# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_umd702_a
_database_code_depnum_ccdc_archive 'CCDC 2103585'
loop_
_audit_author_name
_audit_author_address
'James Golen'
;University of Massachusetts Dartmouth
United States of America
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Tetramethylammonium vanadium(v)-bis-hydroxyiminodiacetate'
_chemical_name_common            TMAVBH
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H25 N3 O12 V'
_chemical_formula_weight         454.29

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Fddd

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   15.926(2)
_cell_length_b                   18.696(3)
_cell_length_c                   26.925(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8017(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9521
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      26.29

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3792
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8501
_exptl_absorpt_correction_T_max  0.9566
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker cmos'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56007
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         26.41
_reflns_number_total             2073
_reflns_number_gt                1790
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0371P)²+13.0642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2073
_refine_ls_number_parameters     138
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.3750 0.614387(19) 0.3750 0.02002(12) Uani 1 2 d S . .
O1 O 0.47536(7) 0.54530(6) 0.37155(4) 0.0319(3) Uani 1 1 d . . .
O2 O 0.59357(7) 0.52076(6) 0.33081(5) 0.0385(3) Uani 1 1 d . . .
O3 O 0.28298(9) 0.78954(8) 0.30343(5) 0.0508(4) Uani 1 1 d . . .
O4 O 0.29570(6) 0.69614(6) 0.35347(4) 0.0271(2) Uani 1 1 d . . .
O5 O 0.36434(7) 0.58945(6) 0.30423(4) 0.0306(3) Uani 1 1 d . . .
O6 O 0.64323(8) 0.43079(7) 0.39829(5) 0.0382(3) Uani 1 1 d D . .
H6D H 0.6896(11) 0.4397(11) 0.4115(8) 0.046 Uiso 1 1 d D . .
H6E H 0.6284(13) 0.4617(11) 0.3764(7) 0.046 Uiso 1 1 d D . .
N1 N 0.42472(8) 0.64187(7) 0.30970(5) 0.0233(3) Uani 1 1 d . . .
N2 N 0.6250 0.6250 0.51441(8) 0.0355(5) Uani 1 2 d S . .
C1 C 0.52813(10) 0.55602(8) 0.33683(6) 0.0286(4) Uani 1 1 d . . .
C2 C 0.51014(10) 0.61632(8) 0.30087(6) 0.0268(3) Uani 1 1 d . . .
H2A H 0.5508 0.6557 0.3060 0.032 Uiso 1 1 calc R . .
H2B H 0.5156 0.5990 0.2663 0.032 Uiso 1 1 calc R . .
C3 C 0.39950(10) 0.71180(9) 0.29059(6) 0.0315(4) Uani 1 1 d . . .
H3A H 0.3890 0.7088 0.2544 0.038 Uiso 1 1 calc R . .
H3B H 0.4447 0.7472 0.2964 0.038 Uiso 1 1 calc R . .
C4 C 0.31983(11) 0.73487(9) 0.31744(6) 0.0310(4) Uani 1 1 d . . .
C5 C 0.6147(2) 0.56173(14) 0.48187(11) 0.0816(9) Uani 1 1 d . . .
H5A H 0.6634 0.5576 0.4598 0.122 Uiso 1 1 calc R . .
H5B H 0.5636 0.5672 0.4619 0.122 Uiso 1 1 calc R . .
H5C H 0.6103 0.5185 0.5023 0.122 Uiso 1 1 calc R . .
C6 C 0.70049(17) 0.6171(2) 0.54563(11) 0.0908(10) Uani 1 1 d . . .
H6A H 0.7496 0.6094 0.5244 0.136 Uiso 1 1 calc R . .
H6B H 0.6934 0.5761 0.5679 0.136 Uiso 1 1 calc R . .
H6C H 0.7086 0.6606 0.5654 0.136 Uiso 1 1 calc R . .
H6F H 0.654(5) 0.3750 0.3750 0.18(3) Uiso 1 2 d S . .


