# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1898796'
loop_
_audit_author_name
_audit_author_address
'Antonios HATZIDIMITRIOU'
;Aristotle University of Thessaloniki
Greece
;
_audit_update_record             
;
2019-02-22 deposited with the CCDC.	2019-10-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_1                   
;
PROBLEM: Short Inter D...A Contact  O1       ..N2       .       2.85 Ang.
RESPONSE: There is no hydrogen bonding interaction between the atoms. They are just close as they participate the coordination sphere around the metal ion.
;
_vrf_PLAT430_1_2                 
;
PROBLEM: Short Inter D...A Contact  O2       ..N2       .       2.76 Ang.
RESPONSE: There is no hydrogen bonding interaction between the atoms. They are just close as they participate the coordination sphere around the metal ion.
;
_vrf_PLAT430_1_3                 
;
PROBLEM: Short Inter D...A Contact  O5       ..N2       .       2.80 Ang.
RESPONSE: There is no hydrogen bonding interaction between the atoms. They are just close as they participate the coordination sphere around the metal ion.
;
# Added during the CSD deposition process: Friday 22 February 2019 08:36 AM
# end Validation Reply Form


_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.9698(8)
_cell_length_b                   10.5539(11)
_cell_length_c                   11.3860(12)
_cell_angle_alpha                98.204(3)
_cell_angle_beta                 99.184(3)
_cell_angle_gamma                90.805(4)
_cell_volume                     935.09(10)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
V 0.3005 0.5294 10.2971 6.8657 7.3511 0.4385 2.0703 26.8938 2.0571 102.4780
1.2199 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C21 H18 N4 O2 V1 
# Dc =      1.45 Fooo =    430.00 Mu =      5.55 M =    409.34
# Found Formula = C20 H18 N2 O5 V1 
# Dc =      1.48 FOOO =    430.00 Mu =      5.65 M =    417.31

_chemical_formula_sum            'C20 H18 N2 O5 V1'
_chemical_formula_moiety         'C20 H18 N2 O5 V1'
_chemical_compound_source        ?
_chemical_formula_weight         417.31


_cell_measurement_reflns_used    296
_cell_measurement_theta_min      10
_cell_measurement_theta_max      20
_cell_measurement_temperature    295

_exptl_crystal_description       bar
_exptl_crystal_colour            brown
_exptl_crystal_size_min          0.140
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_max          0.390

_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             430
_exptl_absorpt_coefficient_mu    0.565

# Sheldrick geometric approximatio 0.91 0.92 
# No experimental values of Tmin/max available 
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.92
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      295
_diffrn_reflns_number            11781
_reflns_number_total             7021
_diffrn_reflns_av_R_equivalents  0.025
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 7021 
# Theoretical number of reflections is about 14304 


_diffrn_reflns_theta_min         1.951
_diffrn_reflns_theta_max         33.178
_diffrn_measured_fraction_theta_max 0.979

_diffrn_reflns_theta_full        25.215
_diffrn_measured_fraction_theta_full 0.990


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -16
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   1.82
_oxford_diffrn_Wilson_scale      30.73

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.38
_refine_diff_density_max         0.60


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         3498
_refine_ls_number_restraints     0
_refine_ls_number_parameters     253
_oxford_refine_ls_R_factor_ref   0.0443
_refine_ls_wR_factor_ref         0.1056
_refine_ls_goodness_of_fit_ref   0.9995
_refine_ls_shift/su_max          0.0008163
_refine_ls_shift/su_mean         0.0000417


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4208
_refine_ls_R_factor_all          0.0549
_refine_ls_wR_factor_all         0.1113

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3498
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_gt          0.1056

