/7012626.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_7012626
loop_
_publ_author_name
'Tolis, Evangelos J.'
'Manos, Manolis J.'
'Terzis, Aris'
'Raptopoulou, Catherine P.'
'Kabanos, Themistoklis A.'
_publ_section_title
;
 Mimicking the oxidized glutathione-VIVO2+ speciesAbbreviations used:
 bipy, 2,2'-bipyridine; phen, 1,10-phenanthroline; H3mpg,
 N-(2-mercaptopropionyl)glycine; H2mpgS--S2--, the oxidized-S,S dimer
 of H3mpg (see Scheme 1).
;
_journal_issue                   5
_journal_name_full               'Dalton Transactions'
_journal_page_first              775
_journal_paper_doi               10.1039/b212419j
_journal_year                    2003
_chemical_formula_sum            'C26 H26 N4 O9 V2'
_chemical_formula_weight         640.39
_chemical_name_systematic
;
?
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.38(1)
_cell_length_b                   8.235(4)
_cell_length_c                   16.64(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      11.7
_cell_measurement_theta_min      5.4
_cell_volume                     2793(3)
_computing_cell_refinement
'Program LEAST (UCLA Cryst.package, C.E.strouse 1994)'
_computing_data_collection
'Program COLLECT (UCLA Cryst.package, C.E.strouse 1994)'
_computing_data_reduction
'Program REDUCE (UCLA Cryst.package, C.E.strouse 1994)'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      298
_diffrn_measurement_device       'Crystal Logic Dual Goniometer'
_diffrn_measurement_method       'theta-2theta 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  0.1148
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4520
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        -2.4
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.728
_exptl_crystal_colour            orange-brown
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      1.50
_exptl_crystal_density_method    'floating method'
_exptl_crystal_description       parallelipiped
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.28(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.215
_refine_ls_goodness_of_fit_obs   1.191
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         4518
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.216
_refine_ls_restrained_S_obs      1.191
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_obs          0.0446
_refine_ls_shift/esd_max         -0.004
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0000P)²+2.4451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1095
_refine_ls_wR_factor_obs         0.1000
_reflns_number_observed          3982
_reflns_number_total             4519
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b212419j.txt
_cod_data_source_block           vobgsh
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'orthorhomibic' was replaced with
'orthorhombic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+2.4451P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+2.4451P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2794(1)
_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               7012626
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'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
V1 V 0.71726(4) 0.22713(9) -0.74033(5) 0.0436(2) Uani 1 d . .
V2 V 0.55189(4) 0.24032(10) -0.81817(5) 0.0441(2) Uani 1 d . .
O1 O 0.7559(2) 0.1447(4) -0.8129(2) 0.0548(9) Uani 1 d . .
O2 O 0.5098(2) 0.2460(5) -0.7387(3) 0.0663(10) Uani 1 d . .
O3 O 0.6390(2) 0.3217(5) -0.7880(2) 0.0497(9) Uani 1 d . .
O4 O 0.6640(2) 0.0293(4) -0.7056(2) 0.0527(9) Uani 1 d . .
O5 O 0.5853(2) 0.0088(4) -0.7987(2) 0.0553(10) Uani 1 d . .
O6 O 0.7613(2) 0.4478(4) -0.7385(2) 0.0538(9) Uani 1 d . .
O8 O 0.5379(2) 0.4574(5) -0.8680(2) 0.0523(9) Uani 1 d . .
N1 N 0.7922(2) 0.1553(5) -0.6557(3) 0.0458(10) Uani 1 d . .
N2 N 0.6854(2) 0.3115(5) -0.6161(3) 0.0509(11) Uani 1 d . .
N3 N 0.4718(2) 0.1504(5) -0.8918(3) 0.0472(10) Uani 1 d . .
N4 N 0.5924(2) 0.1707(6) -0.9441(3) 0.0500(11) Uani 1 d . .
C1 C 0.8471(3) 0.0790(7) -0.6800(4) 0.0512(14) Uani 1 d . .
C2 C 0.8945(3) 0.0271(8) -0.6285(4) 0.064(2) Uani 1 d . .
