# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ARC_CCOM_sb
_audit_block_doi                 10.5517/cc11pz3t
_database_code_depnum_ccdc_archive 'CCDC 974426'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C4CC02093F 2014
_audit_update_record             
;
2013-11-29 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H27 Cl N4 O9 V'
_chemical_formula_sum            'C26 H27 Cl N4 O9 V'
_chemical_formula_weight         625.91

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'
Cl Cl 0.1484 0.1585 '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           Triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4205(5)
_cell_length_b                   11.9369(11)
_cell_length_c                   13.5029(11)
_cell_angle_alpha                68.758(8)
_cell_angle_beta                 77.535(5)
_cell_angle_gamma                84.902(6)
_cell_volume                     1381.80(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             646
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7471
_exptl_absorpt_correction_T_max  0.9038
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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 Smart CCD Area Detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19241
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0561
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         27.47
_reflns_number_total             6319
_reflns_number_gt                4427
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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 > 2σ(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)+(0.0503P)²+0.8166P] 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         6319
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.42269(5) 0.13967(4) 0.78312(4) 0.03689(16) Uani 1 1 d . . .
Cl1 Cl 0.85479(9) 0.46086(8) 0.77288(6) 0.0537(2) Uani 1 1 d . . .
O1 O 0.3051(2) 0.05166(19) 0.87593(16) 0.0524(6) Uani 1 1 d . . .
O2 O 0.3838(2) 0.28311(19) 0.82313(17) 0.0479(5) Uani 1 1 d . . .
O3 O 0.5342(2) 0.02707(18) 0.71675(16) 0.0453(5) Uani 1 1 d . . .
O4 O 0.7176(4) 0.2953(3) 1.1583(2) 0.0838(10) Uani 1 1 d . . .
O5 O 0.8768(4) 0.3364(3) 0.7950(3) 0.1006(10) Uani 1 1 d . . .
O6 O 0.8710(4) 0.4818(3) 0.8673(3) 0.1036(11) Uani 1 1 d . . .
O7 O 0.9541(4) 0.5261(4) 0.6834(3) 0.1409(17) Uani 1 1 d . . .
O8 O 0.7085(3) 0.4940(3) 0.7577(2) 0.0792(8) Uani 1 1 d . . .
O9 O 0.6127(4) 0.1179(3) 0.3459(2) 0.1023(12) Uani 1 1 d . . .
H9A H 0.5366 0.0846 0.3536 0.154 Uiso 1 1 calc R . .
N1 N 0.5437(2) 0.2788(2) 0.62375(18) 0.0369(5) Uani 1 1 d . . .
N2 N 0.2821(3) 0.1913(2) 0.66909(19) 0.0388(6) Uani 1 1 d . . .
N3 N 0.6040(3) 0.1099(2) 0.85571(18) 0.0378(6) Uani 1 1 d . . .
N4 N 0.3498(4) 0.3939(3) 1.0360(2) 0.0558(8) Uani 1 1 d . . .
C1 C 0.6741(3) 0.3250(3) 0.6088(3) 0.0450(7) Uani 1 1 d . . .
H1 H 0.7203 0.3032 0.6675 0.054 Uiso 1 1 calc R . .
C2 C 0.7433(4) 0.4036(3) 0.5103(3) 0.0529(8) Uani 1 1 d . . .
H2 H 0.8337 0.4346 0.5028 0.064 Uiso 1 1 calc R . .
C3 C 0.6756(4) 0.4346(3) 0.4238(3) 0.0563(9) Uani 1 1 d . . .
H3 H 0.7205 0.4865 0.3562 0.068 Uiso 1 1 calc R . .
C4 C 0.5405(4) 0.3887(3) 0.4374(2) 0.0498(8) Uani 1 1 d . . .
H4 H 0.4933 0.4091 0.3793 0.060 Uiso 1 1 calc R . .
C5 C 0.4762(3) 0.3113(2) 0.5393(2) 0.0376(6) Uani 1 1 d . . .
C6 C 0.3282(3) 0.2623(2) 0.5647(2) 0.0382(6) Uani 1 1 d . . .
C7 C 0.2405(4) 0.2884(3) 0.4894(3) 0.0526(8) Uani 1 1 d . . .