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 8.73 14.4 8.77 3.82 0.921 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
V1 V 0.53118(4) 0.70181(3) 0.83406(3) 0.0271 1.0000 Uani . . . . . .
O1 O 0.3915(2) 0.73657(17) 0.69087(15) 0.0363 1.0000 Uani . . . . . .
O2 O 0.7403(2) 0.71416(15) 0.93519(14) 0.0329 1.0000 Uani . . . . . .
O3 O 0.4078(2) 0.72982(16) 0.93165(16) 0.0382 1.0000 Uani . . . . . .
O4 O 0.9808(3) 0.64385(19) 1.0929(2) 0.0547 1.0000 Uani . . . . . .
O5 O 0.4979(2) 0.53336(15) 0.79436(16) 0.0376 1.0000 Uani . . . . . .
N1 N 0.5799(2) 0.90430(18) 0.83756(16) 0.0286 1.0000 Uani . . . . . .
N2 N 0.7332(2) 0.6613(2) 0.68979(18) 0.0365 1.0000 Uani . . . . . .
C1 C 0.3799(3) 0.8548(2) 0.6637(2) 0.0358 1.0000 Uani . . . . . .
C2 C 0.2711(4) 0.8843(3) 0.5630(2) 0.0535 1.0000 Uani . . . . . .
C3 C 0.2658(5) 1.0096(4) 0.5417(3) 0.0699 1.0000 Uani . . . . . .
C4 C 0.3661(5) 1.1052(4) 0.6170(3) 0.0699 1.0000 Uani . . . . . .
C5 C 0.4743(4) 1.0773(3) 0.7173(3) 0.0514 1.0000 Uani . . . . . .
C6 C 0.4810(3) 0.9522(2) 0.7399(2) 0.0346 1.0000 Uani . . . . . .
C7 C 0.6655(3) 0.9785(2) 0.9269(2) 0.0296 1.0000 Uani . . . . . .
C8 C 0.7760(3) 0.9345(2) 1.02415(19) 0.0288 1.0000 Uani . . . . . .
C9 C 0.8609(3) 1.0259(2) 1.1176(2) 0.0372 1.0000 Uani . . . . . .
C10 C 0.9808(4) 0.9890(3) 1.2043(2) 0.0467 1.0000 Uani . . . . . .
C11 C 1.0241(4) 0.8613(3) 1.1997(2) 0.0461 1.0000 Uani . . . . . .
C12 C 0.9441(3) 0.7696(2) 1.1083(2) 0.0358 1.0000 Uani . . . . . .
C13 C 0.8143(3) 0.8051(2) 1.02149(19) 0.0285 1.0000 Uani . . . . . .
C14 C 1.1422(4) 0.6081(4) 1.1445(4) 0.0739 1.0000 Uani . . . . . .
C15 C 0.8989(3) 0.6642(3) 0.7205(3) 0.0482 1.0000 Uani . . . . . .
C16 C 1.0079(3) 0.6052(3) 0.6488(3) 0.0534 1.0000 Uani . . . . . .
C17 C 0.9441(3) 0.5359(2) 0.5389(2) 0.0351 1.0000 Uani . . . . . .
C18 C 0.7709(4) 0.5376(4) 0.5030(3) 0.0576 1.0000 Uani . . . . . .
C19 C 0.6723(4) 0.6027(4) 0.5792(3) 0.0576 1.0000 Uani . . . . . .
C20 C 0.3904(4) 0.4499(3) 0.8377(3) 0.0575 1.0000 Uani . . . . . .
H71 H 0.6562 1.0659 0.9309 0.0358 1.0000 Uiso R . . . . .
H91 H 0.8350 1.1108 1.1182 0.0446 1.0000 Uiso R . . . . .
H101 H 1.0342 1.0495 1.2675 0.0565 1.0000 Uiso R . . . . .
H111 H 1.1075 0.8387 1.2580 0.0544 1.0000 Uiso R . . . . .
H143 H 1.2306 0.6656 1.1282 0.1111 1.0000 Uiso R . . . . .
H142 H 1.1543 0.5170 1.1124 0.1104 1.0000 Uiso R . . . . .
H141 H 1.1415 0.6184 1.2309 0.1112 1.0000 Uiso R . . . . .
H51 H 0.5426 1.1425 0.7690 0.0616 1.0000 Uiso R . . . . .
H41 H 0.3626 1.1881 0.6009 0.0837 1.0000 Uiso R . . . . .
H31 H 0.1935 1.0294 0.4743 0.0839 1.0000 Uiso R . . . . .
H21 H 0.2030 0.8177 0.5106 0.0630 1.0000 Uiso R . . . . .
H201 H 0.3235 0.4966 0.8916 0.0867 1.0000 Uiso R . . . . .
H202 H 0.4572 0.3903 0.8783 0.0861 1.0000 Uiso R . . . . .
H203 H 0.3168 0.4025 0.7710 0.0862 1.0000 Uiso R . . . . .
H191 H 0.5571 0.6064 0.5525 0.0693 1.0000 Uiso R . . . . .
H181 H 0.7198 0.4961 0.4291 0.0687 1.0000 Uiso R . . . . .
H161 H 1.1238 0.6150 0.6757 0.0641 1.0000 Uiso R . . . . .
H151 H 0.9441 0.7083 0.7947 0.0586 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.20470(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 . O1 . 1.9064(17) yes
V1 . O2 . 1.8602(15) yes
V1 . O3 . 1.5975(17) yes
V1 . O5 . 1.7760(16) yes
V1 . N1 . 2.1603(19) yes
V1 . N2 . 2.4772(19) yes
O1 . C1 . 1.328(3) yes
O2 . C13 . 1.328(3) yes
O4 . C12 . 1.356(3) yes
O4 . C14 . 1.406(4) yes
O5 . C20 . 1.411(4) yes
N1 . C6 . 1.416(3) yes
N1 . C7 . 1.284(3) yes
N2 . C15 . 1.310(3) yes
N2 . C19 . 1.334(3) yes
C1 . C2 . 1.399(3) yes
C1 . C6 . 1.399(4) yes
C2 . C3 . 1.378(5) yes
C2 . H21 . 0.955 no
C3 . C4 . 1.381(5) yes
C3 . H31 . 0.934 no
C4 . C5 . 1.387(4) yes
C4 . H41 . 0.918 no
C5 . C6 . 1.382(4) yes
C5 . H51 . 0.942 no
C7 . C8 . 1.437(3) yes
C7 . H71 . 0.922 no
C8 . C9 . 1.407(3) yes
C8 . C13 . 1.400(3) yes
C9 . C10 . 1.363(4) yes
C9 . H91 . 0.921 no
C10 . C11 . 1.392(4) yes
C10 . H101 . 0.932 no
C11 . C12 . 1.382(4) yes
C11 . H111 . 0.921 no
C12 . C13 . 1.407(3) yes
C14 . H143 . 0.981 no
C14 . H142 . 0.991 no
C14 . H141 . 0.974 no
C15 . C16 . 1.380(3) yes
C15 . H151 . 0.920 no
C16 . C17 . 1.374(3) yes
C16 . H161 . 0.926 no
C17 . C17 2_766 1.494(4) yes
C17 . C18 . 1.376(4) yes
C18 . C19 . 1.380(4) yes
C18 . H181 . 0.920 no
C19 . H191 . 0.923 no
C20 . H201 . 0.964 no
C20 . H202 . 0.952 no
C20 . H203 . 0.955 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . V1 . O2 . 150.40(8) yes
O1 . V1 . O3 . 102.26(8) yes
O2 . V1 . O3 . 99.89(8) yes
O1 . V1 . O5 . 93.14(8) yes
O2 . V1 . O5 . 101.92(8) yes
O3 . V1 . O5 . 100.43(9) yes
O1 . V1 . N1 . 77.08(7) yes
O2 . V1 . N1 . 83.03(7) yes
O3 . V1 . N1 . 91.35(8) yes
O5 . V1 . N1 . 166.13(8) yes
O1 . V1 . N2 . 79.91(7) yes
O2 . V1 . N2 . 77.65(7) yes
O3 . V1 . N2 . 177.49(8) yes
O5 . V1 . N2 . 80.62(8) yes
N1 . V1 . N2 . 87.91(7) yes
V1 . O1 . C1 . 121.20(15) yes
V1 . O2 . C13 . 132.50(14) yes
C12 . O4 . C14 . 118.5(2) yes
V1 . O5 . C20 . 128.88(19) yes
V1 . N1 . C6 . 112.29(15) yes
V1 . N1 . C7 . 124.52(15) yes
C6 . N1 . C7 . 122.2(2) yes
V1 . N2 . C15 . 124.36(17) yes
V1 . N2 . C19 . 117.75(17) yes
C15 . N2 . C19 . 115.8(2) yes
O1 . C1 . C2 . 122.5(2) yes
O1 . C1 . C6 . 117.9(2) yes
C2 . C1 . C6 . 119.6(3) yes
C1 . C2 . C3 . 118.8(3) yes
C1 . C2 . H21 . 119.6 no
C3 . C2 . H21 . 121.6 no
C2 . C3 . C4 . 121.3(3) yes
C2 . C3 . H31 . 118.9 no
C4 . C3 . H31 . 119.7 no
C3 . C4 . C5 . 120.5(3) yes
C3 . C4 . H41 . 120.3 no
C5 . C4 . H41 . 119.2 no
C4 . C5 . C6 . 118.9(3) yes
C4 . C5 . H51 . 120.6 no
C6 . C5 . H51 . 120.4 no
N1 . C6 . C1 . 111.4(2) yes
N1 . C6 . C5 . 127.7(2) yes
C1 . C6 . C5 . 120.9(2) yes
N1 . C7 . C8 . 124.2(2) yes
N1 . C7 . H71 . 119.2 no
C8 . C7 . H71 . 116.5 no
C7 . C8 . C9 . 118.6(2) yes
C7 . C8 . C13 . 121.53(19) yes
C9 . C8 . C13 . 119.5(2) yes
C8 . C9 . C10 . 120.3(2) yes
C8 . C9 . H91 . 118.7 no
C10 . C9 . H91 . 121.0 no
C9 . C10 . C11 . 120.5(2) yes
C9 . C10 . H101 . 120.0 no
C11 . C10 . H101 . 119.5 no
C10 . C11 . C12 . 120.5(2) yes
C10 . C11 . H111 . 119.1 no
C12 . C11 . H111 . 120.4 no
C11 . C12 . O4 . 125.3(2) yes
C11 . C12 . C13 . 119.7(2) yes
O4 . C12 . C13 . 115.1(2) yes
C12 . C13 . C8 . 119.4(2) yes
C12 . C13 . O2 . 117.8(2) yes
C8 . C13 . O2 . 122.64(19) yes
O4 . C14 . H143 . 110.0 no
O4 . C14 . H142 . 107.4 no
H143 . C14 . H142 . 113.5 no
O4 . C14 . H141 . 105.7 no
H143 . C14 . H141 . 109.2 no
H142 . C14 . H141 . 110.6 no
N2 . C15 . C16 . 124.0(2) yes
N2 . C15 . H151 . 117.2 no
C16 . C15 . H151 . 118.8 no
C15 . C16 . C17 . 120.1(2) yes
C15 . C16 . H161 . 118.6 no
C17 . C16 . H161 . 121.2 no
C17 2_766 C17 . C16 . 122.1(3) yes
C17 2_766 C17 . C18 . 121.6(3) yes
C16 . C17 . C18 . 116.3(2) yes
C17 . C18 . C19 . 119.4(2) yes
C17 . C18 . H181 . 121.1 no
C19 . C18 . H181 . 119.4 no
C18 . C19 . N2 . 124.0(2) yes
C18 . C19 . H191 . 118.5 no
N2 . C19 . H191 . 117.5 no
O5 . C20 . H201 . 111.3 no
O5 . C20 . H202 . 109.5 no
H201 . C20 . H202 . 109.6 no
O5 . C20 . H203 . 109.0 no
H201 . C20 . H203 . 109.6 no
H202 . C20 . H203 . 107.8 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C7 . H71 . O3 2_677 143.23(6) 0.922 2.585 3.369(4) yes
C16 . H161 . O1 1_655 149.56(10) 0.926 2.443 3.275(4) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-2 0 2 x .
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound1
_database_code_depnum_ccdc_archive 'CCDC 1914116'
loop_
_audit_author_name
_audit_author_address
'Vassilis Psycharis'
;Institute of Nanoscience and Nanotechology, NCSR Demokritos
Greece
;
_audit_update_record             
;
2019-05-06 deposited with the CCDC.	2019-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N O6 V'
_chemical_formula_weight         371.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.0687 2.1097 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/a'
_space_group_name_Hall           '-P 2yab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   7.12280(10)
_cell_length_b                   22.3349(5)
_cell_length_c                   10.4326(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.5660(10)
_cell_angle_gamma                90
_cell_volume                     1631.55(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    8080
_cell_measurement_theta_min      6.63
_cell_measurement_theta_max      71.92