C3 C 0.8862(3) 0.0486(9) -0.5484(4) 0.069(2) Uani 1 d . .
C4 C 0.8310(3) 0.1291(9) -0.5211(4) 0.065(2) Uani 1 d . .
C5 C 0.7850(3) 0.1834(6) -0.5766(3) 0.0484(13) Uani 1 d . .
C6 C 0.7266(3) 0.2797(7) -0.5546(3) 0.0529(14) Uani 1 d . .
C7 C 0.7145(3) 0.3371(9) -0.4778(3) 0.065(2) Uani 1 d . .
C8 C 0.6612(4) 0.4306(9) -0.4650(4) 0.073(2) Uani 1 d . .
C9 C 0.6185(4) 0.4626(9) -0.5252(4) 0.070(2) Uani 1 d . .
C10 C 0.6319(4) 0.3988(8) -0.6017(4) 0.061(2) Uani 1 d . .
C11 C 0.4096(3) 0.1561(8) -0.8645(4) 0.062(2) Uani 1 d . .
C12 C 0.3571(4) 0.1144(10) -0.9122(5) 0.074(2) Uani 1 d . .
C13 C 0.3672(3) 0.0632(9) -0.9878(5) 0.076(2) Uani 1 d . .
C14 C 0.4301(3) 0.0519(8) -1.0155(4) 0.061(2) Uani 1 d . .
C15 C 0.4816(3) 0.0983(6) -0.9677(3) 0.0473(12) Uani 1 d . .
C16 C 0.5501(3) 0.0982(6) -0.9950(3) 0.0508(13) Uani 1 d . .
C17 C 0.5702(4) 0.0327(8) -1.0685(4) 0.065(2) Uani 1 d . .
C18 C 0.6354(4) 0.0464(10) -1.0887(5) 0.079(2) Uani 1 d . .
C19 C 0.6786(4) 0.1242(10) -1.0388(5) 0.079(2) Uani 1 d . .
C20 C 0.6547(3) 0.1819(9) -0.9663(4) 0.065(2) Uani 1 d . .
C21 C 0.6184(3) -0.0457(6) -0.7424(4) 0.0499(12) Uani 1 d . .
C22 C 0.6052(3) -0.2161(7) -0.7154(4) 0.064(2) Uani 1 d . .
H22A H 0.6301(16) -0.2386(18) -0.6678(15) 0.091(13) Uiso 1 calc R .
H22B H 0.6177(19) -0.2905(7) -0.7571(10) 0.091(13) Uiso 1 calc R .
H22C H 0.5592(5) -0.2283(15) -0.7041(24) 0.091(13) Uiso 1 calc R .
C23 C 0.7501(3) 0.5723(6) -0.7823(3) 0.0524(14) Uani 1 d . .
O7 O 0.7097(2) 0.5779(5) -0.8364(2) 0.0642(11) Uani 1 d . .
C24 C 0.7915(4) 0.7200(7) -0.7649(4) 0.080(2) Uani 1 d . .
H24A H 0.7976(17) 0.7304(30) -0.7079(4) 0.098(15) Uiso 1 calc R .
H24B H 0.7698(11) 0.8151(9) -0.7851(23) 0.098(15) Uiso 1 calc R .
H24C H 0.8334(9) 0.7086(24) -0.7905(21) 0.098(15) Uiso 1 calc R .
C25 C 0.4935(3) 0.5609(7) -0.8554(4) 0.0540(13) Uani 1 d . .
O9 O 0.4447(2) 0.5325(6) -0.8145(4) 0.097(2) Uani 1 d . .
C26 C 0.4999(4) 0.7207(7) -0.8950(5) 0.079(2) Uani 1 d . .
H26A H 0.5438(9) 0.7606(33) -0.8880(30) 0.137(21) Uiso 1 calc R .
H26B H 0.4694(20) 0.7956(20) -0.8715(24) 0.137(21) Uiso 1 calc R .
H26C H 0.4907(28) 0.7096(15) -0.9513(8) 0.137(21) Uiso 1 calc R .