_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
V1 O5 1.9691(11) . ?
V1 O5 1.9691(11) 3 ?
V1 N1 1.9956(13) 3 ?
V1 N1 1.9956(13) . ?
V1 O1 2.0569(11) 3 ?
V1 O1 2.0570(11) . ?
V1 O4 2.0656(11) 3 ?
V1 O4 2.0657(11) . ?
O1 C1 1.2729(19) . ?
O2 C1 1.2438(19) . ?
O3 C4 1.237(2) . ?
O4 C4 1.2699(19) . ?
O5 N1 1.3810(17) . ?
O6 H6D 0.837(15) . ?
O6 H6E 0.858(16) . ?
O6 H6F 1.230(10) . ?
N1 C3 1.461(2) . ?
N1 C2 1.461(2) . ?
N2 C6 1.474(3) . ?
N2 C6 1.474(3) 14 ?
N2 C5 1.481(3) . ?
N2 C5 1.481(3) 14 ?
C1 C2 1.514(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.523(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
O5 V1 O5 152.61(8) . 3 ?
O5 V1 N1 151.56(5) . 3 ?
O5 V1 N1 40.76(5) 3 3 ?
O5 V1 N1 40.76(5) . . ?
O5 V1 N1 151.57(5) 3 . ?
N1 V1 N1 150.16(8) 3 . ?
O5 V1 O1 80.10(5) . 3 ?
O5 V1 O1 82.80(5) 3 3 ?
N1 V1 O1 79.25(5) 3 3 ?
N1 V1 O1 120.65(5) . 3 ?
O5 V1 O1 82.80(5) . . ?
O5 V1 O1 80.10(5) 3 . ?
N1 V1 O1 120.65(5) 3 . ?
N1 V1 O1 79.25(5) . . ?
O1 V1 O1 102.21(7) 3 . ?
O5 V1 O4 119.97(5) . 3 ?
O5 V1 O4 81.42(5) 3 3 ?
N1 V1 O4 78.74(5) 3 3 ?
N1 V1 O4 79.29(5) . 3 ?
O1 V1 O4 157.96(4) 3 3 ?
O1 V1 O4 90.13(5) . 3 ?
O5 V1 O4 81.42(5) . . ?
O5 V1 O4 119.97(4) 3 . ?
N1 V1 O4 79.29(5) 3 . ?
N1 V1 O4 78.74(5) . . ?
O1 V1 O4 90.13(5) 3 . ?
O1 V1 O4 157.96(4) . . ?
O4 V1 O4 84.55(6) 3 . ?
C1 O1 V1 116.57(10) . . ?
C4 O4 V1 116.83(10) . . ?
N1 O5 V1 70.65(7) . . ?
H6D O6 H6E 114(2) . . ?
H6D O6 H6F 105(3) . . ?
H6E O6 H6F 105.1(17) . . ?
O5 N1 C3 113.95(12) . . ?
O5 N1 C2 113.51(12) . . ?
C3 N1 C2 119.41(13) . . ?
O5 N1 V1 68.59(7) . . ?
C3 N1 V1 115.57(10) . . ?
C2 N1 V1 115.38(10) . . ?
C6 N2 C6 110.5(3) . 14 ?
C6 N2 C5 110.36(19) . . ?
C6 N2 C5 109.07(19) 14 . ?
C6 N2 C5 109.06(19) . 14 ?
C6 N2 C5 110.36(19) 14 14 ?
C5 N2 C5 107.5(3) . 14 ?
O2 C1 O1 124.44(16) . . ?
O2 C1 C2 118.03(14) . . ?
O1 C1 C2 117.52(13) . . ?
N1 C2 C1 108.39(12) . . ?
N1 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
N1 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
N1 C3 C4 108.38(13) . . ?
N1 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
N1 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
O3 C4 O4 124.08(16) . . ?
O3 C4 C3 118.97(15) . . ?
O4 C4 C3 116.95(14) . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 V1 O1 C1 50.83(11) . . . . ?
O5 V1 O1 C1 -150.65(12) 3 . . . ?
N1 V1 O1 C1 -146.35(11) 3 . . . ?
N1 V1 O1 C1 9.69(11) . . . . ?
O1 V1 O1 C1 129.02(12) 3 . . . ?
O4 V1 O1 C1 -69.38(12) 3 . . . ?
O4 V1 O1 C1 6.3(2) . . . . ?
O5 V1 O4 C4 -54.64(12) . . . . ?
O5 V1 O4 C4 143.64(11) 3 . . . ?
N1 V1 O4 C4 146.36(12) 3 . . . ?
N1 V1 O4 C4 -13.32(12) . . . . ?
O1 V1 O4 C4 -134.60(12) 3 . . . ?
O1 V1 O4 C4 -9.9(2) . . . . ?
O4 V1 O4 C4 66.82(11) 3 . . . ?
O5 V1 O5 N1 -133.52(7) 3 . . . ?
N1 V1 O5 N1 130.36(14) 3 . . . ?
O1 V1 O5 N1 174.32(8) 3 . . . ?
O1 V1 O5 N1 -81.88(8) . . . . ?
O4 V1 O5 N1 4.09(9) 3 . . . ?
O4 V1 O5 N1 82.68(8) . . . . ?
V1 O5 N1 C3 -109.45(11) . . . . ?
V1 O5 N1 C2 109.36(11) . . . . ?
O5 V1 N1 O5 135.52(14) 3 . . . ?
N1 V1 N1 O5 -133.19(7) 3 . . . ?
O1 V1 N1 O5 -6.51(9) 3 . . . ?
O1 V1 N1 O5 91.41(8) . . . . ?
O4 V1 N1 O5 -176.40(8) 3 . . . ?
O4 V1 N1 O5 -89.88(8) . . . . ?
O5 V1 N1 C3 107.20(13) . . . . ?
O5 V1 N1 C3 -117.28(14) 3 . . . ?
N1 V1 N1 C3 -25.98(10) 3 . . . ?
O1 V1 N1 C3 100.70(11) 3 . . . ?
O1 V1 N1 C3 -161.38(11) . . . . ?
O4 V1 N1 C3 -69.19(11) 3 . . . ?
O4 V1 N1 C3 17.32(10) . . . . ?
O5 V1 N1 C2 -106.75(13) . . . . ?
O5 V1 N1 C2 28.77(17) 3 . . . ?
N1 V1 N1 C2 120.06(10) 3 . . . ?
O1 V1 N1 C2 -113.26(10) 3 . . . ?
O1 V1 N1 C2 -15.34(10) . . . . ?
O4 V1 N1 C2 76.85(10) 3 . . . ?
O4 V1 N1 C2 163.37(11) . . . . ?
V1 O1 C1 O2 177.22(13) . . . . ?
V1 O1 C1 C2 -2.11(18) . . . . ?
O5 N1 C2 C1 -58.52(16) . . . . ?
C3 N1 C2 C1 162.60(13) . . . . ?
V1 N1 C2 C1 17.94(15) . . . . ?
O2 C1 C2 N1 170.56(14) . . . . ?
O1 C1 C2 N1 -10.07(19) . . . . ?
O5 N1 C3 C4 58.24(17) . . . . ?
C2 N1 C3 C4 -163.05(13) . . . . ?
V1 N1 C3 C4 -18.45(16) . . . . ?
V1 O4 C4 O3 -173.07(15) . . . . ?
V1 O4 C4 C3 6.54(19) . . . . ?
N1 C3 C4 O3 -172.94(15) . . . . ?
N1 C3 C4 O4 7.4(2) . . . . ?

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
O6 H6D O3 0.837(15) 1.803(16) 2.6364(19) 174(2) 16
O6 H6E O2 0.858(16) 1.742(16) 2.5993(19) 176(2) .
C2 H2A O2 0.99 2.27 3.246(2) 167.0 14
C2 H2B O3 0.99 2.20 3.1748(19) 168.3 22_655
C5 H5A O3 0.98 2.66 3.417(3) 134.6 16
C5 H5C O5 0.98 2.46 3.433(3) 174.4 19_666

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_UMD2266f_a
_database_code_depnum_ccdc_archive 'CCDC 2103586'
loop_
_audit_author_name
_audit_author_address
'James Golen'
;University of Massachusetts Dartmouth
United States of America
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'Tetraethylammonium vanadium(v)-bis-hydroxyiminodiacetate'
_chemical_name_common            TEAVBH
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H28 N3 O10 V'
_chemical_formula_weight         473.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   11.8775(7)
_cell_length_b                   8.1637(5)
_cell_length_c                   12.1364(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.799(2)
_cell_angle_gamma                90
_cell_volume                     1068.28(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      26.39

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.521
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_T_max  0.645
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III photon 200'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34061
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.149
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4351
_reflns_number_gt                4197
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.997