_exptl_crystal_description       parallelepided
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    5.381
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrystalClear, Rigaku MSC, 2005'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   
;
fine-focus sealed tube with graphite monochromator
;
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IPDS'
_diffrn_measurement_method       'θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10727
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         6.625
_diffrn_reflns_theta_max         64.987
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.892
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.892
_reflns_number_total             2642
_reflns_number_gt                2100
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear, Rigaku MSC, 2005'
_computing_cell_refinement       'CrystalClear, Rigaku MSC, 2005'
_computing_data_reduction        'CrystalClear, Rigaku MSC, 2005'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0760P)²+1.2517P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2642
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V V 0.47866(8) 0.14120(3) 0.68956(6) 0.0233(2) Uani 1 1 d . . . . .
N N 0.3532(4) 0.10000(14) 0.5058(3) 0.0233(7) Uani 1 1 d . . . . .
O1 O 0.5386(3) 0.19822(11) 0.5628(2) 0.0255(6) Uani 1 1 d . . . . .
O2 O 0.3203(3) 0.08838(12) 0.7575(2) 0.0250(6) Uani 1 1 d . . . . .
O3 O 0.2627(4) 0.01831(12) 0.9495(2) 0.0327(7) Uani 1 1 d . . . . .
C1 C 0.4782(5) 0.18852(18) 0.4347(3) 0.0256(9) Uani 1 1 d . . . . .
C2 C 0.5177(5) 0.2279(2) 0.3390(4) 0.0295(10) Uani 1 1 d . . . . .
C3 C 0.4490(6) 0.2148(2) 0.2091(4) 0.0359(11) Uani 1 1 d . . . . .
C4 C 0.3404(6) 0.1645(2) 0.1726(4) 0.0375(11) Uani 1 1 d . . . . .
C5 C 0.3009(6) 0.1250(2) 0.2669(4) 0.0333(10) Uani 1 1 d . . . . .
C6 C 0.3714(5) 0.13664(17) 0.3977(3) 0.0241(9) Uani 1 1 d . . . . .
C7 C 0.2874(5) 0.04646(18) 0.4938(4) 0.0248(9) Uani 1 1 d . . . . .
C8 C 0.2619(5) 0.00878(18) 0.6010(3) 0.0262(9) Uani 1 1 d . . . . .
C9 C 0.2109(5) -0.0516(2) 0.5767(4) 0.0309(10) Uani 1 1 d . . . . .
C10 C 0.1790(6) -0.0889(2) 0.6750(4) 0.0349(10) Uani 1 1 d . . . . .
C11 C 0.1962(5) -0.0667(2) 0.8013(4) 0.0326(10) Uani 1 1 d . . . . .
C12 C 0.2437(5) -0.00753(18) 0.8294(4) 0.0270(9) Uani 1 1 d . . . . .
C13 C 0.2782(5) 0.03139(18) 0.7283(4) 0.0260(9) Uani 1 1 d . . . . .
C14 C 0.2646(6) -0.0217(2) 1.0564(4) 0.0398(11) Uani 1 1 d . . . . .
H14A H 0.2788 0.0012 1.1377 0.060 Uiso 1 1 calc R U . . .
H14B H 0.1445 -0.0443 1.0438 0.060 Uiso 1 1 calc R U . . .
H14C H 0.3718 -0.0497 1.0611 0.060 Uiso 1 1 calc R U . . .
O21 O 0.5399(3) 0.19210(12) 0.8205(2) 0.0297(7) Uani 1 1 d . . . . .
C21 C 0.7125(6) 0.2001(2) 0.9125(4) 0.0412(11) Uani 1 1 d . . . . .
H21A H 0.6962 0.2328 0.9722 0.062 Uiso 1 1 calc R U . . .
H21B H 0.7433 0.1630 0.9623 0.062 Uiso 1 1 calc R U . . .
H21C H 0.8166 0.2099 0.8664 0.062 Uiso 1 1 calc R U . . .
O22 O 0.1957(4) 0.19293(15) 0.6469(3) 0.0307(7) Uani 1 1 d . . . . .
C22 C 0.0123(5) 0.1721(2) 0.6588(5) 0.0451(12) Uani 1 1 d . . . . .
H22A H -0.0815 0.2041 0.6339 0.068 Uiso 1 1 calc R U . . .
H22B H -0.0214 0.1375 0.6015 0.068 Uiso 1 1 calc R U . . .
H22C H 0.0129 0.1603 0.7494 0.068 Uiso 1 1 calc R U . . .
O O 0.6633(3) 0.10005(12) 0.7054(2) 0.0287(6) Uani 1 1 d . . . . .
H22O H 0.189(5) 0.2240(18) 0.625(4) 0.016(12) Uiso 1 1 d . . . . .
H2 H 0.594(5) 0.2593(18) 0.362(4) 0.031(12) Uiso 1 1 d . . . . .
H3 H 0.477(5) 0.2458(19) 0.148(4) 0.041(12) Uiso 1 1 d . . . . .
H4 H 0.294(5) 0.1561(17) 0.081(4) 0.032(11) Uiso 1 1 d . . . . .
H5 H 0.226(6) 0.090(2) 0.247(4) 0.047(14) Uiso 1 1 d . . . . .
H7 H 0.263(5) 0.0284(16) 0.411(3) 0.021(9) Uiso 1 1 d . . . . .
H9 H 0.201(4) -0.0685(15) 0.492(3) 0.018(9) Uiso 1 1 d . . . . .
H10 H 0.152(6) -0.131(2) 0.658(4) 0.038(12) Uiso 1 1 d . . . . .
H11 H 0.173(6) -0.094(2) 0.868(4) 0.045(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 O 1.588(3) . ?
V O21 1.769(3) . ?
V O2 1.860(2) . ?
V O1 1.939(2) . ?
V N 2.166(3) . ?
V O22 2.295(3) . ?
N C7 1.282(5) . ?
N C6 1.418(4) . ?
O1 C1 1.345(4) . ?
O2 C13 1.330(4) . ?
O3 C12 1.363(4) . ?
O3 C14 1.429(4) . ?
C1 C2 1.398(5) . ?
C1 C6 1.401(5) . ?
C2 C3 1.385(5) . ?
C2 H2 0.89(4) . ?
C3 C4 1.376(6) . ?
C3 H3 0.99(4) . ?
C4 C5 1.388(6) . ?
C4 H4 0.97(4) . ?
C5 C6 1.389(5) . ?
C5 H5 0.96(5) . ?
C7 C8 1.437(5) . ?
C7 H7 0.94(3) . ?
C8 C13 1.406(5) . ?
C8 C9 1.408(6) . ?
C9 C10 1.372(6) . ?
C9 H9 0.95(3) . ?
C10 C11 1.392(6) . ?
C10 H10 0.97(4) . ?
C11 C12 1.383(6) . ?
C11 H11 0.96(4) . ?
C12 C13 1.422(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O21 C21 1.426(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O22 C22 1.413(4) . ?
O22 H22O 0.73(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
O V O21 102.10(13) . . ?
O V O2 98.15(13) . . ?
O21 V O2 101.19(11) . . ?
O V O1 99.75(12) . . ?
O21 V O1 92.88(11) . . ?
O2 V O1 154.33(11) . . ?
O V N 92.60(12) . . ?
O21 V N 163.65(12) . . ?
O2 V N 83.53(11) . . ?
O1 V N 77.43(11) . . ?
O V O22 173.06(12) . . ?
O21 V O22 84.82(11) . . ?
O2 V O22 79.68(11) . . ?
O1 V O22 80.36(11) . . ?
N V O22 80.62(11) . . ?
C7 N C6 123.0(3) . . ?
C7 N V 124.5(2) . . ?
C6 N V 112.1(2) . . ?
C1 O1 V 120.1(2) . . ?
C13 O2 V 130.3(2) . . ?
C12 O3 C14 116.0(3) . . ?
O1 C1 C2 122.6(4) . . ?
O1 C1 C6 117.8(3) . . ?
C2 C1 C6 119.6(3) . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2 121(3) . . ?
C1 C2 H2 120(3) . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 H3 124(2) . . ?
C2 C3 H3 114(2) . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120(2) . . ?
C5 C4 H4 120(2) . . ?
C4 C5 C6 119.6(4) . . ?
C4 C5 H5 123(3) . . ?
C6 C5 H5 117(3) . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 N 127.2(4) . . ?
C1 C6 N 112.5(3) . . ?
N C7 C8 124.5(3) . . ?
N C7 H7 119(2) . . ?
C8 C7 H7 116(2) . . ?
C13 C8 C9 119.2(4) . . ?
C13 C8 C7 121.6(4) . . ?
C9 C8 C7 119.1(3) . . ?
C10 C9 C8 121.3(4) . . ?
C10 C9 H9 117(2) . . ?
C8 C9 H9 121(2) . . ?
C9 C10 C11 119.6(4) . . ?
C9 C10 H10 120(3) . . ?
C11 C10 H10 120(3) . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 H11 121(3) . . ?
C10 C11 H11 118(3) . . ?
O3 C12 C11 125.3(3) . . ?
O3 C12 C13 114.9(3) . . ?
C11 C12 C13 119.8(4) . . ?
O2 C13 C8 122.4(3) . . ?
O2 C13 C12 118.5(3) . . ?
C8 C13 C12 119.0(4) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 O21 V 131.3(3) . . ?
O21 C21 H21A 109.5 . . ?
O21 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O21 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 O22 V 127.6(3) . . ?
C22 O22 H22O 110(3) . . ?
V O22 H22O 123(3) . . ?
O22 C22 H22A 109.5 . . ?
O22 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O22 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
O22 H22O O1 0.73(4) 2.08(4) 2.752(4) 153(4) 4_565
C22 H22C O2 0.98 2.70 2.922(5) 92.8 .
C22 H22A O1 0.98 2.51 3.081(5) 117.4 4_565
O22 H22O O1 0.73(4) 2.08(4) 2.752(4) 153(4) 4_565

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.080

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1898797'
loop_
_audit_author_name
_audit_author_address
'Antonios HATZIDIMITRIOU'
;Aristotle University of Thessaloniki
Greece
;
_audit_update_record             
;
2019-02-22 deposited with the CCDC.	2019-10-15 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.2356(4)
_cell_length_b                   21.3942(13)
_cell_length_c                   19.5771(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.594(4)
_cell_angle_gamma                90
_cell_volume                     2978.9(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
V 0.3005 0.5294 10.2971 6.8657 7.3511 0.4385 2.0703 26.8938 2.0571 102.4780
1.2199 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C15 H7.50 N1.50 O3 V0.75 
# Dc =      1.32 Fooo =   1194.00 Mu =      5.25 M =    294.94
# Found Formula = C15 H16 N1 O5 V1 
# Dc =      1.52 FOOO =   1408.00 Mu =      6.89 M =    341.24

_chemical_formula_sum            'C15 H16 N1 O5 V1'
_chemical_formula_moiety         'C15 H16 N1 O5 V1'
_chemical_compound_source        ?
_chemical_formula_weight         341.24


_cell_measurement_reflns_used    219
_cell_measurement_theta_min      10
_cell_measurement_theta_max      20
_cell_measurement_temperature    295

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_min          0.130
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_max          0.260

_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.689

# Sheldrick geometric approximatio 0.86 0.91 
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.91
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      295
_diffrn_reflns_number            46827
_reflns_number_total             5992
_diffrn_reflns_av_R_equivalents  0.057
# Number of reflections without Friedels Law is 7418 
# Number of reflections with Friedels Law is 5992 
# Theoretical number of reflections is about 6125 


_diffrn_reflns_theta_min         1.423
_diffrn_reflns_theta_max         26.423
_diffrn_measured_fraction_theta_max 0.980

_diffrn_reflns_theta_full        25.102
_diffrn_measured_fraction_theta_full 0.987


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              -9
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              26
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   -1.33
_oxford_diffrn_Wilson_scale      813.38

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.42
_refine_diff_density_max         0.67


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     0
_refine_ls_number_parameters     397
_oxford_refine_ls_R_factor_ref   0.0520
_refine_ls_wR_factor_ref         0.1117
_refine_ls_goodness_of_fit_ref   0.9999
_refine_ls_shift/su_max          0.0002554
_refine_ls_shift/su_mean         0.0000191