H7 H 0.2741 0.3369 0.4178 0.063 Uiso 1 1 calc R . .
C8 C 0.1018(4) 0.2416(3) 0.5217(3) 0.0613(10) Uani 1 1 d . . .
H8 H 0.0415 0.2584 0.4718 0.074 Uiso 1 1 calc R . .
C9 C 0.0543(4) 0.1711(3) 0.6266(3) 0.0599(10) Uani 1 1 d . . .
H9 H -0.0386 0.1390 0.6495 0.072 Uiso 1 1 calc R . .
C10 C 0.1457(3) 0.1484(3) 0.6977(3) 0.0523(8) Uani 1 1 d . . .
H10 H 0.1123 0.1008 0.7696 0.063 Uiso 1 1 calc R . .
C11 C 0.6524(3) -0.0215(3) 0.7566(2) 0.0431(7) Uani 1 1 d . . .
C12 C 0.7329(4) -0.1138(3) 0.7279(3) 0.0548(9) Uani 1 1 d . . .
H12 H 0.7048 -0.1420 0.6793 0.066 Uiso 1 1 calc R . .
C13 C 0.8530(4) -0.1625(3) 0.7716(3) 0.0638(10) Uani 1 1 d . . .
H13 H 0.9055 -0.2237 0.7523 0.077 Uiso 1 1 calc R . .
C14 C 0.8966(4) -0.1217(3) 0.8434(3) 0.0642(10) Uani 1 1 d . . .
H14 H 0.9784 -0.1555 0.8720 0.077 Uiso 1 1 calc R . .
C15 C 0.8199(4) -0.0310(3) 0.8734(3) 0.0540(9) Uani 1 1 d . . .
H15 H 0.8498 -0.0039 0.9221 0.065 Uiso 1 1 calc R . .
C16 C 0.6972(3) 0.0199(3) 0.8302(2) 0.0408(7) Uani 1 1 d . . .
C17 C 0.6298(3) 0.1608(3) 0.9196(2) 0.0419(7) Uani 1 1 d . . .
H17 H 0.7160 0.1400 0.9453 0.050 Uiso 1 1 calc R . .
C18 C 0.5357(3) 0.2472(3) 0.9541(2) 0.0412(7) Uani 1 1 d . . .
C19 C 0.4143(3) 0.2980(3) 0.9074(2) 0.0413(7) Uani 1 1 d . . .
C20 C 0.3165(4) 0.3714(3) 0.9536(3) 0.0469(8) Uani 1 1 d . . .
C21 C 0.1790(4) 0.4195(3) 0.9168(3) 0.0638(10) Uani 1 1 d . . .
H21A H 0.1289 0.4664 0.9586 0.096 Uiso 1 1 calc R . .
H21B H 0.1188 0.3540 0.9265 0.096 Uiso 1 1 calc R . .
H21C H 0.2001 0.4692 0.8415 0.096 Uiso 1 1 calc R . .
C22 C 0.4702(4) 0.3543(3) 1.0771(3) 0.0549(9) Uani 1 1 d . . .
H22 H 0.4875 0.3769 1.1325 0.066 Uiso 1 1 calc R . .
C23 C 0.5667(4) 0.2815(3) 1.0380(2) 0.0471(8) Uani 1 1 d . . .
C24 C 0.7035(4) 0.2403(3) 1.0843(3) 0.0628(10) Uani 1 1 d . . .
H24A H 0.7013 0.1537 1.1207 0.075 Uiso 1 1 calc R . .
H24B H 0.7877 0.2592 1.0254 0.075 Uiso 1 1 calc R . .
C25 C 0.8041(5) 0.1181(4) 0.4352(4) 0.0869(14) Uani 1 1 d . . .
H25A H 0.8358 0.0769 0.5024 0.130 Uiso 1 1 calc R . .
H25B H 0.7894 0.2018 0.4251 0.130 Uiso 1 1 calc R . .
H25C H 0.8767 0.1094 0.3764 0.130 Uiso 1 1 calc R . .
C26 C 0.6692(5) 0.0672(4) 0.4378(4) 0.0793(12) Uani 1 1 d . . .
H26A H 0.6849 -0.0180 0.4508 0.095 Uiso 1 1 calc R . .