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0375P)²+0.0716P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   'Fourier difference maps'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1898 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.014(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4351
_refine_ls_number_parameters     275
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0215
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0564
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_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
V1 V 0.25782(3) 0.79204(4) 0.62248(3) 0.02370(9) Uani 1 1 d . . . . .
O1 O 0.40065(15) 0.7328(2) 0.77259(14) 0.0360(4) Uani 1 1 d . . . . .
O2 O 0.5644(2) 0.5719(3) 0.8602(2) 0.0609(6) Uani 1 1 d . . . . .
O3 O 0.24343(16) 0.55679(19) 0.59291(16) 0.0334(4) Uani 1 1 d . . . . .
O4 O 0.1332(2) 0.7356(3) 0.26062(17) 0.0630(6) Uani 1 1 d . . . . .
O5 O 0.15601(13) 0.8106(2) 0.44458(12) 0.0326(3) Uani 1 1 d . . . . .
O6 O 0.10781(14) 0.73601(19) 0.64418(14) 0.0313(3) Uani 1 1 d . . . . .
O7 O -0.04909(16) 0.8327(3) 0.67945(16) 0.0468(5) Uani 1 1 d . . . . .
O8 O 0.26829(13) 0.97419(19) 0.73020(13) 0.0298(3) Uani 1 1 d . . . . .
O9 O 0.42019(19) 1.1837(2) 0.5464(2) 0.0564(5) Uani 1 1 d . . . . .
O10 O 0.37624(14) 0.93004(19) 0.58186(15) 0.0317(4) Uani 1 1 d . . . . .
N1 N 0.33273(17) 0.6131(2) 0.56087(17) 0.0296(4) Uani 1 1 d . . . . .
N2 N 0.18483(16) 1.0154(2) 0.61668(16) 0.0274(4) Uani 1 1 d . . . . .
C1 C 0.4792(2) 0.6231(3) 0.7700(2) 0.0378(5) Uani 1 1 d . . . . .
C2 C 0.4595(2) 0.5669(3) 0.6443(2) 0.0379(5) Uani 1 1 d . . . . .
H2A H 0.5191 0.6191 0.6202 0.045 Uiso 1 1 calc R U . . .
H2B H 0.4700 0.4491 0.6433 0.045 Uiso 1 1 calc R U . . .
C3 C 0.2967(2) 0.6134(3) 0.4293(2) 0.0386(5) Uani 1 1 d . . . . .
H3A H 0.2746 0.5035 0.3972 0.046 Uiso 1 1 calc R U . . .
H3B H 0.3654 0.6508 0.4125 0.046 Uiso 1 1 calc R U . . .
C4 C 0.1864(2) 0.7273(3) 0.3702(2) 0.0376(5) Uani 1 1 d . . . . .
C5 C 0.0339(2) 0.8530(3) 0.64749(19) 0.0321(5) Uani 1 1 d . . . . .
C6 C 0.0572(2) 1.0164(3) 0.6030(2) 0.0338(5) Uani 1 1 d . . . . .
H6A H 0.0007 1.0323 0.5185 0.041 Uiso 1 1 calc R U . . .
H6B H 0.0448 1.1045 0.6504 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2282(2) 1.1385(3) 0.5572(2) 0.0362(5) Uani 1 1 d . . . . .
H7A H 0.2369 1.2432 0.5978 0.043 Uiso 1 1 calc R U . . .
H7B H 0.1688 1.1512 0.4734 0.043 Uiso 1 1 calc R U . . .
C8 C 0.3524(2) 1.0841(3) 0.5624(2) 0.0346(5) Uani 1 1 d . . . . .
N3 N 0.7414(2) 0.0448(3) 0.97935(18) 0.0381(5) Uani 1 1 d . . . . .
C9 C 0.8346(3) -0.0232(4) 0.9363(3) 0.0586(8) Uani 1 1 d . . . . .
H9A H 0.8508 0.0597 0.8875 0.070 Uiso 1 1 calc R U . . .
H9B H 0.9118 -0.0433 1.0067 0.070 Uiso 1 1 calc R U . . .
C10 C 0.7967(4) -0.1790(5) 0.8630(4) 0.0858(13) Uani 1 1 d . . . . .
H10A H 0.8558 -0.2043 0.8306 0.129 Uiso 1 1 calc R U . . .
H10B H 0.7161 -0.1648 0.7976 0.129 Uiso 1 1 calc R U . . .
H10C H 0.7939 -0.2672 0.9142 0.129 Uiso 1 1 calc R U . . .
C11 C 0.7025(3) -0.0831(4) 1.0471(3) 0.0525(7) Uani 1 1 d . . . . .
H11A H 0.6439 -0.0334 1.0736 0.063 Uiso 1 1 calc R U . . .
H11B H 0.6596 -0.1705 0.9911 0.063 Uiso 1 1 calc R U . . .
C12 C 0.8066(4) -0.1571(5) 1.1560(3) 0.0764(11) Uani 1 1 d . . . . .
H12A H 0.7733 -0.2353 1.1934 0.115 Uiso 1 1 calc R U . . .
H12B H 0.8490 -0.0722 1.2131 0.115 Uiso 1 1 calc R U . . .
H12C H 0.8637 -0.2108 1.1307 0.115 Uiso 1 1 calc R U . . .
C13 C 0.6267(3) 0.0989(4) 0.8695(2) 0.0529(7) Uani 1 1 d . . . . .
H13A H 0.6518 0.1749 0.8226 0.063 Uiso 1 1 calc R U . . .
H13B H 0.5908 0.0039 0.8188 0.063 Uiso 1 1 calc R U . . .
C14 C 0.5284(3) 0.1791(5) 0.8983(3) 0.0666(9) Uani 1 1 d . . . . .
H14A H 0.4596 0.2096 0.8242 0.100 Uiso 1 1 calc R U . . .
H14B H 0.5620 0.2751 0.9467 0.100 Uiso 1 1 calc R U . . .
H14C H 0.5006 0.1039 0.9425 0.100 Uiso 1 1 calc R U . . .
C15 C 0.7999(3) 0.1889(4) 1.0632(2) 0.0478(6) Uani 1 1 d . . . . .
H15A H 0.7448 0.2221 1.0996 0.057 Uiso 1 1 calc R U . . .
H15B H 0.8767 0.1521 1.1282 0.057 Uiso 1 1 calc R U . . .
C16 C 0.8277(3) 0.3362(4) 1.0048(3) 0.0574(8) Uani 1 1 d . . . . .
H16A H 0.8708 0.4163 1.0659 0.086 Uiso 1 1 calc R U . . .
H16B H 0.7514 0.3822 0.9468 0.086 Uiso 1 1 calc R U . . .
H16C H 0.8785 0.3043 0.9644 0.086 Uiso 1 1 calc R U . . .


