# 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 2018

####################################################################### 
# 
# 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_l
_audit_block_doi                 10.5517/ccdc.csd.cc1q7spf
_database_code_depnum_ccdc_archive 'CCDC 1586415'
_audit_update_record             
;
2018-03-17 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 Cu N2 O10 V4'
_chemical_formula_sum            'C4 H4 Cu N2 O10 V4'
_chemical_formula_weight         507.40

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'

_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, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'x+1/2, -y+1/2, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   14.243(3)
_cell_length_b                   6.9172(11)
_cell_length_c                   11.5429(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1137.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1606
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      29.90

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.964
_exptl_crystal_F_000             972.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24

_exptl_absorpt_coefficient_mu    5.063
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.199
_exptl_absorpt_correction_T_max  0.297
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5066
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         25.234
_diffrn_reflns_theta_full        25.234
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             571
_reflns_number_gt                510
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0685P)²+3.6065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         572
_refine_ls_number_parameters     58
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.5000 0.18199(16) 0.2500 0.0219(4) Uani 1 4 d S T P . .
V1 V 0.28804(5) 0.13651(11) 0.39585(6) 0.0192(3) Uani 1 1 d . . . . .
N2 N 0.5000 0.4814(10) 0.2500 0.0183(15) Uani 1 4 d S T P . .
O3 O 0.3999(2) 0.1825(5) 0.3760(3) 0.0237(7) Uani 1 1 d . . . . .
O1 O 0.2755(2) 0.1312(4) 0.5695(3) 0.0277(8) Uani 1 1 d . . . . .
N1 N 0.5000 -0.1145(11) 0.2500 0.0242(17) Uani 1 4 d S T P . .
O2 O 0.2418(3) 0.1151(6) 0.2500 0.0241(10) Uani 1 2 d S T P . .
C1 C 0.5000 -0.2177(10) 0.3482(6) 0.0379(18) Uani 1 2 d S T P . .
H1 H 0.5000 -0.1540 0.4192 0.046 Uiso 1 2 calc R U P . .
C2 C 0.5000 0.5841(11) 0.3456(6) 0.044(2) Uani 1 2 d S T P . .
H2 H 0.5000 0.5184 0.4159 0.053 Uiso 1 2 calc R U P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0183(6) 0.0184(7) 0.0290(6) 0.000 0.000 0.000
V1 0.0165(5) 0.0151(5) 0.0259(5) 0.0010(3) 0.0041(3) 0.0000(3)
N2 0.019(4) 0.015(4) 0.021(3) 0.000 0.000 0.000
O3 0.0172(16) 0.0251(18) 0.0287(16) -0.0019(13) 0.0026(13) -0.0007(13)
O1 0.0309(19) 0.0234(19) 0.0288(17) 0.0028(14) 0.0044(15) 0.0079(14)
N1 0.022(4) 0.017(4) 0.033(4) 0.000 0.000 0.000
O2 0.021(2) 0.022(3) 0.029(2) 0.000 0.000 0.0016(19)
C1 0.066(5) 0.018(4) 0.029(3) 0.001(3) 0.000 0.000
C2 0.088(7) 0.016(4) 0.029(4) -0.001(3) 0.000 0.000

_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
Cu1 O3 2.037(3) . ?
Cu1 O3 2.037(3) 12_655 ?
Cu1 O3 2.037(3) 10_556 ?
Cu1 O3 2.037(3) 3_655 ?
Cu1 N1 2.051(7) . ?
Cu1 N2 2.071(7) . ?
V1 O3 1.641(3) . ?
V1 O2 1.8140(18) . ?
V1 O1 1.887(3) 13_556 ?
V1 O1 1.903(3) 4_556 ?
V1 O1 2.013(4) . ?
V1 V1 3.0574(15) 4_556 ?
V1 V1 3.0692(15) 13_556 ?
N2 C2 1.312(8) . ?
N2 C2 1.312(8) 10_556 ?
O1 V1 1.887(3) 13_556 ?
O1 V1 1.903(3) 4_556 ?
N1 C1 1.340(8) . ?
N1 C1 1.340(8) 10_556 ?
O2 V1 1.8140(18) 10_556 ?
C1 C2 1.372(10) 1_545 ?
C2 C1 1.372(10) 1_565 ?