H26B H 0.5978 0.0748 0.4986 0.095 Uiso 1 1 calc R . .
H4A H 0.291(4) 0.433(3) 1.063(3) 0.055(12) Uiso 1 1 d . . .
H4B H 0.682(6) 0.245(5) 1.228(4) 0.13(2) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.598(2) . ?
V1 O2 1.957(2) . ?
V1 O3 1.982(2) . ?
V1 N3 2.089(2) . ?
V1 N2 2.134(2) . ?
V1 N1 2.319(2) . ?
Cl1 O7 1.379(3) . ?
Cl1 O5 1.411(3) . ?
Cl1 O6 1.426(3) . ?
Cl1 O8 1.437(3) . ?
O2 C19 1.306(3) . ?
O3 C11 1.336(4) . ?
O4 C24 1.412(4) . ?
O4 H4B 0.92(5) . ?
O9 C26 1.369(4) . ?
O9 H9A 0.8200 . ?
N1 C1 1.336(4) . ?
N1 C5 1.344(3) . ?
N2 C10 1.349(4) . ?
N2 C6 1.353(3) . ?
N3 C17 1.292(4) . ?
N3 C16 1.419(4) . ?
N4 C20 1.338(4) . ?
N4 C22 1.343(5) . ?
N4 H4A 0.80(3) . ?
C1 C2 1.381(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.482(4) . ?
C6 C7 1.378(4) . ?
C7 C8 1.384(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.358(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.366(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.405(4) . ?
C11 C16 1.409(4) . ?
C12 C13 1.374(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.399(4) . ?
C15 H15 0.9300 . ?
C17 C18 1.439(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.409(4) . ?
C18 C23 1.427(4) . ?
C19 C20 1.417(4) . ?
C20 C21 1.482(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.358(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.519(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.445(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 99.32(11) . . ?
O1 V1 O3 101.12(11) . . ?
O2 V1 O3 157.83(9) . . ?
O1 V1 N3 102.47(10) . . ?
O2 V1 N3 86.82(9) . . ?
O3 V1 N3 80.48(9) . . ?
O1 V1 N2 92.88(10) . . ?
O2 V1 N2 95.20(9) . . ?
O3 V1 N2 92.28(9) . . ?
N3 V1 N2 164.00(9) . . ?
O1 V1 N1 164.91(10) . . ?
O2 V1 N1 81.43(9) . . ?
O3 V1 N1 81.08(8) . . ?
N3 V1 N1 92.62(8) . . ?
N2 V1 N1 72.07(8) . . ?
O7 Cl1 O5 110.8(3) . . ?
O7 Cl1 O6 111.0(3) . . ?
O5 Cl1 O6 106.4(2) . . ?
O7 Cl1 O8 110.97(19) . . ?
O5 Cl1 O8 109.90(19) . . ?
O6 Cl1 O8 107.64(18) . . ?
C19 O2 V1 126.92(19) . . ?
C11 O3 V1 114.84(19) . . ?
C24 O4 H4B 109(3) . . ?
C26 O9 H9A 109.5 . . ?
C1 N1 C5 118.5(2) . . ?
C1 N1 V1 125.9(2) . . ?
C5 N1 V1 115.57(18) . . ?
C10 N2 C6 117.6(2) . . ?
C10 N2 V1 120.7(2) . . ?
C6 N2 V1 121.62(19) . . ?
C17 N3 C16 122.2(3) . . ?
C17 N3 V1 126.5(2) . . ?
C16 N3 V1 111.24(18) . . ?
C20 N4 C22 125.1(3) . . ?
C20 N4 H4A 116(3) . . ?
C22 N4 H4A 119(3) . . ?
N1 C1 C2 123.0(3) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.5(3) . . ?
N1 C5 C6 115.0(2) . . ?
C4 C5 C6 123.5(3) . . ?
N2 C6 C7 121.5(3) . . ?
N2 C6 C5 115.1(2) . . ?
C7 C6 C5 123.4(3) . . ?
C6 C7 C8 119.2(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 118.6(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
N2 C10 C9 123.4(3) . . ?
N2 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
O3 C11 C12 121.8(3) . . ?
O3 C11 C16 119.3(3) . . ?