_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
V1 O3 1.9480(16) . ?
V1 O8 1.9492(14) . ?
V1 O1 1.9591(16) . ?
V1 O6 1.9613(15) . ?
V1 O5 1.9892(14) . ?
V1 N2 2.0078(18) . ?
V1 N1 2.0109(19) . ?
V1 O10 2.0179(16) . ?
O1 C1 1.304(3) . ?
O2 C1 1.211(3) . ?
O3 N1 1.354(2) . ?
O4 C4 1.211(3) . ?
O5 C4 1.297(3) . ?
O6 C5 1.309(3) . ?
O7 C5 1.213(3) . ?
O8 N2 1.359(2) . ?
O9 C8 1.216(3) . ?
O10 C8 1.289(3) . ?
N1 C2 1.468(3) . ?
N1 C3 1.469(3) . ?
N2 C7 1.452(3) . ?
N2 C6 1.454(3) . ?
C1 C2 1.515(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.519(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.508(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.517(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N3 C9 1.514(3) . ?
N3 C11 1.516(3) . ?
N3 C13 1.519(3) . ?
N3 C15 1.519(4) . ?
C9 C10 1.508(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.506(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.503(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.501(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 V1 O8 148.39(7) . . ?
O3 V1 O1 84.43(7) . . ?
O8 V1 O1 77.16(6) . . ?
O3 V1 O6 77.31(7) . . ?
O8 V1 O6 83.91(6) . . ?
O1 V1 O6 107.38(7) . . ?
O3 V1 O5 84.77(8) . . ?
O8 V1 O5 120.56(7) . . ?
O1 V1 O5 157.41(7) . . ?
O6 V1 O5 89.46(6) . . ?
O3 V1 N2 152.35(8) . . ?
O8 V1 N2 40.15(7) . . ?
O1 V1 N2 116.71(7) . . ?
O6 V1 N2 79.24(7) . . ?
O5 V1 N2 80.54(7) . . ?
O3 V1 N1 39.96(7) . . ?
O8 V1 N1 152.87(7) . . ?
O1 V1 N1 79.68(7) . . ?
O6 V1 N1 116.68(7) . . ?
O5 V1 N1 79.30(7) . . ?
N2 V1 N1 154.01(8) . . ?
O3 V1 O10 121.44(6) . . ?
O8 V1 O10 83.28(6) . . ?
O1 V1 O10 86.82(7) . . ?
O6 V1 O10 158.21(7) . . ?
O5 V1 O10 82.01(7) . . ?
N2 V1 O10 79.59(7) . . ?
N1 V1 O10 81.51(7) . . ?
C1 O1 V1 119.79(15) . . ?
N1 O3 V1 72.52(11) . . ?
C4 O5 V1 119.72(16) . . ?
C5 O6 V1 119.50(14) . . ?
N2 O8 V1 72.24(10) . . ?
C8 O10 V1 117.89(14) . . ?
O3 N1 C2 114.53(19) . . ?
O3 N1 C3 113.97(18) . . ?
C2 N1 C3 119.82(19) . . ?
O3 N1 V1 67.52(10) . . ?
C2 N1 V1 114.57(14) . . ?
C3 N1 V1 115.45(15) . . ?
O8 N2 C7 114.55(18) . . ?
O8 N2 C6 113.53(17) . . ?
C7 N2 C6 120.63(19) . . ?
O8 N2 V1 67.60(10) . . ?
C7 N2 V1 114.09(14) . . ?
C6 N2 V1 115.04(15) . . ?
O2 C1 O1 123.4(2) . . ?
O2 C1 C2 121.5(2) . . ?
O1 C1 C2 115.0(2) . . ?
N1 C2 C1 107.32(19) . . ?
N1 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
N1 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
N1 C3 C4 108.41(18) . . ?
N1 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
N1 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
O4 C4 O5 124.5(2) . . ?
O4 C4 C3 120.2(2) . . ?
O5 C4 C3 115.4(2) . . ?
O7 C5 O6 123.8(2) . . ?
O7 C5 C6 122.1(2) . . ?
O6 C5 C6 114.12(18) . . ?
N2 C6 C5 107.05(19) . . ?
N2 C6 H6A 110.3 . . ?
C5 C6 H6A 110.3 . . ?
N2 C6 H6B 110.3 . . ?
C5 C6 H6B 110.3 . . ?
H6A C6 H6B 108.6 . . ?
N2 C7 C8 108.55(19) . . ?
N2 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
N2 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
O9 C8 O10 125.0(2) . . ?
O9 C8 C7 119.6(2) . . ?
O10 C8 C7 115.4(2) . . ?
C9 N3 C11 111.6(2) . . ?
C9 N3 C13 108.7(2) . . ?
C11 N3 C13 108.1(2) . . ?
C9 N3 C15 108.7(2) . . ?
C11 N3 C15 109.1(2) . . ?
C13 N3 C15 110.7(2) . . ?
C10 C9 N3 115.6(3) . . ?
C10 C9 H9A 108.4 . . ?
N3 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
N3 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N3 115.3(3) . . ?
C12 C11 H11A 108.4 . . ?
N3 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
N3 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N3 114.9(2) . . ?
C14 C13 H13A 108.5 . . ?
N3 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
N3 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N3 115.7(2) . . ?
C16 C15 H15A 108.4 . . ?
N3 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
N3 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C2 H2A O9 0.97 2.47 3.329(3) 147.1 2_646
C2 H2B O9 0.97 2.42 3.309(3) 152.6 1_545
C3 H3B O9 0.97 2.40 3.301(3) 155.0 2_646
C6 H6A O3 0.97 2.64 3.375(3) 132.4 2_556
C6 H6A O6 0.97 2.49 3.335(3) 145.7 2_556
C7 H7A O3 0.97 2.56 3.437(3) 150.0 1_565
C7 H7B O7 0.97 2.33 3.188(3) 146.5 2_556
C9 H9A O4 0.97 2.37 3.330(4) 170.1 2_646
C10 H10A O7 0.96 2.54 3.428(4) 153.1 1_645
C11 H11B O2 0.97 2.59 3.557(4) 173.0 1_545
C14 H14B O2 0.96 2.65 3.293(5) 125.2 .
C16 H16B O2 0.96 2.55 3.458(4) 158.8 .