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
O3 Cu1 O3 88.86(17) . 12_655 ?
O3 Cu1 O3 91.13(17) . 10_556 ?
O3 Cu1 O3 179.80(19) 12_655 10_556 ?
O3 Cu1 O3 179.80(19) . 3_655 ?
O3 Cu1 O3 91.14(17) 12_655 3_655 ?
O3 Cu1 O3 88.86(17) 10_556 3_655 ?
O3 Cu1 N1 90.10(9) . . ?
O3 Cu1 N1 90.10(9) 12_655 . ?
O3 Cu1 N1 90.10(9) 10_556 . ?
O3 Cu1 N1 90.10(9) 3_655 . ?
O3 Cu1 N2 89.90(9) . . ?
O3 Cu1 N2 89.90(9) 12_655 . ?
O3 Cu1 N2 89.90(9) 10_556 . ?
O3 Cu1 N2 89.90(9) 3_655 . ?
N1 Cu1 N2 180.0 . . ?
O3 V1 O2 103.82(18) . . ?
O3 V1 O1 109.30(16) . 13_556 ?
O2 V1 O1 95.26(18) . 13_556 ?
O3 V1 O1 107.99(16) . 4_556 ?
O2 V1 O1 94.66(17) . 4_556 ?
O1 V1 O1 137.67(13) 13_556 4_556 ?
O3 V1 O1 103.21(16) . . ?
O2 V1 O1 152.96(17) . . ?
O1 V1 O1 76.24(16) 13_556 . ?
O1 V1 O1 76.41(16) 4_556 . ?
O3 V1 V1 103.28(11) . 4_556 ?
O2 V1 V1 132.79(14) . 4_556 ?
O1 V1 V1 111.06(12) 13_556 4_556 ?
O1 V1 V1 39.98(11) 4_556 4_556 ?
O1 V1 V1 37.40(9) . 4_556 ?
O3 V1 V1 110.68(12) . 13_556 ?
O2 V1 V1 129.84(14) . 13_556 ?
O1 V1 V1 39.57(11) 13_556 13_556 ?
O1 V1 V1 107.48(12) 4_556 13_556 ?
O1 V1 V1 36.67(9) . 13_556 ?
V1 V1 V1 72.54(3) 4_556 13_556 ?
C2 N2 C2 114.5(9) . 10_556 ?
C2 N2 Cu1 122.8(4) . . ?
C2 N2 Cu1 122.8(4) 10_556 . ?
V1 O3 Cu1 141.19(18) . . ?
V1 O1 V1 146.0(2) 13_556 4_556 ?
V1 O1 V1 103.76(16) 13_556 . ?
V1 O1 V1 102.62(16) 4_556 . ?
C1 N1 C1 115.6(8) . 10_556 ?
C1 N1 Cu1 122.2(4) . . ?
C1 N1 Cu1 122.2(4) 10_556 . ?
V1 O2 V1 136.3(3) 10_556 . ?
N1 C1 C2 121.0(7) . 1_545 ?
N2 C2 C1 124.0(7) . 1_565 ?

_refine_diff_density_max         0.665
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.163

_shelx_res_file                  
;

    l.res created by SHELXL-2014/7

TITL L in Cmcm
CELL 0.71073  14.2435   6.9172  11.5429  90.000  90.000  90.000
ZERR   10.00   0.0026   0.0011   0.0018   0.000   0.000   0.000
LATT 7
SYMM -X, -Y, 0.5+Z
SYMM -X, Y, 0.5-Z
SYMM X, -Y, -Z
SFAC C  H  N  O  V  Cu
UNIT 10 10 10 10 10 10
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
OMIT   0.00  50.50
L.S. 10
ACTA
BOND
FMAP 2
PLAN 5
TEMP 23.000
WGHT    0.068500    3.606500
FVAR       0.06184
MOLE 1
CU1   6    0.500000    0.181994    0.250000    10.25000    0.01832    0.01836 =
         0.02899    0.00000    0.00000    0.00000
V1    5    0.288041    0.136513    0.395853    11.00000    0.01648    0.01509 =
         0.02593    0.00096    0.00412    0.00004
N2    3    0.500000    0.481414    0.250000    10.25000    0.01882    0.01496 =
         0.02125    0.00000    0.00000    0.00000
O3    4    0.399897    0.182504    0.375993    11.00000    0.01723    0.02510 =
         0.02874   -0.00185    0.00262   -0.00073
O1    4    0.275547    0.131239    0.569535    11.00000    0.03095    0.02339 =
         0.02876    0.00276    0.00436    0.00790
N1    3    0.500000   -0.114453    0.250000    10.25000    0.02242    0.01674 =
         0.03329    0.00000    0.00000    0.00000
O2    4    0.241781    0.115070    0.250000    10.50000    0.02100    0.02178 =
         0.02945    0.00000    0.00000    0.00160
C1    1    0.500000   -0.217709    0.348196    10.50000    0.06645    0.01832 =
         0.02903    0.00093    0.00000    0.00000
AFIX  43
H1    2    0.500000   -0.154024    0.419153    10.50000   -1.20000
AFIX   0
C2    1    0.500000    0.584057    0.345626    10.50000    0.08772    0.01614 =
         0.02860   -0.00135    0.00000    0.00000
AFIX  43
H2    2    0.500000    0.518375    0.415927    10.50000   -1.20000
AFIX   0
HKLF 4

REM  L in Cmcm
REM R1 =  0.0371 for     510 Fo > 4sig(Fo)  and  0.0415 for all     572 data
REM     58 parameters refined using      0 restraints

END

WGHT      0.0503      3.4622

REM Highest difference peak  0.665,  deepest hole -0.521,  1-sigma level  0.163
Q1    1   0.5000  0.1512  0.3427  10.50000  0.05    0.67
Q2    1   0.5000  0.2400  0.3384  10.50000  0.05    0.65
Q3    1   0.2891  0.1121  0.4883  11.00000  0.05    0.64
Q4    1   0.2945  0.1624  0.2500  10.50000  0.05    0.64
Q5    1   0.5000  0.0294  0.2500  10.25000  0.05    0.56
;
_shelx_res_checksum              74114