C12 C11 C16 118.9(3) . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 119.6(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C11 119.9(3) . . ?
C15 C16 N3 126.6(3) . . ?
C11 C16 N3 113.5(3) . . ?
N3 C17 C18 125.2(3) . . ?
N3 C17 H17 117.4 . . ?
C18 C17 H17 117.4 . . ?
C19 C18 C23 119.5(3) . . ?
C19 C18 C17 121.6(3) . . ?
C23 C18 C17 118.9(3) . . ?
O2 C19 C18 124.9(3) . . ?
O2 C19 C20 116.4(3) . . ?
C18 C19 C20 118.8(3) . . ?
N4 C20 C19 117.6(3) . . ?
N4 C20 C21 119.7(3) . . ?
C19 C20 C21 122.7(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 C23 120.2(3) . . ?
N4 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 118.5(3) . . ?
C22 C23 C24 119.1(3) . . ?
C18 C23 C24 122.4(3) . . ?
O4 C24 C23 112.1(3) . . ?
O4 C24 H24A 109.2 . . ?
C23 C24 H24A 109.2 . . ?
O4 C24 H24B 109.2 . . ?
C23 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O9 C26 C25 115.2(4) . . ?
O9 C26 H26A 108.5 . . ?
C25 C26 H26A 108.5 . . ?
O9 C26 H26B 108.5 . . ?
C25 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_ARC_DT_sb
_database_code_depnum_ccdc_archive 'CCDC 1418876'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 F6 N5 O2 P V'
_chemical_formula_sum            'C22 H20 F6 N5 O2 P V'
_chemical_formula_weight         582.34

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
O O 0.0106 0.0060 '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                   11.4384(10)
_cell_length_b                   13.6530(12)
_cell_length_c                   15.6328(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.740(3)
_cell_angle_gamma                90
_cell_volume                     2398.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             1180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.558
_shelx_estimated_absorpt_T_min   0.731
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart CCD Area Detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.3
_diffrn_reflns_number            54897
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.984
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5488
_reflns_number_gt                4089
_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 Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    ?
_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)+(0.1003P)²+3.5887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5488
_refine_ls_number_parameters     414
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1877
_refine_ls_wR_factor_gt          0.1630
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
C1 C 1.1430(3) 0.5424(3) 0.3984(2) 0.0364(7) Uani 1 1 d . . . . .
C2 C 1.2594(4) 0.5176(3) 0.4003(3) 0.0496(10) Uani 1 1 d . . . . .
C3 C 1.3106(4) 0.5435(4) 0.3324(3) 0.0630(13) Uani 1 1 d . . . . .
C4 C 1.2461(4) 0.5970(4) 0.2645(3) 0.0559(11) Uani 1 1 d . . . . .
C5 C 1.1295(3) 0.6206(2) 0.2660(2) 0.0332(7) Uani 1 1 d . . . . .
C6 C 1.0531(3) 0.6782(2) 0.1970(2) 0.0329(7) Uani 1 1 d . . . . .
C7 C 1.0981(4) 0.7292(3) 0.1331(2) 0.0482(9) Uani 1 1 d . . . . .
C8 C 1.0215(4) 0.7846(3) 0.0748(2) 0.0539(11) Uani 1 1 d . . . . .
C9 C 0.9040(4) 0.7879(3) 0.0794(2) 0.0478(10) Uani 1 1 d . . . . .
C10 C 0.8643(3) 0.7365(2) 0.1444(2) 0.0369(7) Uani 1 1 d . . . . .
C11 C 0.8348(3) 0.8098(2) 0.3849(2) 0.0362(7) Uani 1 1 d . . . . .
C12 C 0.8768(4) 0.8946(3) 0.4307(3) 0.0466(9) Uani 1 1 d . . . . .
C13 C 0.7992(5) 0.9656(3) 0.4488(3) 0.0617(12) Uani 1 1 d . . . . .
C14 C 0.6780(5) 0.9541(4) 0.4235(4) 0.0747(15) Uani 1 1 d . . . . .
C15 C 0.6358(5) 0.8726(4) 0.3792(4) 0.0712(14) Uani 1 1 d . . . . .