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.030

_shelxl_version_number           2014/6



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_UMD1830B_a
_database_code_depnum_ccdc_archive 'CCDC 2103587'
loop_
_audit_author_name
_audit_author_address
'James Golen'
;University of Massachusetts Dartmouth
United States of America
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'Trimethylbutylammonium vanadium(iv)-bis-hydroxyiminodiacetate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H48 N4 O12 V'
_chemical_formula_weight         611.58

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.3481(10)
_cell_length_b                   12.7135(10)
_cell_length_c                   18.0999(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.632(2)
_cell_angle_gamma                90
_cell_volume                     3051.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9551
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      25.36

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             1308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.387
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III Cmos'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            82551
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.043
_diffrn_reflns_theta_max         25.442
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5619
_reflns_number_gt                4863
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0265P)²+2.8892P] 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     SHELXL
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5619
_refine_ls_number_parameters     390
_refine_ls_number_restraints     370
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.003
_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
V1 V 0.22381(2) 0.69795(2) 0.71855(2) 0.01786(10) Uani 1 1 d . U . . .
O1 O 0.08348(9) 0.64200(11) 0.67514(8) 0.0285(3) Uani 1 1 d . U . . .
O1W O 0.33328(14) 0.13822(16) 0.68745(14) 0.0639(6) Uani 1 1 d D . . . .
H1WA H 0.362(3) 0.0794(17) 0.676(2) 0.096 Uiso 1 1 d D U . . .
H1WB H 0.377(2) 0.189(2) 0.683(2) 0.096 Uiso 1 1 d D U . . .
O2W O 0.47012(13) 0.29752(12) 0.67446(10) 0.0472(4) Uani 1 1 d D . . . .
H2WA H 0.5217(15) 0.308(2) 0.7073(13) 0.071 Uiso 1 1 d D U . . .
H2WB H 0.447(2) 0.3590(13) 0.6587(16) 0.071 Uiso 1 1 d D U . . .
O2 O -0.04385(12) 0.66378(15) 0.58525(11) 0.0587(5) Uani 1 1 d . U . . .
O3 O 0.15360(9) 0.83277(10) 0.70110(7) 0.0235(3) Uani 1 1 d . U . . .
O4 O 0.41611(12) 0.93570(12) 0.67667(10) 0.0458(4) Uani 1 1 d . U . . .
O5 O 0.35063(9) 0.79316(10) 0.72357(7) 0.0251(3) Uani 1 1 d . U . . .
O6 O 0.28615(9) 0.61564(10) 0.63607(7) 0.0233(3) Uani 1 1 d . U . . .
O7 O 0.39151(11) 0.48628(12) 0.61475(8) 0.0345(3) Uani 1 1 d . U . . .
O8 O 0.22587(9) 0.55792(10) 0.76339(7) 0.0252(3) Uani 1 1 d . U . . .
O9 O 0.26043(12) 0.71906(12) 0.94569(8) 0.0390(4) Uani 1 1 d . U . . .
O10 O 0.20754(10) 0.74268(11) 0.82574(7) 0.0277(3) Uani 1 1 d . U . . .
N1 N 0.18568(11) 0.79899(12) 0.63507(8) 0.0192(3) Uani 1 1 d . U . . .
N2 N 0.32090(11) 0.60178(12) 0.77863(8) 0.0216(3) Uani 1 1 d . U . . .
N3 N 0.10155(13) 0.29622(13) 0.68100(10) 0.0306(4) Uani 1 1 d . U . . .
N4 N 0.71895(12) 0.52119(13) 0.58546(10) 0.0306(4) Uani 1 1 d . U . . .
C1 C 0.04108(14) 0.68480(16) 0.61564(12) 0.0308(4) Uani 1 1 d . U . . .
C2 C 0.10296(14) 0.76675(15) 0.58002(10) 0.0248(4) Uani 1 1 d . U . . .
H2A H 0.1298 0.7367 0.5358 0.030 Uiso 1 1 calc R U . . .
H2B H 0.0603 0.8282 0.5639 0.030 Uiso 1 1 calc R U . . .
C3 C 0.26554(14) 0.86578(15) 0.61245(10) 0.0256(4) Uani 1 1 d . U . . .
H3A H 0.2399 0.9380 0.6023 0.031 Uiso 1 1 calc R U . . .
H3B H 0.2896 0.8378 0.5666 0.031 Uiso 1 1 calc R U . . .
C4 C 0.35113(14) 0.86687(15) 0.67541(11) 0.0265(4) Uani 1 1 d . U . . .
C5 C 0.35490(13) 0.54896(15) 0.65655(10) 0.0235(4) Uani 1 1 d . U . . .
C6 C 0.39479(14) 0.54940(16) 0.73863(10) 0.0277(4) Uani 1 1 d . U . . .
H6A H 0.4055 0.4764 0.7569 0.033 Uiso 1 1 calc R U . . .
H6B H 0.4600 0.5872 0.7464 0.033 Uiso 1 1 calc R U . . .
C7 C 0.34495(15) 0.62626(16) 0.85737(10) 0.0275(4) Uani 1 1 d . U . . .
H7A H 0.4122 0.6597 0.8663 0.033 Uiso 1 1 calc R U . . .