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5967
_refine_ls_R_factor_all          0.0810
_refine_ls_wR_factor_all         0.1332

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4139
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_gt          0.1117

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 3.19 3.96 1.24 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
V1 V 1.01385(16) 0.70486(4) 0.36670(5) 0.0362 1.0000 Uani . . . . . .
V2 V 0.51870(14) 0.46788(4) 0.35105(4) 0.0313 1.0000 Uani . . . . . .
O1 O 1.0752(6) 0.64689(19) 0.2994(2) 0.0425 1.0000 Uani . . . . . .
O2 O 0.8488(7) 0.75535(18) 0.4043(2) 0.0474 1.0000 Uani . . . . . .
O3 O 1.1880(6) 0.7505(2) 0.3759(2) 0.0501 1.0000 Uani . . . . . .
O4 O 1.0768(7) 0.65175(19) 0.4359(2) 0.0496 1.0000 Uani . . . . . .
O5 O 0.7306(6) 0.64476(18) 0.3418(2) 0.0481 1.0000 Uani . . . . . .
O6 O 0.5755(6) 0.52937(18) 0.28571(18) 0.0381 1.0000 Uani . . . . . .
O7 O 0.3604(7) 0.41496(16) 0.38803(19) 0.0412 1.0000 Uani . . . . . .
O8 O 0.6959(6) 0.42345(19) 0.3555(2) 0.0413 1.0000 Uani . . . . . .
O9 O 0.5859(6) 0.51838(18) 0.42220(18) 0.0403 1.0000 Uani . . . . . .
O10 O 0.2361(6) 0.52805(18) 0.3349(2) 0.0444 1.0000 Uani . . . . . .
N1 N 0.8843(7) 0.7461(2) 0.2690(3) 0.0392 1.0000 Uani . . . . . .
N2 N 0.3819(6) 0.4299(2) 0.2533(2) 0.0324 1.0000 Uani . . . . . .
C1 C 1.0195(9) 0.6565(3) 0.2309(3) 0.0393 1.0000 Uani . . . . . .
C2 C 1.0666(9) 0.6150(3) 0.1814(3) 0.0465 1.0000 Uani . . . . . .
C3 C 1.0011(11) 0.6277(3) 0.1123(4) 0.0555 1.0000 Uani . . . . . .
C4 C 0.8966(11) 0.6798(4) 0.0915(3) 0.0577 1.0000 Uani . . . . . .
C5 C 0.8520(10) 0.7209(3) 0.1406(4) 0.0503 1.0000 Uani . . . . . .
C6 C 0.9137(9) 0.7093(3) 0.2097(3) 0.0397 1.0000 Uani . . . . . .
C7 C 0.8061(9) 0.7988(3) 0.2618(3) 0.0399 1.0000 Uani . . . . . .
C8 C 0.7641(8) 0.8347(3) 0.3189(3) 0.0377 1.0000 Uani . . . . . .
C9 C 0.6885(9) 0.8945(3) 0.3037(3) 0.0446 1.0000 Uani . . . . . .
C10 C 0.6349(10) 0.9309(3) 0.3537(4) 0.0490 1.0000 Uani . . . . . .
C11 C 0.6505(11) 0.9075(3) 0.4200(4) 0.0510 1.0000 Uani . . . . . .
C12 C 0.7208(10) 0.8494(3) 0.4372(3) 0.0486 1.0000 Uani . . . . . .
C13 C 0.7827(9) 0.8123(2) 0.3873(3) 0.0379 1.0000 Uani . . . . . .
C14 C 1.2396(12) 0.6496(4) 0.4882(4) 0.0734 1.0000 Uani . . . . . .
C15 C 0.5513(10) 0.6632(3) 0.3520(5) 0.0691 1.0000 Uani . . . . . .
C16 C 0.5150(8) 0.5210(3) 0.2171(3) 0.0347 1.0000 Uani . . . . . .
C17 C 0.5588(9) 0.5625(3) 0.1684(3) 0.0431 1.0000 Uani . . . . . .
C18 C 0.4940(11) 0.5515(3) 0.0994(3) 0.0530 1.0000 Uani . . . . . .
C19 C 0.3875(11) 0.4994(4) 0.0777(3) 0.0561 1.0000 Uani . . . . . .
C20 C 0.3453(9) 0.4569(3) 0.1259(3) 0.0481 1.0000 Uani . . . . . .
C21 C 0.4096(8) 0.4676(3) 0.1962(3) 0.0336 1.0000 Uani . . . . . .
C22 C 0.3006(8) 0.3770(3) 0.2449(3) 0.0355 1.0000 Uani . . . . . .
C23 C 0.2584(8) 0.3389(2) 0.3009(3) 0.0333 1.0000 Uani . . . . . .
C24 C 0.1754(9) 0.2805(3) 0.2844(4) 0.0477 1.0000 Uani . . . . . .
C25 C 0.1203(10) 0.2442(3) 0.3342(4) 0.0565 1.0000 Uani . . . . . .
C26 C 0.1458(10) 0.2653(3) 0.4017(4) 0.0565 1.0000 Uani . . . . . .
C27 C 0.2264(9) 0.3218(3) 0.4201(4) 0.0468 1.0000 Uani . . . . . .
C28 C 0.2867(8) 0.3595(2) 0.3698(3) 0.0353 1.0000 Uani . . . . . .
C29 C 0.7542(9) 0.5224(4) 0.4708(3) 0.0543 1.0000 Uani . . . . . .
C30 C 0.0523(9) 0.5061(3) 0.3330(4) 0.0545 1.0000 Uani . . . . . .
H21 H 1.1384 0.5796 0.1951 0.0547 1.0000 Uiso R . . . . .
H31 H 1.0288 0.5998 0.0794 0.0670 1.0000 Uiso R . . . . .
H41 H 0.8564 0.6873 0.0450 0.0668 1.0000 Uiso R . . . . .
H51 H 0.7823 0.7563 0.1267 0.0608 1.0000 Uiso R . . . . .
H71 H 0.7714 0.8148 0.2160 0.0490 1.0000 Uiso R . . . . .
H91 H 0.6744 0.9095 0.2581 0.0532 1.0000 Uiso R . . . . .
H101 H 0.5863 0.9710 0.3433 0.0580 1.0000 Uiso R . . . . .
H111 H 0.6125 0.9322 0.4539 0.0611 1.0000 Uiso R . . . . .
H121 H 0.7279 0.8346 0.4818 0.0580 1.0000 Uiso R . . . . .
H141 H 1.2034 0.6436 0.5324 0.1100 1.0000 Uiso R . . . . .
H142 H 1.3191 0.6160 0.4794 0.1100 1.0000 Uiso R . . . . .
H143 H 1.3078 0.6880 0.4887 0.1099 1.0000 Uiso R . . . . .
H151 H 0.5187 0.6403 0.3902 0.1071 1.0000 Uiso R . . . . .
H152 H 0.4597 0.6547 0.3110 0.1069 1.0000 Uiso R . . . . .
H153 H 0.5496 0.7069 0.3621 0.1069 1.0000 Uiso R . . . . .
H171 H 0.6296 0.5978 0.1829 0.0508 1.0000 Uiso R . . . . .
H181 H 0.5209 0.5804 0.0670 0.0630 1.0000 Uiso R . . . . .
H191 H 0.3440 0.4932 0.0309 0.0679 1.0000 Uiso R . . . . .
H201 H 0.2770 0.4210 0.1113 0.0567 1.0000 Uiso R . . . . .
H221 H 0.2643 0.3619 0.1993 0.0425 1.0000 Uiso R . . . . .
H241 H 0.1584 0.2667 0.2388 0.0560 1.0000 Uiso R . . . . .
H251 H 0.0658 0.2052 0.3224 0.0681 1.0000 Uiso R . . . . .
H261 H 0.1071 0.2403 0.4352 0.0670 1.0000 Uiso R . . . . .
H271 H 0.2428 0.3352 0.4658 0.0560 1.0000 Uiso R . . . . .
H291 H 0.8127 0.5619 0.4654 0.0833 1.0000 Uiso R . . . . .
H292 H 0.7260 0.5192 0.5168 0.0829 1.0000 Uiso R . . . . .
H293 H 0.8377 0.4892 0.4636 0.0830 1.0000 Uiso R . . . . .
H301 H -0.0274 0.5190 0.2908 0.0821 1.0000 Uiso R . . . . .
H302 H 0.0055 0.5237 0.3715 0.0823 1.0000 Uiso R . . . . .
H303 H 0.0500 0.4616 0.3367 0.0821 1.0000 Uiso R . . . . .
H304 H 0.7272 0.6082 0.3290 0.0719 1.0000 Uiso R . . . . .
H305 H 0.2219 0.5640 0.3219 0.0670 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.10672(4)