C16 C 0.7116(3) 0.7984(3) 0.3588(3) 0.0436(8) Uani 1 1 d . . . . .
C20 C 0.7644(3) 0.4624(3) 0.1778(3) 0.0456(9) Uani 1 1 d . . . . .
C21 C 0.7863(4) 0.3790(3) 0.1372(3) 0.0497(10) Uani 1 1 d . . . . .
C22 C 0.9458(3) 0.4223(3) 0.2272(2) 0.0391(8) Uani 1 1 d . . . . .
C19 C 0.6549(4) 0.5243(4) 0.1645(3) 0.0576(11) Uani 1 1 d . . . . .
C18 C 0.6243(4) 0.5592(3) 0.2480(4) 0.0575(12) Uani 1 1 d . . . . .
C17 C 0.6554(3) 0.7144(3) 0.3131(3) 0.0435(9) Uani 1 1 d . . . . .
N1 N 1.0769(2) 0.59246(18) 0.33239(16) 0.0291(6) Uani 1 1 d . . . . .
N2 N 0.9377(2) 0.68241(19) 0.20285(16) 0.0301(6) Uani 1 1 d . . . . .
N3 N 0.7059(2) 0.6373(2) 0.2903(2) 0.0382(6) Uani 1 1 d . . . . .
N4 N 0.8655(2) 0.48834(19) 0.23711(17) 0.0321(6) Uani 1 1 d . . . . .
N19 N 0.9006(3) 0.3554(2) 0.1691(2) 0.0409(7) Uani 1 1 d . . . . .
F1 F 1.4485(5) 0.8997(3) 0.0769(5) 0.178(3) Uani 1 1 d . . . . .
F2 F 1.4694(6) 0.8059(6) -0.0228(4) 0.188(3) Uani 1 1 d . . . . .
F3 F 1.3097(3) 0.7946(4) 0.0276(3) 0.1295(17) Uani 1 1 d . . . . .
F4 F 1.4460(7) 0.6780(4) 0.0511(7) 0.248(5) Uani 1 1 d . . . . .
F5 F 1.5790(3) 0.7795(4) 0.1090(4) 0.159(2) Uani 1 1 d . . . . .
F6 F 1.4142(5) 0.7635(8) 0.1560(4) 0.227(4) Uani 1 1 d . . . . .
P1 P 1.44603(11) 0.78911(9) 0.06892(9) 0.0619(3) Uani 1 1 d . . . . .
V1 V 0.88805(4) 0.60836(4) 0.32414(3) 0.02638(18) Uani 1 1 d . . . . .
O1 O 0.9119(2) 0.74263(16) 0.36796(15) 0.0346(5) Uani 1 1 d . . . . .
O2 O 0.8876(2) 0.54760(18) 0.41086(15) 0.0419(6) Uani 1 1 d . . . . .
H9 H 0.957(4) 0.898(3) 0.454(3) 0.053(13) Uiso 1 1 d . . . . .
H10 H 0.830(3) 1.023(3) 0.481(3) 0.044(10) Uiso 1 1 d . . . . .
H14 H 0.555(4) 0.580(3) 0.238(3) 0.056(13) Uiso 1 1 d . . . . .
H11 H 0.618(5) 1.008(4) 0.436(4) 0.092(17) Uiso 1 1 d . . . . .
H4 H 1.275(4) 0.617(3) 0.212(3) 0.065(14) Uiso 1 1 d . . . . .
H3 H 1.383(4) 0.527(4) 0.333(3) 0.060(13) Uiso 1 1 d . . . . .
H2 H 1.300(4) 0.476(3) 0.446(3) 0.062(13) Uiso 1 1 d . . . . .
H1 H 1.099(3) 0.521(3) 0.447(3) 0.043(10) Uiso 1 1 d . . . . .
H20 H 1.022(4) 0.425(3) 0.257(3) 0.056(13) Uiso 1 1 d . . . . .
H8 H 0.785(3) 0.736(2) 0.152(2) 0.028(9) Uiso 1 1 d . . . . .
H7 H 0.854(4) 0.823(3) 0.043(3) 0.044(11) Uiso 1 1 d . . . . .
H19 H 0.937(3) 0.314(3) 0.155(2) 0.033(10) Uiso 1 1 d . . . . .