H7B H 0.3459 0.5610 0.8873 0.033 Uiso 1 1 calc R U . . .
C8 C 0.26460(15) 0.70078(15) 0.87936(10) 0.0262(4) Uani 1 1 d . U . . .
C9 C 0.06818(16) 0.18227(16) 0.68148(11) 0.0303(4) Uani 1 1 d . U . . .
H9A H 0.1293 0.1375 0.6876 0.036 Uiso 1 1 calc R U . . .
H9B H 0.0322 0.1712 0.7257 0.036 Uiso 1 1 calc R U . . .
C10 C 0.00107(16) 0.14410(16) 0.61403(11) 0.0307(4) Uani 1 1 d . U . . .
H10A H 0.0381 0.1463 0.5697 0.037 Uiso 1 1 calc R U . . .
H10B H -0.0589 0.1901 0.6047 0.037 Uiso 1 1 calc R U . . .
C11 C -0.03158(17) 0.03170(17) 0.62815(13) 0.0361(5) Uani 1 1 d . U . . .
H11A H 0.0290 -0.0138 0.6346 0.043 Uiso 1 1 calc R U . . .
H11B H -0.0627 0.0299 0.6752 0.043 Uiso 1 1 calc R U . . .
C12 C -0.10593(17) -0.01304(19) 0.56623(14) 0.0438(6) Uani 1 1 d . U . . .
H12A H -0.1208 -0.0864 0.5775 0.066 Uiso 1 1 calc R U . . .
H12B H -0.0766 -0.0097 0.5191 0.066 Uiso 1 1 calc R U . . .
H12C H -0.1684 0.0282 0.5621 0.066 Uiso 1 1 calc R U . . .
C13 C 0.01363(18) 0.36916(18) 0.67882(16) 0.0474(6) Uani 1 1 d . U . . .
H13A H -0.0248 0.3535 0.7205 0.071 Uiso 1 1 calc R U . . .
H13B H -0.0298 0.3599 0.6318 0.071 Uiso 1 1 calc R U . . .
H13C H 0.0378 0.4419 0.6828 0.071 Uiso 1 1 calc R U . . .
C14 C 0.15961(18) 0.3185(2) 0.61731(14) 0.0467(6) Uani 1 1 d . U . . .
H14A H 0.2144 0.2673 0.6170 0.070 Uiso 1 1 calc R U . . .
H14B H 0.1879 0.3896 0.6223 0.070 Uiso 1 1 calc R U . . .
H14C H 0.1147 0.3133 0.5706 0.070 Uiso 1 1 calc R U . . .
C15 C 0.1693(2) 0.3137(2) 0.75212(14) 0.0480(6) Uani 1 1 d . U . . .
H15A H 0.1329 0.2962 0.7945 0.072 Uiso 1 1 calc R U . . .
H15B H 0.1902 0.3876 0.7554 0.072 Uiso 1 1 calc R U . . .
H15C H 0.2290 0.2686 0.7528 0.072 Uiso 1 1 calc R U . . .
C16 C 0.69879(18) 0.63322(18) 0.56026(15) 0.0450(6) Uani 1 1 d D U . . .
H16A H 0.6699 0.6331 0.5073 0.054 Uiso 0.478(12) 1 calc R U P A 1
H16B H 0.7634 0.6721 0.5640 0.054 Uiso 0.478(12) 1 calc R U P A 1
H16C H 0.6876 0.6328 0.5052 0.054 Uiso 0.522(12) 1 calc R U P A 2
H16D H 0.7612 0.6740 0.5746 0.054 Uiso 0.522(12) 1 calc R U P A 2
C17 C 0.6256(7) 0.6907(8) 0.6066(5) 0.0359(17) Uani 0.478(12) 1 d D U P A 1
H17A H 0.5600 0.6537 0.5999 0.043 Uiso 0.478(12) 1 calc R U P A 1
H17B H 0.6524 0.6851 0.6598 0.043 Uiso 0.478(12) 1 calc R U P A 1
C18 C 0.6072(15) 0.8071(11) 0.5879(7) 0.077(2) Uani 0.478(12) 1 d D U P A 1
H18A H 0.5417 0.8274 0.6045 0.093 Uiso 0.478(12) 1 calc R U P A 1
H18B H 0.6601 0.8488 0.6176 0.093 Uiso 0.478(12) 1 calc R U P A 1
C19 C 0.6058(12) 0.8384(12) 0.5078(6) 0.101(3) Uani 0.478(12) 1 d D U P A 1
H19A H 0.5905 0.9136 0.5024 0.152 Uiso 0.478(12) 1 calc R U P A 1
H19B H 0.5541 0.7977 0.4773 0.152 Uiso 0.478(12) 1 calc R U P A 1
H19C H 0.6720 0.8243 0.4914 0.152 Uiso 0.478(12) 1 calc R U P A 1
C17A C 0.6139(9) 0.6924(10) 0.5871(8) 0.083(4) Uani 0.522(12) 1 d D U P A 2
H17C H 0.6094 0.6740 0.6397 0.100 Uiso 0.522(12) 1 calc R U P A 2
H17D H 0.5500 0.6711 0.5577 0.100 Uiso 0.522(12) 1 calc R U P A 2
C18A C 0.6270(12) 0.8121(10) 0.5806(8) 0.077(2) Uani 0.522(12) 1 d D U P A 2
H18C H 0.6120 0.8492 0.6261 0.093 Uiso 0.522(12) 1 calc R U P A 2
H18D H 0.6956 0.8310 0.5694 0.093 Uiso 0.522(12) 1 calc R U P A 2
C19A C 0.5488(10) 0.8337(11) 0.5159(6) 0.101(3) Uani 0.522(12) 1 d D U P A 2
H19D H 0.5320 0.9087 0.5146 0.152 Uiso 0.522(12) 1 calc R U P A 2
H19E H 0.4881 0.7924 0.5213 0.152 Uiso 0.522(12) 1 calc R U P A 2
H19F H 0.5753 0.8140 0.4695 0.152 Uiso 0.522(12) 1 calc R U P A 2
C20 C 0.62366(18) 0.4581(2) 0.57425(18) 0.0552(7) Uani 1 1 d . U . . .
H20A H 0.5762 0.4844 0.6074 0.083 Uiso 1 1 calc R U . . .
H20B H 0.6389 0.3840 0.5856 0.083 Uiso 1 1 calc R U . . .
H20C H 0.5935 0.4646 0.5225 0.083 Uiso 1 1 calc R U . . .
C21 C 0.7656(2) 0.5169(2) 0.66439(12) 0.0506(7) Uani 1 1 d . U . . .
H21A H 0.7188 0.5468 0.6967 0.076 Uiso 1 1 calc R U . . .
H21B H 0.8284 0.5575 0.6698 0.076 Uiso 1 1 calc R U . . .
H21C H 0.7801 0.4436 0.6786 0.076 Uiso 1 1 calc R U . . .
C22 C 0.79159(16) 0.47405(19) 0.53832(12) 0.0369(5) Uani 1 1 d . U . . .
H22A H 0.7623 0.4751 0.4861 0.055 Uiso 1 1 calc R U . . .
H22B H 0.8059 0.4013 0.5539 0.055 Uiso 1 1 calc R U . . .
H22C H 0.8543 0.5148 0.5439 0.055 Uiso 1 1 calc R U . . .