loop_
_oxford_twin_element_scale_factors
0.500
0.250
0.250
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 . O1 . 1.921(4) yes
V1 . O2 . 1.860(4) yes
V1 . O3 . 1.578(5) yes
V1 . O4 . 1.762(4) yes
V1 . O5 . 2.392(4) yes
V1 . N1 . 2.158(5) yes
V2 . O6 . 1.931(4) yes
V2 . O7 . 1.850(4) yes
V2 . O8 . 1.586(4) yes
V2 . O9 . 1.759(4) yes
V2 . O10 . 2.388(4) yes
V2 . N2 . 2.147(5) yes
O1 . C1 . 1.343(7) yes
O2 . C13 . 1.328(7) yes
O4 . C14 . 1.412(8) yes
O5 . C15 . 1.405(8) yes
O5 . H304 . 0.820 no
O6 . C16 . 1.346(6) yes
O7 . C28 . 1.323(6) yes
O9 . C29 . 1.404(7) yes
O10 . C30 . 1.404(7) yes
O10 . H305 . 0.811 no
N1 . C6 . 1.452(7) yes
N1 . C7 . 1.258(7) yes
N2 . C21 . 1.421(7) yes
N2 . C22 . 1.272(7) yes
C1 . C2 . 1.402(8) yes
C1 . C6 . 1.384(8) yes
C2 . C3 . 1.376(9) yes
C2 . H21 . 0.928 no
C3 . C4 . 1.367(10) yes
C3 . H31 . 0.927 no
C4 . C5 . 1.383(9) yes
C4 . H41 . 0.918 no
C5 . C6 . 1.367(9) yes
C5 . H51 . 0.922 no
C7 . C8 . 1.434(8) yes
C7 . H71 . 0.950 no
C8 . C9 . 1.402(8) yes
C8 . C13 . 1.405(8) yes
C9 . C10 . 1.362(9) yes
C9 . H91 . 0.937 no
C10 . C11 . 1.377(10) yes
C10 . H101 . 0.935 no
C11 . C12 . 1.362(9) yes
C11 . H111 . 0.928 no
C12 . C13 . 1.395(8) yes
C12 . H121 . 0.922 no
C14 . H141 . 0.958 no
C14 . H142 . 0.956 no
C14 . H143 . 0.958 no
C15 . H151 . 0.960 no
C15 . H152 . 0.959 no
C15 . H153 . 0.956 no
C16 . C17 . 1.381(8) yes
C16 . C21 . 1.393(8) yes
C17 . C18 . 1.366(9) yes
C17 . H171 . 0.927 no
C18 . C19 . 1.377(10) yes
C18 . H181 . 0.931 no
C19 . C20 . 1.385(9) yes
C19 . H191 . 0.921 no
C20 . C21 . 1.389(8) yes
C20 . H201 . 0.928 no
C22 . C23 . 1.442(8) yes
C22 . H221 . 0.941 no
C23 . C24 . 1.397(8) yes
C23 . C28 . 1.398(8) yes
C24 . C25 . 1.363(9) yes
C24 . H241 . 0.927 no
C25 . C26 . 1.375(10) yes
C25 . H251 . 0.934 no
C26 . C27 . 1.363(9) yes
C26 . H261 . 0.928 no
C27 . C28 . 1.402(8) yes
C27 . H271 . 0.926 no
C29 . H291 . 0.960 no
C29 . H292 . 0.960 no
C29 . H293 . 0.959 no
C30 . H301 . 0.957 no
C30 . H302 . 0.959 no
C30 . H303 . 0.956 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . V1 . O2 . 153.3(2) yes
O1 . V1 . O3 . 101.4(2) yes
O2 . V1 . O3 . 98.8(2) yes
O1 . V1 . O4 . 92.94(19) yes
O2 . V1 . O4 . 99.5(2) yes
O3 . V1 . O4 . 102.9(2) yes
O1 . V1 . O5 . 79.06(17) yes
O2 . V1 . O5 . 78.73(18) yes
O3 . V1 . O5 . 172.7(2) yes
O4 . V1 . O5 . 84.30(19) yes
O1 . V1 . N1 . 76.90(19) yes
O2 . V1 . N1 . 84.69(19) yes
O3 . V1 . N1 . 93.2(2) yes
O4 . V1 . N1 . 162.5(2) yes
O5 . V1 . N1 . 79.79(17) yes
O6 . V2 . O7 . 153.97(19) yes
O6 . V2 . O8 . 100.2(2) yes
O7 . V2 . O8 . 99.5(2) yes
O6 . V2 . O9 . 92.56(18) yes
O7 . V2 . O9 . 99.60(18) yes
O8 . V2 . O9 . 102.8(2) yes
O6 . V2 . O10 . 80.01(15) yes
O7 . V2 . O10 . 78.74(17) yes
O8 . V2 . O10 . 174.10(19) yes
O9 . V2 . O10 . 83.04(17) yes
O6 . V2 . N2 . 77.69(17) yes
O7 . V2 . N2 . 84.27(17) yes
O8 . V2 . N2 . 93.28(19) yes
O9 . V2 . N2 . 162.49(19) yes
O10 . V2 . N2 . 80.98(16) yes
V1 . O1 . C1 . 121.5(4) yes
V1 . O2 . C13 . 131.4(4) yes
V1 . O4 . C14 . 129.9(5) yes
V1 . O5 . C15 . 126.8(4) yes
V1 . O5 . H304 . 123.5 no
C15 . O5 . H304 . 109.5 no
V2 . O6 . C16 . 120.1(3) yes
V2 . O7 . C28 . 133.7(4) yes
V2 . O9 . C29 . 130.8(4) yes
V2 . O10 . C30 . 127.4(4) yes
V2 . O10 . H305 . 127.5 no
C30 . O10 . H305 . 104.2 no
V1 . N1 . C6 . 112.5(4) yes
V1 . N1 . C7 . 125.4(4) yes
C6 . N1 . C7 . 121.8(5) yes
V2 . N2 . C21 . 112.1(3) yes
V2 . N2 . C22 . 125.3(4) yes
C21 . N2 . C22 . 122.2(5) yes
O1 . C1 . C2 . 121.8(6) yes
O1 . C1 . C6 . 118.1(5) yes
C2 . C1 . C6 . 120.1(6) yes
C1 . C2 . C3 . 118.1(6) yes
C1 . C2 . H21 . 120.7 no
C3 . C2 . H21 . 121.2 no
C2 . C3 . C4 . 121.7(6) yes
C2 . C3 . H31 . 118.4 no
C4 . C3 . H31 . 119.8 no
C3 . C4 . C5 . 119.9(6) yes
C3 . C4 . H41 . 119.6 no
C5 . C4 . H41 . 120.4 no
C4 . C5 . C6 . 119.7(6) yes
C4 . C5 . H51 . 120.1 no
C6 . C5 . H51 . 120.2 no
N1 . C6 . C1 . 110.9(5) yes
N1 . C6 . C5 . 128.6(6) yes
C1 . C6 . C5 . 120.5(6) yes
N1 . C7 . C8 . 123.3(5) yes
N1 . C7 . H71 . 117.6 no
C8 . C7 . H71 . 119.1 no
C7 . C8 . C9 . 117.0(5) yes
C7 . C8 . C13 . 124.2(5) yes
C9 . C8 . C13 . 118.7(5) yes
C8 . C9 . C10 . 121.4(6) yes
C8 . C9 . H91 . 119.0 no
C10 . C9 . H91 . 119.7 no
C9 . C10 . C11 . 119.0(6) yes
C9 . C10 . H101 . 120.9 no
C11 . C10 . H101 . 120.1 no
C10 . C11 . C12 . 121.8(6) yes
C10 . C11 . H111 . 118.9 no
C12 . C11 . H111 . 119.3 no
C11 . C12 . C13 . 120.1(6) yes
C11 . C12 . H121 . 120.0 no
C13 . C12 . H121 . 119.9 no
C8 . C13 . C12 . 119.0(5) yes
C8 . C13 . O2 . 121.3(5) yes
C12 . C13 . O2 . 119.6(5) yes
O4 . C14 . H141 . 109.2 no
O4 . C14 . H142 . 110.1 no
H141 . C14 . H142 . 109.5 no
O4 . C14 . H143 . 109.9 no
H141 . C14 . H143 . 109.4 no
H142 . C14 . H143 . 108.8 no
O5 . C15 . H151 . 109.5 no
O5 . C15 . H152 . 110.1 no
H151 . C15 . H152 . 109.0 no
O5 . C15 . H153 . 110.5 no
H151 . C15 . H153 . 108.8 no
H152 . C15 . H153 . 108.9 no
O6 . C16 . C17 . 122.0(5) yes
O6 . C16 . C21 . 117.5(5) yes
C17 . C16 . C21 . 120.5(5) yes
C16 . C17 . C18 . 119.4(6) yes
C16 . C17 . H171 . 119.7 no
C18 . C17 . H171 . 120.9 no
C17 . C18 . C19 . 121.1(6) yes
C17 . C18 . H181 . 118.8 no
C19 . C18 . H181 . 120.1 no
C18 . C19 . C20 . 120.1(6) yes
C18 . C19 . H191 . 119.6 no
C20 . C19 . H191 . 120.3 no
C19 . C20 . C21 . 119.4(6) yes
C19 . C20 . H201 . 120.4 no
C21 . C20 . H201 . 120.2 no
N2 . C21 . C16 . 112.6(4) yes
N2 . C21 . C20 . 127.9(5) yes
C16 . C21 . C20 . 119.4(5) yes
N2 . C22 . C23 . 124.3(5) yes
N2 . C22 . H221 . 118.0 no
C23 . C22 . H221 . 117.7 no
C22 . C23 . C24 . 118.1(5) yes
C22 . C23 . C28 . 122.8(5) yes
C24 . C23 . C28 . 119.0(5) yes
C23 . C24 . C25 . 121.0(6) yes
C23 . C24 . H241 . 118.9 no
C25 . C24 . H241 . 120.2 no
C24 . C25 . C26 . 119.7(6) yes
C24 . C25 . H251 . 119.8 no
C26 . C25 . H251 . 120.5 no
C25 . C26 . C27 . 121.4(6) yes
C25 . C26 . H261 . 119.1 no
C27 . C26 . H261 . 119.5 no
C26 . C27 . C28 . 119.8(7) yes
C26 . C27 . H271 . 120.2 no
C28 . C27 . H271 . 120.0 no
C27 . C28 . C23 . 119.2(5) yes
C27 . C28 . O7 . 119.2(5) yes
C23 . C28 . O7 . 121.5(5) yes
O9 . C29 . H291 . 108.9 no
O9 . C29 . H292 . 108.9 no
H291 . C29 . H292 . 109.8 no
O9 . C29 . H293 . 110.3 no
H291 . C29 . H293 . 109.4 no
H292 . C29 . H293 . 109.5 no
O10 . C30 . H301 . 110.2 no
O10 . C30 . H302 . 108.5 no
H301 . C30 . H302 . 108.7 no
O10 . C30 . H303 . 111.2 no
H301 . C30 . H303 . 109.6 no
H302 . C30 . H303 . 108.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O8 3_655 150 0.94 2.58 3.428(9) yes
C29 . H292 . O7 2_666 141 0.96 2.51 3.311(9) yes
O5 . H304 . O6 . 151 0.82 2.10 2.847(9) yes
O10 . H305 . O1 1_455 155 0.81 2.07 2.830(9) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-6 20 10 x .
-8 14 8 x .
-9 8 6 x .
-7 16 12 x .
-8 13 10 x .
-9 7 8 x .
-6 10 20 x .
-6 12 19 x .
-8 2 17 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1898798'
loop_
_audit_author_name
_audit_author_address
'Antonios HATZIDIMITRIOU'
;Aristotle University of Thessaloniki
Greece
;
_audit_update_record             
;
2019-02-22 deposited with the CCDC.	2019-10-15 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.3508(5)
_cell_length_b                   21.9513(15)
_cell_length_c                   21.7346(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.504(4)
_cell_angle_gamma                90
_cell_volume                     3503.7(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Na 0.0362 0.0249 4.7626 3.2850 3.1736 8.8422 1.2674 0.3136 1.1128 129.4240
0.6760 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
V 0.3005 0.5294 10.2971 6.8657 7.3511 0.4385 2.0703 26.8938 2.0571 102.4780
1.2199 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C80 H40 N8 Na4 O16 V4 
# Dc =      1.58 Fooo =   1680.00 Mu =      6.21 M =   1664.97
# Found Formula = C68 H66 N4 Na4 O27 V4 
# Dc =      1.58 FOOO =   1708.00 Mu =      6.30 M =   1667.01