H15 H 0.636(4) 0.483(3) 0.269(3) 0.054(12) Uiso 1 1 d . . . . .
H17 H 0.584(5) 0.488(4) 0.127(4) 0.085(17) Uiso 1 1 d . . . . .
H6 H 1.049(5) 0.823(4) 0.034(3) 0.077(15) Uiso 1 1 d . . . . .
H5 H 1.174(4) 0.724(3) 0.133(3) 0.061(14) Uiso 1 1 d . . . . .
H12 H 0.551(5) 0.860(4) 0.375(4) 0.086(17) Uiso 1 1 d . . . . .
H13 H 0.575(4) 0.715(4) 0.296(3) 0.066(14) Uiso 1 1 d . . . . .
H16 H 0.665(6) 0.587(5) 0.132(4) 0.10(2) Uiso 1 1 d . . . . .
H18 H 0.735(4) 0.345(3) 0.097(3) 0.057(12) 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
C1 N1 1.347(4) . ?
C1 C2 1.368(5) . ?
C1 H1 1.03(4) . ?
C2 C3 1.353(6) . ?
C2 H2 0.97(5) . ?
C3 C4 1.383(6) . ?
C3 H3 0.86(5) . ?
C4 C5 1.377(5) . ?
C4 H4 0.98(5) . ?
C5 N1 1.350(4) . ?
C5 C6 1.481(5) . ?
C6 N2 1.341(4) . ?
C6 C7 1.393(5) . ?
C7 C8 1.369(6) . ?
C7 H5 0.87(5) . ?
C8 C9 1.360(7) . ?
C8 H6 0.92(5) . ?
C9 C10 1.380(5) . ?
C9 H7 0.87(4) . ?
C10 N2 1.341(4) . ?
C10 H8 0.94(4) . ?
C11 O1 1.333(4) . ?
C11 C12 1.399(5) . ?
C11 C16 1.401(5) . ?
C12 C13 1.378(6) . ?
C12 H9 0.92(5) . ?
C13 C14 1.379(7) . ?
C13 H10 0.96(4) . ?
C14 C15 1.351(7) . ?
C14 H11 1.04(6) . ?
C15 C16 1.408(6) . ?
C15 H12 0.97(6) . ?
C16 C17 1.438(5) . ?
C20 C21 1.349(5) . ?
C20 N4 1.387(5) . ?
C20 C19 1.493(6) . ?
C21 N19 1.348(5) . ?
C21 H18 0.91(5) . ?
C22 N4 1.317(4) . ?
C22 N19 1.325(5) . ?
C22 H20 0.91(5) . ?
C19 C18 1.491(7) . ?
C19 H17 1.04(6) . ?
C19 H16 1.02(6) . ?
C18 N3 1.488(5) . ?
C18 H14 0.83(5) . ?
C18 H15 1.08(5) . ?
C17 N3 1.283(5) . ?
C17 H13 0.91(5) . ?
N1 V1 2.150(3) . ?
N2 V1 2.311(3) . ?
N3 V1 2.089(3) . ?
N4 V1 2.115(3) . ?
N19 H19 0.77(4) . ?
F1 P1 1.515(4) . ?
F2 P1 1.524(5) . ?
F3 P1 1.575(4) . ?
F4 P1 1.543(5) . ?
F5 P1 1.539(4) . ?
F6 P1 1.514(5) . ?
V1 O2 1.590(2) . ?
V1 O1 1.958(2) . ?

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
N1 C1 C2 123.2(3) . . ?
N1 C1 H1 115(2) . . ?
C2 C1 H1 122(2) . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 H2 122(3) . . ?
C1 C2 H2 119(3) . . ?
C2 C3 C4 119.6(4) . . ?
C2 C3 H3 119(3) . . ?
C4 C3 H3 121(3) . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 115(3) . . ?
C3 C4 H4 125(3) . . ?
N1 C5 C4 121.3(3) . . ?
N1 C5 C6 115.1(3) . . ?
C4 C5 C6 123.7(3) . . ?
N2 C6 C7 121.8(3) . . ?
N2 C6 C5 115.4(3) . . ?
C7 C6 C5 122.7(3) . . ?
C8 C7 C6 118.5(4) . . ?