HO3 H 0.6462(31) 0.4056(79) -0.8021(42) 0.071(22) Uiso 1 d . .
H1 H 0.8471(22) 0.0629(55) -0.7291(34) 0.037(13) Uiso 1 d . .
H2 H 0.9278(26) -0.0273(62) -0.6462(29) 0.037(14) Uiso 1 d . .
H3 H 0.9224(30) 0.0070(72) -0.5128(38) 0.070(18) Uiso 1 d . .
H4 H 0.8164(24) 0.1624(61) -0.4732(32) 0.041(14) Uiso 1 d . .
H7 H 0.7464(31) 0.3106(80) -0.4365(41) 0.074(19) Uiso 1 d . .
H8 H 0.6543(30) 0.4880(76) -0.4177(38) 0.066(19) Uiso 1 d . .
H9 H 0.5792(29) 0.5296(72) -0.5286(35) 0.059(17) Uiso 1 d . .
H10 H 0.6041(27) 0.4239(70) -0.6430(34) 0.054(17) Uiso 1 d . .
H11 H 0.4056(23) 0.1863(60) -0.8091(33) 0.042(13) Uiso 1 d . .
H12 H 0.3224(34) 0.1202(91) -0.9011(44) 0.080(25) Uiso 1 d . .
H13 H 0.3297(30) 0.0026(69) -1.0187(35) 0.060(16) Uiso 1 d . .
H14 H 0.4400(32) 0.0200(84) -1.0619(40) 0.075(24) Uiso 1 d . .
H17 H 0.5376(32) -0.0128(80) -1.1011(41) 0.072(21) Uiso 1 d . .
H18 H 0.6444(37) 0.0065(90) -1.1340(43) 0.086(24) Uiso 1 d . .
H19 H 0.7256(35) 0.1476(86) -1.0520(42) 0.087(22) Uiso 1 d . .
H20 H 0.6841(25) 0.2512(61) -0.9343(30) 0.042(14) Uiso 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'
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 V1 O3 105.4(2) . . ?
O1 V1 O6 100.1(2) . . ?
O3 V1 O6 90.6(2) . . ?
O1 V1 O4 97.9(2) . . ?
O3 V1 O4 89.9(2) . . ?
O6 V1 O4 161.2(2) . . ?
O1 V1 N1 91.6(2) . . ?
O3 V1 N1 162.9(2) . . ?
O6 V1 N1 85.5(2) . . ?
O4 V1 N1 88.5(2) . . ?
O1 V1 N2 163.7(2) . . ?
O3 V1 N2 90.8(2) . . ?
O6 V1 N2 80.7(2) . . ?
O4 V1 N2 80.5(2) . . ?
N1 V1 N2 72.1(2) . . ?
O2 V2 O3 105.6(2) . . ?
O2 V2 O8 104.1(2) . . ?
O3 V2 O8 86.0(2) . . ?
O2 V2 O5 94.3(2) . . ?
O3 V2 O5 88.7(2) . . ?
O8 V2 O5 161.5(2) . . ?
O2 V2 N3 94.2(2) . . ?
O3 V2 N3 160.2(2) . . ?
O8 V2 N3 87.9(2) . . ?
O5 V2 N3 91.2(2) . . ?
O2 V2 N4 163.1(2) . . ?
O3 V2 N4 89.6(2) . . ?
O8 V2 N4 84.1(2) . . ?
O5 V2 N4 78.2(2) . . ?
N3 V2 N4 71.0(2) . . ?
V1 O3 V2 135.2(2) . . ?
C21 O4 V1 129.8(3) . . ?
C21 O5 V2 129.6(3) . . ?
C23 O6 V1 129.2(3) . . ?
C25 O8 V2 129.9(4) . . ?
C5 N1 C1 117.7(5) . . ?
C5 N1 V1 120.9(4) . . ?
C1 N1 V1 121.3(4) . . ?
C10 N2 C6 118.6(5) . . ?
C10 N2 V1 124.3(4) . . ?
C6 N2 V1 116.9(4) . . ?