_chemical_formula_sum            'C68 H66 N4 Na4 O27 V4'
_chemical_formula_moiety         'C68 H66 N4 Na4 O27 V4'
_chemical_compound_source        ?
_chemical_formula_weight         1667.01


_cell_measurement_reflns_used    192
_cell_measurement_theta_min      10
_cell_measurement_theta_max      20
_cell_measurement_temperature    299

_exptl_crystal_description       bar
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.056
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_max          0.533

_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1708
_exptl_absorpt_coefficient_mu    0.630

# Sheldrick geometric approximatio 0.91 0.97 
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      299
_diffrn_reflns_number            58024
_reflns_number_total             7682
_diffrn_reflns_av_R_equivalents  0.016
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 7682 
# Theoretical number of reflections is about 15996 


_diffrn_reflns_theta_min         1.319
_diffrn_reflns_theta_max         27.442
_diffrn_measured_fraction_theta_max 0.959

_diffrn_reflns_theta_full        25.246
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       28
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              27
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_oxford_diffrn_Wilson_B_factor   2.13
_oxford_diffrn_Wilson_scale      68.60

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.71
_refine_diff_density_max         0.50


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         5051
_refine_ls_number_restraints     0
_refine_ls_number_parameters     487
_oxford_refine_ls_R_factor_ref   0.0485
_refine_ls_wR_factor_ref         0.0966
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_shift/su_max          0.0009043
_refine_ls_shift/su_mean         0.0000242


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7650
_refine_ls_R_factor_all          0.0846
_refine_ls_wR_factor_all         0.1183

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5051
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_gt          0.0966