C8 C7 H5 124(3) . . ?
C6 C7 H5 118(3) . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H6 119(3) . . ?
C7 C8 H6 121(3) . . ?
C8 C9 C10 119.1(4) . . ?
C8 C9 H7 121(3) . . ?
C10 C9 H7 119(3) . . ?
N2 C10 C9 122.1(4) . . ?
N2 C10 H8 115(2) . . ?
C9 C10 H8 123(2) . . ?
O1 C11 C12 119.6(3) . . ?
O1 C11 C16 122.2(3) . . ?
C12 C11 C16 118.2(3) . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H9 121(3) . . ?
C11 C12 H9 117(3) . . ?
C12 C13 C14 120.8(4) . . ?
C12 C13 H10 119(2) . . ?
C14 C13 H10 120(2) . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 H11 119(3) . . ?
C13 C14 H11 122(3) . . ?
C14 C15 C16 122.2(5) . . ?
C14 C15 H12 116(3) . . ?
C16 C15 H12 120(3) . . ?
C11 C16 C15 118.8(4) . . ?
C11 C16 C17 124.5(3) . . ?
C15 C16 C17 116.7(4) . . ?
C21 C20 N4 109.0(3) . . ?
C21 C20 C19 129.6(4) . . ?
N4 C20 C19 121.4(3) . . ?
N19 C21 C20 106.3(4) . . ?
N19 C21 H18 127(3) . . ?
C20 C21 H18 127(3) . . ?
N4 C22 N19 111.1(3) . . ?
N4 C22 H20 122(3) . . ?
N19 C22 H20 127(3) . . ?
C18 C19 C20 112.8(4) . . ?
C18 C19 H17 111(3) . . ?
C20 C19 H17 111(3) . . ?
C18 C19 H16 103(4) . . ?
C20 C19 H16 112(4) . . ?
H17 C19 H16 105(4) . . ?
N3 C18 C19 112.8(4) . . ?
N3 C18 H14 110(3) . . ?
C19 C18 H14 108(3) . . ?
N3 C18 H15 121(2) . . ?
C19 C18 H15 85(2) . . ?
H14 C18 H15 116(4) . . ?
N3 C17 C16 127.6(4) . . ?
N3 C17 H13 115(3) . . ?
C16 C17 H13 118(3) . . ?
C1 N1 C5 117.8(3) . . ?
C1 N1 V1 120.8(2) . . ?
C5 N1 V1 120.8(2) . . ?
C6 N2 C10 118.4(3) . . ?
C6 N2 V1 115.6(2) . . ?
C10 N2 V1 125.6(2) . . ?
C17 N3 C18 115.7(3) . . ?
C17 N3 V1 124.4(3) . . ?
C18 N3 V1 119.4(2) . . ?
C22 N4 C20 105.1(3) . . ?
C22 N4 V1 127.0(2) . . ?
C20 N4 V1 127.9(2) . . ?
C22 N19 C21 108.5(3) . . ?
C22 N19 H19 123(3) . . ?
C21 N19 H19 128(3) . . ?
F6 P1 F1 99.2(5) . . ?
F6 P1 F2 173.9(5) . . ?
F1 P1 F2 85.6(4) . . ?
F6 P1 F5 90.0(3) . . ?
F1 P1 F5 92.8(3) . . ?
F2 P1 F5 93.6(3) . . ?
F6 P1 F4 86.8(5) . . ?
F1 P1 F4 174.0(5) . . ?
F2 P1 F4 88.4(5) . . ?
F5 P1 F4 87.5(3) . . ?
F6 P1 F3 89.7(3) . . ?
F1 P1 F3 89.3(3) . . ?
F2 P1 F3 86.6(3) . . ?
F5 P1 F3 177.9(3) . . ?
F4 P1 F3 90.4(3) . . ?
O2 V1 O1 102.27(12) . . ?
O2 V1 N3 98.77(13) . . ?
O1 V1 N3 88.80(11) . . ?
O2 V1 N4 97.17(12) . . ?
O1 V1 N4 160.53(10) . . ?
N3 V1 N4 89.28(11) . . ?
O2 V1 N1 93.40(12) . . ?
O1 V1 N1 90.04(10) . . ?