_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
V1 O8 1.9553(13) . ?
V1 O3 1.9616(13) . ?
V1 N1 2.0037(15) . ?
V1 N2 2.0079(15) . ?
V1 O10 2.0573(13) . ?
V1 O1 2.0717(13) . ?
V1 O5 2.0745(13) . ?
V1 O6 2.0743(13) . ?
O1 C1 1.279(2) . ?
O1W H1WA 0.877(10) . ?
O1W H1WB 0.875(10) . ?
O2W H2WA 0.867(10) . ?
O2W H2WB 0.877(10) . ?
O2 C1 1.231(2) . ?
O3 N1 1.3837(18) . ?
O4 C4 1.230(2) . ?
O5 C4 1.280(2) . ?
O6 C5 1.273(2) . ?
O7 C5 1.238(2) . ?
O8 N2 1.384(2) . ?
O9 C8 1.230(2) . ?
O10 C8 1.279(2) . ?
N1 C2 1.458(2) . ?
N1 C3 1.458(2) . ?
N2 C6 1.451(2) . ?
N2 C7 1.458(2) . ?
N3 C14 1.489(3) . ?
N3 C13 1.493(3) . ?
N3 C15 1.502(3) . ?
N3 C9 1.516(3) . ?
N4 C22 1.489(3) . ?
N4 C21 1.492(3) . ?
N4 C20 1.498(3) . ?
N4 C16 1.510(3) . ?
C1 C2 1.519(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.518(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.519(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.518(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C10 1.509(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.524(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.519(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17A 1.487(8) . ?
C16 C17 1.543(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 H16C 0.9900 . ?
C16 H16D 0.9900 . ?
C17 C18 1.532(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.503(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C17A C18A 1.538(8) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A C19A 1.501(9) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
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
O8 V1 O3 147.77(6) . . ?
O8 V1 N1 152.48(6) . . ?
O3 V1 N1 40.83(5) . . ?
O8 V1 N2 40.85(6) . . ?
O3 V1 N2 152.35(6) . . ?
N1 V1 N2 152.96(6) . . ?
O8 V1 O10 81.85(5) . . ?
O3 V1 O10 79.03(5) . . ?
N1 V1 O10 119.25(6) . . ?
N2 V1 O10 77.84(6) . . ?
O8 V1 O1 79.25(5) . . ?
O3 V1 O1 81.06(5) . . ?
N1 V1 O1 78.13(6) . . ?
N2 V1 O1 119.68(6) . . ?
O10 V1 O1 105.26(6) . . ?
O8 V1 O5 122.74(5) . . ?
O3 V1 O5 82.50(5) . . ?
N1 V1 O5 78.10(5) . . ?
N2 V1 O5 81.91(6) . . ?
O10 V1 O5 88.39(5) . . ?
O1 V1 O5 156.13(5) . . ?
O8 V1 O6 81.48(5) . . ?
O3 V1 O6 123.29(5) . . ?
N1 V1 O6 82.46(5) . . ?
N2 V1 O6 78.18(6) . . ?
O10 V1 O6 155.92(5) . . ?
O1 V1 O6 88.52(5) . . ?
O5 V1 O6 86.14(5) . . ?
C1 O1 V1 117.78(12) . . ?
H1WA O1W H1WB 107(3) . . ?
H2WA O2W H2WB 108(3) . . ?
N1 O3 V1 71.22(8) . . ?
C4 O5 V1 117.75(11) . . ?
C5 O6 V1 117.52(11) . . ?
N2 O8 V1 71.62(8) . . ?
C8 O10 V1 118.82(12) . . ?
O3 N1 C2 113.08(13) . . ?
O3 N1 C3 111.78(14) . . ?
C2 N1 C3 119.49(14) . . ?
O3 N1 V1 67.95(8) . . ?
C2 N1 V1 116.20(12) . . ?
C3 N1 V1 117.06(11) . . ?
O8 N2 C6 112.08(14) . . ?
O8 N2 C7 111.97(14) . . ?
C6 N2 C7 120.02(15) . . ?
O8 N2 V1 67.53(8) . . ?
C6 N2 V1 116.27(11) . . ?
C7 N2 V1 117.06(12) . . ?
C14 N3 C13 109.84(18) . . ?
C14 N3 C15 108.65(18) . . ?
C13 N3 C15 108.95(19) . . ?
C14 N3 C9 111.47(17) . . ?
C13 N3 C9 111.30(16) . . ?
C15 N3 C9 106.52(16) . . ?
C22 N4 C21 107.86(17) . . ?
C22 N4 C20 107.80(18) . . ?
C21 N4 C20 111.3(2) . . ?
C22 N4 C16 108.15(17) . . ?
C21 N4 C16 111.33(18) . . ?
C20 N4 C16 110.20(17) . . ?
O2 C1 O1 125.4(2) . . ?
O2 C1 C2 118.50(19) . . ?
O1 C1 C2 116.10(16) . . ?
N1 C2 C1 107.98(15) . . ?
N1 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
N1 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
N1 C3 C4 107.81(15) . . ?
N1 C3 H3A 110.1 . . ?
C4 C3 H3A 110.1 . . ?
N1 C3 H3B 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.5 . . ?
O4 C4 O5 124.53(18) . . ?
O4 C4 C3 119.24(18) . . ?
O5 C4 C3 116.22(16) . . ?
O7 C5 O6 124.97(17) . . ?
O7 C5 C6 118.79(17) . . ?
O6 C5 C6 116.23(16) . . ?
N2 C6 C5 107.94(15) . . ?
N2 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
N2 C6 H6B 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
N2 C7 C8 107.88(15) . . ?
N2 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
N2 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
O9 C8 O10 124.87(19) . . ?
O9 C8 C7 119.11(18) . . ?
O10 C8 C7 115.97(16) . . ?
C10 C9 N3 116.75(17) . . ?
C10 C9 H9A 108.1 . . ?
N3 C9 H9A 108.1 . . ?
C10 C9 H9B 108.1 . . ?
N3 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
C9 C10 C11 108.70(17) . . ?
C9 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 C10 113.74(19) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 C17A 119.6(6) . . ?
N4 C16 C17 112.6(4) . . ?
N4 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
N4 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
N4 C16 H16C 107.4 . . ?
C17A C16 H16C 107.4 . . ?
N4 C16 H16D 107.4 . . ?
C17A C16 H16D 107.4 . . ?
H16C C16 H16D 106.9 . . ?
C18 C17 C16 115.7(9) . . ?
C18 C17 H17A 108.4 . . ?
C16 C17 H17A 108.4 . . ?
C18 C17 H17B 108.4 . . ?
C16 C17 H17B 108.4 . . ?
H17A C17 H17B 107.4 . . ?
C19 C18 C17 116.9(13) . . ?
C19 C18 H18A 108.1 . . ?
C17 C18 H18A 108.1 . . ?
C19 C18 H18B 108.1 . . ?
C17 C18 H18B 108.1 . . ?
H18A C18 H18B 107.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C17A C18A 112.2(11) . . ?
C16 C17A H17C 109.2 . . ?
C18A C17A H17C 109.2 . . ?
C16 C17A H17D 109.2 . . ?
C18A C17A H17D 109.2 . . ?
H17C C17A H17D 107.9 . . ?
C19A C18A C17A 99.6(11) . . ?
C19A C18A H18C 111.9 . . ?
C17A C18A H18C 111.9 . . ?
C19A C18A H18D 111.9 . . ?
C17A C18A H18D 111.9 . . ?
H18C C18A H18D 109.6 . . ?
C18A C19A H19D 109.5 . . ?
C18A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C18A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
N4 C20 H20A 109.5 . . ?
N4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
V1 O3 N1 C2 110.20(13) . . . . ?
V1 O3 N1 C3 -111.51(13) . . . . ?
V1 O8 N2 C6 -110.43(13) . . . . ?
V1 O8 N2 C7 111.34(13) . . . . ?
V1 O1 C1 O2 -176.35(19) . . . . ?
V1 O1 C1 C2 4.7(2) . . . . ?
O3 N1 C2 C1 -54.14(19) . . . . ?
C3 N1 C2 C1 171.08(16) . . . . ?
V1 N1 C2 C1 21.67(18) . . . . ?
O2 C1 C2 N1 164.3(2) . . . . ?
O1 C1 C2 N1 -16.6(2) . . . . ?
O3 N1 C3 C4 56.84(19) . . . . ?
C2 N1 C3 C4 -167.85(15) . . . . ?
V1 N1 C3 C4 -18.70(19) . . . . ?
V1 O5 C4 O4 171.88(17) . . . . ?
V1 O5 C4 C3 -9.2(2) . . . . ?
N1 C3 C4 O4 -163.42(18) . . . . ?
N1 C3 C4 O5 17.6(2) . . . . ?
V1 O6 C5 O7 171.91(15) . . . . ?
V1 O6 C5 C6 -9.2(2) . . . . ?
O8 N2 C6 C5 53.7(2) . . . . ?
C7 N2 C6 C5 -171.82(16) . . . . ?
V1 N2 C6 C5 -21.3(2) . . . . ?
O7 C5 C6 N2 -161.65(17) . . . . ?
O6 C5 C6 N2 19.4(2) . . . . ?
O8 N2 C7 C8 -57.80(19) . . . . ?
C6 N2 C7 C8 167.68(16) . . . . ?
V1 N2 C7 C8 17.33(19) . . . . ?
V1 O10 C8 O9 -178.12(16) . . . . ?
V1 O10 C8 C7 4.1(2) . . . . ?
N2 C7 C8 O9 168.63(17) . . . . ?
N2 C7 C8 O10 -13.5(2) . . . . ?
C14 N3 C9 C10 -59.9(2) . . . . ?
C13 N3 C9 C10 63.1(2) . . . . ?
C15 N3 C9 C10 -178.29(19) . . . . ?
N3 C9 C10 C11 -174.96(17) . . . . ?
C9 C10 C11 C12 175.79(18) . . . . ?
C22 N4 C16 C17A 167.8(7) . . . . ?
C21 N4 C16 C17A -73.9(7) . . . . ?
C20 N4 C16 C17A 50.2(7) . . . . ?
C22 N4 C16 C17 -178.9(5) . . . . ?
C21 N4 C16 C17 -60.5(5) . . . . ?
C20 N4 C16 C17 63.5(5) . . . . ?
N4 C16 C17 C18 175.9(9) . . . . ?
C16 C17 C18 C19 35(2) . . . . ?
N4 C16 C17A C18A 159.1(7) . . . . ?
C16 C17A C18A C19A 106.7(15) . . . . ?