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed

# WARNING. The IUCr will not accept pure Unit Weights for F-squared refinements 
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Quasi-Unit weights 
 W = 1.0 or 1./4Fsq 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
V1 V 0.03872(9) 0.17159(3) 0.61939(3) 0.0273 1.0000 Uani . . . . . .
V2 V 0.29152(11) 0.12652(3) 0.37897(3) 0.0358 1.0000 Uani . . . . . .
Na1 Na 0.3407(3) 0.18540(9) 0.51584(8) 0.0503 1.0000 Uani . . . . . .
Na2 Na 0.2187(3) 0.02324(10) 0.50685(11) 0.0690 1.0000 Uani . . . . . .
O1 O 0.1987(4) 0.23453(13) 0.59242(12) 0.0375 1.0000 Uani . . . . . .
O2 O 0.0295(4) 0.09922(12) 0.66762(11) 0.0298 1.0000 Uani . . . . . .
O3 O -0.1616(4) 0.20237(13) 0.62177(12) 0.0356 1.0000 Uani . . . . . .
O4 O 0.0586(4) 0.13394(14) 0.55462(12) 0.0407 1.0000 Uani . . . . . .
O5 O 0.2351(4) 0.20403(13) 0.41414(12) 0.0401 1.0000 Uani . . . . . .
O6 O 0.4739(4) 0.08539(13) 0.33529(12) 0.0373 1.0000 Uani . . . . . .
O7 O 0.1026(4) 0.09493(16) 0.35965(13) 0.0473 1.0000 Uani . . . . . .
O8 O 0.3633(5) 0.10048(14) 0.44663(13) 0.0453 1.0000 Uani . . . . . .
O9 O 0.6334(4) 0.22485(15) 0.50790(14) 0.0461 1.0000 Uani . . . . . .
O10 O 0.4871(5) 0.13899(17) 0.61900(16) 0.0593 1.0000 Uani . . . . . .
O11 O 0.4758(5) 0.02381(16) 0.57827(16) 0.0571 1.0000 Uani . . . . . .
O12 O 0.0026(5) 0.00506(15) 0.57527(15) 0.0514 1.0000 Uani . . . . . .
O13 O 0.2644(6) -0.07250(19) 0.49608(19) 0.0807 1.0000 Uani . . . . . .
O14 O 0.7773(8) 0.1728(3) 0.4012(3) 0.0558 0.5000 Uani . . . . . .
N1 N 0.1627(4) 0.20737(13) 0.70541(12) 0.0200 1.0000 Uani . . . . . .
N2 N 0.3024(4) 0.18776(13) 0.30142(13) 0.0216 1.0000 Uani . . . . . .
C1 C 0.2694(5) 0.27532(18) 0.63271(17) 0.0268 1.0000 Uani . . . . . .
C2 C 0.3600(5) 0.32692(17) 0.61446(17) 0.0268 1.0000 Uani . . . . . .
C3 C 0.4315(5) 0.36585(17) 0.65778(18) 0.0290 1.0000 Uani . . . . . .
C4 C 0.4138(5) 0.35441(18) 0.71996(18) 0.0272 1.0000 Uani . . . . . .
C5 C 0.3269(5) 0.30205(16) 0.73767(17) 0.0222 1.0000 Uani . . . . . .
C6 C 0.2561(4) 0.26233(16) 0.69521(15) 0.0191 1.0000 Uani . . . . . .
C7 C 0.1463(5) 0.18436(16) 0.75936(15) 0.0209 1.0000 Uani . . . . . .
C8 C 0.0581(4) 0.12846(16) 0.77354(15) 0.0186 1.0000 Uani . . . . . .
C9 C 0.0247(4) 0.11218(16) 0.83678(15) 0.0198 1.0000 Uani . . . . . .
C10 C 0.0744(5) 0.14979(18) 0.88741(17) 0.0273 1.0000 Uani . . . . . .
C11 C 0.0382(6) 0.1319(2) 0.94617(17) 0.0362 1.0000 Uani . . . . . .
C12 C -0.0430(6) 0.0769(2) 0.9571(2) 0.0392 1.0000 Uani . . . . . .
C13 C -0.0962(5) 0.0393(2) 0.90900(19) 0.0337 1.0000 Uani . . . . . .
C14 C -0.0627(5) 0.05679(16) 0.84828(16) 0.0234 1.0000 Uani . . . . . .
C15 C -0.1175(5) 0.01889(18) 0.79831(18) 0.0297 1.0000 Uani . . . . . .
C16 C -0.0866(5) 0.03398(17) 0.73987(17) 0.0297 1.0000 Uani . . . . . .
C17 C 0.0001(5) 0.08873(17) 0.72644(17) 0.0273 1.0000 Uani . . . . . .
C18 C 0.1855(5) 0.25007(17) 0.37650(17) 0.0289 1.0000 Uani . . . . . .
C19 C 0.1038(6) 0.30251(18) 0.3969(2) 0.0359 1.0000 Uani . . . . . .
C20 C 0.0588(6) 0.3478(2) 0.3581(2) 0.0382 1.0000 Uani . . . . . .
C21 C 0.0903(5) 0.34233(18) 0.29600(19) 0.0304 1.0000 Uani . . . . . .
C22 C 0.1762(5) 0.29081(16) 0.27420(18) 0.0265 1.0000 Uani . . . . . .
C23 C 0.2232(5) 0.24433(16) 0.31382(16) 0.0219 1.0000 Uani . . . . . .
C24 C 0.3502(4) 0.17174(17) 0.24665(15) 0.0222 1.0000 Uani . . . . . .
C25 C 0.4315(5) 0.11632(15) 0.22987(16) 0.0208 1.0000 Uani . . . . . .
C26 C 0.4559(5) 0.10272(17) 0.16663(17) 0.0242 1.0000 Uani . . . . . .
C27 C 0.3934(5) 0.13848(19) 0.11720(17) 0.0306 1.0000 Uani . . . . . .
C28 C 0.4249(5) 0.1245(2) 0.05755(19) 0.0373 1.0000 Uani . . . . . .
C29 C 0.5242(6) 0.0732(2) 0.0441(2) 0.0425 1.0000 Uani . . . . . .
C30 C 0.5859(6) 0.0357(2) 0.08941(19) 0.0359 1.0000 Uani . . . . . .
C31 C 0.5553(5) 0.04834(17) 0.15207(18) 0.0270 1.0000 Uani . . . . . .
C32 C 0.6190(6) 0.01083(19) 0.2003(2) 0.0391 1.0000 Uani . . . . . .
C33 C 0.5913(5) 0.02335(19) 0.2601(2) 0.0336 1.0000 Uani . . . . . .
C34 C 0.4930(5) 0.07561(17) 0.27610(18) 0.0280 1.0000 Uani . . . . . .
H131 H -0.1530 0.0030 0.9159 0.0411 1.0000 Uiso R . . . . .
H121 H -0.0615 0.0651 0.9972 0.0471 1.0000 Uiso R . . . . .
H111 H 0.0681 0.1580 0.9789 0.0444 1.0000 Uiso R . . . . .
H101 H 0.1315 0.1864 0.8812 0.0330 1.0000 Uiso R . . . . .
H151 H -0.1754 -0.0170 0.8060 0.0359 1.0000 Uiso R . . . . .
H161 H -0.1220 0.0075 0.7085 0.0364 1.0000 Uiso R . . . . .
H71 H 0.1981 0.2067 0.7917 0.0252 1.0000 Uiso R . . . . .
H92 H 0.6804 0.2124 0.4763 0.0695 1.0000 Uiso R . . . . .
H91 H 0.6916 0.2184 0.5403 0.0554 1.0000 Uiso R . . . . .
H241 H 0.3310 0.1993 0.2159 0.0274 1.0000 Uiso R . . . . .
H301 H 0.6475 0.0003 0.0795 0.0430 1.0000 Uiso R . . . . .
H291 H 0.5452 0.0646 0.0034 0.0509 1.0000 Uiso R . . . . .
H281 H 0.3811 0.1493 0.0265 0.0449 1.0000 Uiso R . . . . .
H271 H 0.3251 0.1728 0.1251 0.0371 1.0000 Uiso R . . . . .
H321 H 0.6847 -0.0238 0.1907 0.0471 1.0000 Uiso R . . . . .
H331 H 0.6346 -0.0031 0.2903 0.0401 1.0000 Uiso R . . . . .
H221 H 0.1996 0.2875 0.2327 0.0319 1.0000 Uiso R . . . . .
H211 H 0.0541 0.3732 0.2690 0.0370 1.0000 Uiso R . . . . .
H201 H 0.0034 0.3828 0.3728 0.0461 1.0000 Uiso R . . . . .
H191 H 0.0821 0.3058 0.4386 0.0430 1.0000 Uiso R . . . . .
H122 H 0.0121 0.0335 0.6004 0.0622 1.0000 Uiso R . . . . .
H333 H -0.0292 -0.0263 0.5932 0.0622 1.0000 Uiso R . . . . .
H112 H 0.5696 0.0212 0.5592 0.0685 1.0000 Uiso R . . . . .
H334 H 0.4652 0.0078 0.6120 0.0667 1.0000 Uiso R . . . . .
H21 H 0.3690 0.3351 0.5732 0.0323 1.0000 Uiso R . . . . .
H31 H 0.4929 0.4000 0.6459 0.0353 1.0000 Uiso R . . . . .
H41 H 0.4624 0.3817 0.7491 0.0330 1.0000 Uiso R . . . . .
H51 H 0.3160 0.2938 0.7791 0.0268 1.0000 Uiso R . . . . .
H102 H 0.4900 0.1023 0.6070 0.0893 1.0000 Uiso R . . . . .
H335 H 0.5882 0.1539 0.6241 0.0896 1.0000 Uiso R . . . . .
H142 H 0.6998 0.1507 0.3845 0.0640 0.5000 Uiso R . . . . .
H141 H 0.8636 0.1523 0.3903 0.0640 0.5000 Uiso R . . . . .
H132 H 0.2541 -0.0953 0.5256 0.0977 1.0000 Uiso R . . . . .
H135 H 0.1701 -0.0828 0.4703 0.0977 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.12819(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 . O1 . 1.922(3) yes
V1 . O2 . 1.906(3) yes
V1 . O3 . 1.623(3) yes
V1 . O4 . 1.644(3) yes
V1 . N1 . 2.189(3) yes
V2 . O5 . 1.918(3) yes
V2 . O6 . 1.904(3) yes
V2 . O7 . 1.592(3) yes
V2 . O8 . 1.643(3) yes
V2 . N2 . 2.160(3) yes
Na1 . O1 . 2.275(3) yes
Na1 . O4 . 2.537(3) yes
Na1 . O5 . 2.347(3) yes
Na1 . O8 . 2.406(4) yes
Na1 . O9 . 2.333(4) yes
Na1 . O10 . 2.648(4) yes
Na2 . O12 2_556 2.442(4) yes
Na2 . O8 . 2.417(4) yes
Na2 . O11 . 2.393(4) yes
Na2 . O12 . 2.258(4) yes
Na2 . O13 . 2.143(5) yes
O1 . C1 . 1.341(4) yes
O2 . C17 . 1.326(4) yes
O5 . C18 . 1.341(5) yes
O6 . C34 . 1.318(5) yes
O9 . H92 . 0.828 no
O9 . H91 . 0.820 no
O10 . H102 . 0.848 no
O10 . H335 . 0.816 no
O11 . H112 . 0.822 no
O11 . H334 . 0.820 no
O12 . H122 . 0.830 no
O12 . H333 . 0.830 no
O13 . H132 . 0.820 no
O13 . H135 . 0.901 no
O14 . H142 . 0.820 no
O14 . H141 . 0.820 no
N1 . C6 . 1.410(4) yes
N1 . C7 . 1.287(4) yes
N2 . C23 . 1.402(4) yes
N2 . C24 . 1.304(4) yes
C1 . C2 . 1.381(5) yes
C1 . C6 . 1.396(5) yes
C2 . C3 . 1.360(5) yes
C2 . H21 . 0.920 no
C3 . C4 . 1.386(5) yes
C3 . H31 . 0.919 no
C4 . C5 . 1.378(5) yes
C4 . H41 . 0.931 no