N3 V1 N1 167.75(11) . . ?
N4 V1 N1 87.76(10) . . ?
O2 V1 N2 165.48(12) . . ?
O1 V1 N2 80.68(9) . . ?
N3 V1 N2 95.49(11) . . ?
N4 V1 N2 80.23(10) . . ?
N1 V1 N2 72.29(10) . . ?
C11 O1 V1 131.3(2) . . ?

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
N1 C1 C2 C3 -0.8(6) . . . . ?
C1 C2 C3 C4 2.2(7) . . . . ?
C2 C3 C4 C5 -1.8(8) . . . . ?
C3 C4 C5 N1 -0.1(7) . . . . ?
C3 C4 C5 C6 179.5(4) . . . . ?
N1 C5 C6 N2 -9.5(4) . . . . ?
C4 C5 C6 N2 170.9(4) . . . . ?
N1 C5 C6 C7 167.1(3) . . . . ?
C4 C5 C6 C7 -12.5(6) . . . . ?
N2 C6 C7 C8 -0.2(6) . . . . ?
C5 C6 C7 C8 -176.6(4) . . . . ?
C6 C7 C8 C9 -1.0(6) . . . . ?
C7 C8 C9 C10 1.4(6) . . . . ?
C8 C9 C10 N2 -0.8(6) . . . . ?
O1 C11 C12 C13 179.7(4) . . . . ?
C16 C11 C12 C13 -0.7(6) . . . . ?
C11 C12 C13 C14 1.0(7) . . . . ?
C12 C13 C14 C15 -0.9(9) . . . . ?
C13 C14 C15 C16 0.6(9) . . . . ?
O1 C11 C16 C15 179.9(4) . . . . ?
C12 C11 C16 C15 0.3(6) . . . . ?
O1 C11 C16 C17 1.0(6) . . . . ?
C12 C11 C16 C17 -178.5(4) . . . . ?
C14 C15 C16 C11 -0.3(8) . . . . ?
C14 C15 C16 C17 178.7(5) . . . . ?
N4 C20 C21 N19 -1.8(5) . . . . ?
C19 C20 C21 N19 176.3(4) . . . . ?
C21 C20 C19 C18 138.1(5) . . . . ?
N4 C20 C19 C18 -43.9(6) . . . . ?
C20 C19 C18 N3 73.1(5) . . . . ?
C11 C16 C17 N3 1.2(7) . . . . ?
C15 C16 C17 N3 -177.7(5) . . . . ?
C2 C1 N1 C5 -1.2(5) . . . . ?
C2 C1 N1 V1 170.1(3) . . . . ?
C4 C5 N1 C1 1.6(5) . . . . ?
C6 C5 N1 C1 -178.0(3) . . . . ?
C4 C5 N1 V1 -169.6(3) . . . . ?
C6 C5 N1 V1 10.8(4) . . . . ?
C7 C6 N2 C10 0.8(5) . . . . ?
C5 C6 N2 C10 177.5(3) . . . . ?
C7 C6 N2 V1 -172.4(3) . . . . ?
C5 C6 N2 V1 4.2(3) . . . . ?
C9 C10 N2 C6 -0.4(5) . . . . ?
C9 C10 N2 V1 172.2(3) . . . . ?
C16 C17 N3 C18 176.6(4) . . . . ?
C16 C17 N3 V1 5.6(6) . . . . ?
C19 C18 N3 C17 129.6(4) . . . . ?
C19 C18 N3 V1 -58.9(5) . . . . ?
N19 C22 N4 C20 -2.6(4) . . . . ?
N19 C22 N4 V1 177.9(2) . . . . ?
C21 C20 N4 C22 2.7(4) . . . . ?
C19 C20 N4 C22 -175.6(4) . . . . ?
C21 C20 N4 V1 -177.8(3) . . . . ?
C19 C20 N4 V1 3.8(6) . . . . ?
N4 C22 N19 C21 1.6(5) . . . . ?
C20 C21 N19 C22 0.2(5) . . . . ?
C12 C11 O1 V1 168.5(3) . . . . ?
C16 C11 O1 V1 -11.1(5) . . . . ?

_refine_diff_density_max         0.884
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.103

_shelxl_version_number           2014/6