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
C2 H2A O9 0.99 2.58 3.397(2) 139.5 4_575
C3 H3B O9 0.99 2.29 3.198(2) 151.3 4_575
C6 H6A O4 0.99 2.59 3.149(2) 115.6 2_646
C7 H7A O2W 0.99 2.52 3.390(3) 146.7 2_656
C9 H9B O1 0.99 2.53 3.508(2) 171.3 2_546
C10 H10B O10 0.99 2.56 3.349(2) 136.7 2_546
C13 H13A O3 0.98 2.37 3.323(3) 164.8 2_546
C13 H13C O1 0.98 2.62 3.595(3) 171.3 .
C14 H14A O1W 0.98 2.52 3.400(3) 148.8 .
C15 H15C O1W 0.98 2.54 3.425(3) 149.6 .
C15 H15B O8 0.98 2.22 3.197(3) 175.8 .
C20 H20A O7 0.98 2.48 3.285(3) 138.8 .
C20 H20C O7 0.98 2.59 3.476(3) 150.3 3_666
C20 H20B O9 0.98 2.59 3.448(3) 146.4 2_646
C21 H21A O1W 0.98 2.56 3.483(3) 156.3 2_656
C21 H21C O3 0.98 2.66 3.459(3) 139.1 2_646
C21 H21C O10 0.98 2.56 3.507(3) 162.2 2_646
C22 H22A O6 0.98 2.51 3.403(2) 151.2 3_666
C22 H22A O7 0.98 2.63 3.513(3) 149.8 3_666
C22 H22C O2 0.98 2.40 3.307(3) 153.6 1_655
C22 H22B O9 0.98 2.48 3.335(3) 145.6 2_646
O2W H2WA O5 0.867(10) 2.003(13) 2.849(2) 165(3) 2_646
O2W H2WB O7 0.877(10) 1.913(11) 2.787(2) 174(3) .
O1W H1WA O4 0.877(10) 1.964(14) 2.818(3) 164(4) 1_545
O1W H1WB O2W 0.875(10) 1.880(10) 2.755(3) 180(4) .

_refine_diff_density_max         0.752
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.048

_shelxl_version_number           2014/6