C5 . C6 . 1.357(5) yes
C5 . H51 . 0.925 no
C7 . C8 . 1.428(5) yes
C7 . H71 . 0.925 no
C8 . C9 . 1.451(5) yes
C8 . C17 . 1.397(5) yes
C9 . C10 . 1.411(5) yes
C9 . C14 . 1.403(5) yes
C10 . C11 . 1.373(5) yes
C10 . H101 . 0.920 no
C11 . C12 . 1.373(6) yes
C11 . H111 . 0.932 no
C12 . C13 . 1.375(6) yes
C12 . H121 . 0.925 no
C13 . C14 . 1.406(5) yes
C13 . H131 . 0.917 no
C14 . C15 . 1.413(5) yes
C15 . C16 . 1.342(5) yes
C15 . H151 . 0.915 no
C16 . C17 . 1.397(5) yes
C16 . H161 . 0.925 no
C18 . C19 . 1.381(5) yes
C18 . C23 . 1.408(5) yes
C19 . C20 . 1.336(6) yes
C19 . H191 . 0.930 no
C20 . C21 . 1.384(6) yes
C20 . H201 . 0.932 no
C21 . C22 . 1.389(5) yes
C21 . H211 . 0.928 no
C22 . C23 . 1.370(5) yes
C22 . H221 . 0.929 no
C24 . C25 . 1.411(5) yes
C24 . H241 . 0.908 no
C25 . C26 . 1.425(5) yes
C25 . C34 . 1.405(5) yes
C26 . C27 . 1.392(5) yes
C26 . C31 . 1.442(5) yes
C27 . C28 . 1.362(5) yes
C27 . H271 . 0.926 no
C28 . C29 . 1.380(6) yes
C28 . H281 . 0.914 no
C29 . C30 . 1.346(6) yes
C29 . H291 . 0.923 no
C30 . C31 . 1.417(5) yes
C30 . H301 . 0.929 no
C31 . C32 . 1.397(6) yes
C32 . C33 . 1.353(6) yes
C32 . H321 . 0.929 no
C33 . C34 . 1.408(5) yes
C33 . H331 . 0.924 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . V1 . O2 . 143.47(13) yes
O1 . V1 . O3 . 106.17(14) yes
O2 . V1 . O3 . 105.99(13) yes
O1 . V1 . O4 . 91.25(13) yes
O2 . V1 . O4 . 93.35(13) yes
O3 . V1 . O4 . 110.56(15) yes
O1 . V1 . N1 . 76.42(11) yes
O2 . V1 . N1 . 81.54(11) yes
O3 . V1 . N1 . 99.66(12) yes
O4 . V1 . N1 . 149.55(14) yes
O5 . V2 . O6 . 142.05(14) yes
O5 . V2 . O7 . 106.86(16) yes
O6 . V2 . O7 . 106.68(15) yes
O5 . V2 . O8 . 91.06(14) yes
O6 . V2 . O8 . 94.34(14) yes
O7 . V2 . O8 . 109.09(16) yes
O5 . V2 . N2 . 76.99(11) yes
O6 . V2 . N2 . 81.67(12) yes
O7 . V2 . N2 . 97.29(14) yes
O8 . V2 . N2 . 153.30(14) yes
O1 . Na1 . O4 . 63.91(10) yes
O1 . Na1 . O5 . 117.59(14) yes
O4 . Na1 . O5 . 98.57(12) yes
O1 . Na1 . O8 . 150.63(14) yes
O4 . Na1 . O8 . 86.72(12) yes
O5 . Na1 . O8 . 64.86(11) yes
O1 . Na1 . O9 . 109.41(13) yes
O4 . Na1 . O9 . 163.66(13) yes
O5 . Na1 . O9 . 97.69(12) yes
O8 . Na1 . O9 . 98.74(13) yes
O1 . Na1 . O10 . 75.25(12) yes
O4 . Na1 . O10 . 81.68(11) yes
O5 . Na1 . O10 . 165.96(14) yes
O8 . Na1 . O10 . 101.22(13) yes
O9 . Na1 . O10 . 82.15(12) yes
O12 2_556 Na2 . O8 . 94.45(13) yes
O12 2_556 Na2 . O11 . 163.23(17) yes
O8 . Na2 . O11 . 89.65(13) yes
O12 2_556 Na2 . O12 . 88.34(14) yes
O8 . Na2 . O12 . 145.02(16) yes
O11 . Na2 . O12 . 97.59(14) yes
O12 2_556 Na2 . O13 . 76.89(16) yes
O8 . Na2 . O13 . 123.67(18) yes
O11 . Na2 . O13 . 87.30(17) yes
O12 . Na2 . O13 . 90.96(17) yes
Na1 . O1 . V1 . 100.88(13) yes
Na1 . O1 . C1 . 128.1(2) yes
V1 . O1 . C1 . 120.4(2) yes
V1 . O2 . C17 . 133.3(2) yes
Na1 . O4 . V1 . 99.50(14) yes
Na1 . O5 . V2 . 98.76(14) yes
Na1 . O5 . C18 . 140.9(2) yes
V2 . O5 . C18 . 118.9(2) yes
V2 . O6 . C34 . 132.2(3) yes
Na1 . O8 . Na2 . 99.26(13) yes
Na1 . O8 . V2 . 105.18(16) yes
Na2 . O8 . V2 . 126.65(18) yes
Na1 . O9 . H92 . 111.0 no
Na1 . O9 . H91 . 108.7 no
H92 . O9 . H91 . 115.7 no
Na1 . O10 . H102 . 96.9 no
Na1 . O10 . H335 . 107.1 no
H102 . O10 . H335 . 112.8 no
Na2 . O11 . H112 . 109.2 no
Na2 . O11 . H334 . 118.3 no
H112 . O11 . H334 . 122.5 no
Na2 . O12 . Na2 2_556 91.66(14) yes
Na2 . O12 . H122 . 105.0 no
Na2 2_556 O12 . H122 . 134.9 no
Na2 . O12 . H333 . 132.6 no
Na2 2_556 O12 . H333 . 86.5 no
H122 . O12 . H333 . 109.5 no
Na2 . O13 . H132 . 119.6 no
Na2 . O13 . H135 . 101.2 no
H132 . O13 . H135 . 103.8 no
H142 . O14 . H141 . 94.6 no
V1 . N1 . C6 . 111.1(2) yes
V1 . N1 . C7 . 125.8(2) yes
C6 . N1 . C7 . 123.0(3) yes
V2 . N2 . C23 . 111.8(2) yes
V2 . N2 . C24 . 124.4(2) yes
C23 . N2 . C24 . 123.0(3) yes
O1 . C1 . C2 . 122.6(3) yes
O1 . C1 . C6 . 117.2(3) yes
C2 . C1 . C6 . 120.2(3) yes
C1 . C2 . C3 . 119.5(3) yes
C1 . C2 . H21 . 119.7 no
C3 . C2 . H21 . 120.7 no
C2 . C3 . C4 . 120.7(3) yes
C2 . C3 . H31 . 119.9 no
C4 . C3 . H31 . 119.4 no
C3 . C4 . C5 . 119.2(3) yes
C3 . C4 . H41 . 119.8 no
C5 . C4 . H41 . 121.0 no
C4 . C5 . C6 . 121.0(4) yes
C4 . C5 . H51 . 119.7 no
C6 . C5 . H51 . 119.3 no
N1 . C6 . C1 . 112.5(3) yes
N1 . C6 . C5 . 128.2(3) yes
C1 . C6 . C5 . 119.3(3) yes
N1 . C7 . C8 . 126.5(3) yes
N1 . C7 . H71 . 115.6 no
C8 . C7 . H71 . 117.9 no
C7 . C8 . C9 . 120.9(3) yes
C7 . C8 . C17 . 120.4(3) yes
C9 . C8 . C17 . 118.8(3) yes
C8 . C9 . C10 . 123.1(3) yes
C8 . C9 . C14 . 118.7(3) yes
C10 . C9 . C14 . 118.2(3) yes
C9 . C10 . C11 . 120.3(4) yes
C9 . C10 . H101 . 120.0 no
C11 . C10 . H101 . 119.7 no
C10 . C11 . C12 . 121.1(4) yes
C10 . C11 . H111 . 119.0 no
C12 . C11 . H111 . 119.9 no
C11 . C12 . C13 . 120.5(4) yes
C11 . C12 . H121 . 119.5 no
C13 . C12 . H121 . 120.0 no
C12 . C13 . C14 . 119.6(4) yes
C12 . C13 . H131 . 121.0 no
C14 . C13 . H131 . 119.4 no
C13 . C14 . C9 . 120.3(4) yes
C13 . C14 . C15 . 120.3(4) yes
C9 . C14 . C15 . 119.4(3) yes
C14 . C15 . C16 . 121.9(4) yes
C14 . C15 . H151 . 119.1 no
C16 . C15 . H151 . 119.0 no
C15 . C16 . C17 . 120.5(4) yes
C15 . C16 . H161 . 119.3 no
C17 . C16 . H161 . 120.1 no
C16 . C17 . C8 . 120.8(3) yes
C16 . C17 . O2 . 116.5(3) yes
C8 . C17 . O2 . 122.7(3) yes
O5 . C18 . C19 . 122.9(4) yes
O5 . C18 . C23 . 117.6(3) yes
C19 . C18 . C23 . 119.5(4) yes
C18 . C19 . C20 . 121.1(4) yes
C18 . C19 . H191 . 118.2 no
C20 . C19 . H191 . 120.7 no
C19 . C20 . C21 . 120.3(4) yes
C19 . C20 . H201 . 119.7 no
C21 . C20 . H201 . 120.0 no
C20 . C21 . C22 . 120.1(4) yes
C20 . C21 . H211 . 119.8 no
C22 . C21 . H211 . 120.1 no
C21 . C22 . C23 . 119.9(4) yes
C21 . C22 . H221 . 120.1 no
C23 . C22 . H221 . 120.0 no
C18 . C23 . N2 . 111.5(3) yes
C18 . C23 . C22 . 119.1(3) yes
N2 . C23 . C22 . 129.4(3) yes
N2 . C24 . C25 . 127.1(3) yes
N2 . C24 . H241 . 116.9 no
C25 . C24 . H241 . 116.0 no
C24 . C25 . C26 . 120.2(3) yes
C24 . C25 . C34 . 119.4(3) yes
C26 . C25 . C34 . 120.4(3) yes
C25 . C26 . C27 . 125.1(3) yes
C25 . C26 . C31 . 118.1(3) yes
C27 . C26 . C31 . 116.8(3) yes
C26 . C27 . C28 . 122.9(4) yes
C26 . C27 . H271 . 118.6 no
C28 . C27 . H271 . 118.5 no
C27 . C28 . C29 . 120.0(4) yes
C27 . C28 . H281 . 119.9 no
C29 . C28 . H281 . 120.2 no
C28 . C29 . C30 . 120.5(4) yes
C28 . C29 . H291 . 118.8 no
C30 . C29 . H291 . 120.7 no
C29 . C30 . C31 . 121.4(4) yes
C29 . C30 . H301 . 119.5 no
C31 . C30 . H301 . 119.0 no
C26 . C31 . C30 . 118.4(4) yes
C26 . C31 . C32 . 118.7(4) yes
C30 . C31 . C32 . 122.9(4) yes
C31 . C32 . C33 . 122.8(4) yes
C31 . C32 . H321 . 118.3 no
C33 . C32 . H321 . 118.9 no
C32 . C33 . C34 . 120.2(4) yes
C32 . C33 . H331 . 119.6 no
C34 . C33 . H331 . 120.1 no
C33 . C34 . C25 . 119.6(4) yes
C33 . C34 . O6 . 116.9(4) yes
C25 . C34 . O6 . 123.4(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O9 . H92 . O14 . 173 0.83 2.01 2.831(5) yes
O9 . H91 . O3 1_655 180 0.82 2.06 2.883(5) yes
O12 . H122 . O2 . 176 0.83 2.05 2.882(5) yes
O12 . H333 . O7 2_556 175 0.83 1.91 2.741(5) yes
O11 . H112 . O13 2_656 141 0.82 2.08 2.769(5) yes
O11 . H334 . O6 2_656 141 0.82 2.38 3.058(5) yes
O10 . H102 . O11 . 175 0.85 1.83 2.679(5) yes
O10 . H335 . O3 1_655 169 0.82 2.13 2.932(5) yes
O14 . H142 . O6 . 180 0.82 2.41 3.229(5) yes
O14 . H141 . O7 1_655 180 0.82 2.29 3.105(5) yes
O13 . H132 . O14 2_656 171 0.82 2.35 3.159(5) yes
O13 . H135 . O4 2_556 153 0.90 2.07 2.905(5) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