C11 N3 C15 117.7(5) . . ?
C11 N3 V2 120.4(4) . . ?
C15 N3 V2 121.8(4) . . ?
C20 N4 C16 117.8(5) . . ?
C20 N4 V2 125.1(4) . . ?
C16 N4 V2 116.7(3) . . ?
N1 C1 C2 123.2(6) . . ?
C3 C2 C1 119.3(7) . . ?
C2 C3 C4 119.2(6) . . ?
C3 C4 C5 119.0(6) . . ?
N1 C5 C4 121.4(6) . . ?
N1 C5 C6 115.0(5) . . ?
C4 C5 C6 123.5(5) . . ?
N2 C6 C7 121.5(6) . . ?
N2 C6 C5 114.7(5) . . ?
C7 C6 C5 123.8(5) . . ?
C8 C7 C6 119.0(7) . . ?
C7 C8 C9 120.8(7) . . ?
C8 C9 C10 118.2(7) . . ?
N2 C10 C9 121.7(7) . . ?
N3 C11 C12 122.0(7) . . ?
C13 C12 C11 119.9(7) . . ?
C12 C13 C14 118.8(7) . . ?
C13 C14 C15 120.2(7) . . ?
N3 C15 C14 121.3(6) . . ?
N3 C15 C16 115.4(5) . . ?
C14 C15 C16 123.2(5) . . ?
N4 C16 C17 122.3(6) . . ?
N4 C16 C15 114.4(5) . . ?
C17 C16 C15 123.2(6) . . ?
C18 C17 C16 117.7(7) . . ?
C19 C18 C17 120.7(7) . . ?
C18 C19 C20 117.6(7) . . ?
N4 C20 C19 123.8(7) . . ?
O5 C21 O4 125.8(5) . . ?
O5 C21 C22 117.9(5) . . ?
O4 C21 C22 116.3(5) . . ?
O7 C23 O6 124.8(5) . . ?
O7 C23 C24 119.2(5) . . ?
O6 C23 C24 116.0(5) . . ?
O9 C25 O8 123.0(5) . . ?
O9 C25 C26 119.2(6) . . ?
O8 C25 C26 117.7(6) . . ?
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
V1 O1 1.593(4) . ?
V1 O3 1.944(4) . ?
V1 O6 2.027(3) . ?
V1 O4 2.041(4) . ?
V1 N1 2.160(4) . ?
V1 N2 2.276(5) . ?
V2 O2 1.577(4) . ?
V2 O3 1.964(4) . ?
V2 O8 1.991(4) . ?
V2 O5 2.050(4) . ?
V2 N3 2.170(5) . ?
V2 N4 2.324(5) . ?
O4 C21 1.272(6) . ?
O5 C21 1.240(6) . ?
O6 C23 1.278(6) . ?
O8 C25 1.260(6) . ?
N1 C5 1.345(7) . ?
N1 C1 1.345(7) . ?
N2 C10 1.327(8) . ?
N2 C6 1.351(7) . ?
N3 C11 1.348(7) . ?
N3 C15 1.350(7) . ?
N4 C20 1.326(7) . ?
N4 C16 1.348(7) . ?
C1 C2 1.361(8) . ?
C2 C3 1.355(9) . ?
C3 C4 1.382(10) . ?
C4 C5 1.391(8) . ?
C5 C6 1.476(8) . ?
C6 C7 1.384(8) . ?
C7 C8 1.349(10) . ?
C8 C9 1.352(10) . ?
C9 C10 1.405(9) . ?
C11 C12 1.377(10) . ?
C12 C13 1.343(11) . ?
C13 C14 1.366(10) . ?
C14 C15 1.370(8) . ?
C15 C16 1.470(8) . ?
C16 C17 1.398(8) . ?
C17 C18 1.377(11) . ?
C18 C19 1.370(11) . ?
C19 C20 1.384(10) . ?
C21 C22 1.497(7) . ?
C23 O7 1.223(6) . ?
C23 C24 1.508(7) . ?
C25 O9 1.228(7) . ?
C25 C26 1.477(8) . ?
