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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1907844'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-07-12 downloaded from the CCDC.
;

_audit_creation_date             2018-09-12T10:41:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C26 H17 Br N4 O3 V'
_chemical_formula_sum            'C26 H17 Br N4 O3 V'
_chemical_formula_weight         564.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4333(5)
_cell_length_b                   16.6359(10)
_cell_length_c                   16.7706(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.479(3)
_cell_angle_gamma                90
_cell_volume                     2288.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      28.07
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1132

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.528
_shelx_estimated_absorpt_T_max   0.897

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      -0.081051
_diffrn_orient_matrix_ub_12      -0.039436
_diffrn_orient_matrix_ub_13      0.011814
_diffrn_orient_matrix_ub_21      -0.026692
_diffrn_orient_matrix_ub_22      -0.017218
_diffrn_orient_matrix_ub_23      -0.058747
_diffrn_orient_matrix_ub_31      0.087101
_diffrn_orient_matrix_ub_32      -0.041973
_diffrn_orient_matrix_ub_33      0.012999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_number            11239
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.749
_diffrn_reflns_theta_max         28.442
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             5732
_reflns_number_gt                4745
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+1.0451P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5732
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.061
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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 0.9361(2) 0.28078(10) 0.82530(10) 0.0174(3) Uani 1 1 d . . . . .
C2 C 1.0670(2) 0.29576(11) 0.78599(11) 0.0205(4) Uani 1 1 d . . . . .
H2 H 1.0819 0.3486 0.7675 0.025 Uiso 1 1 calc R U . . .
C3 C 1.1704(2) 0.23663(11) 0.77445(11) 0.0204(4) Uani 1 1 d . . . . .
H3 H 1.2548 0.249 0.7476 0.025 Uiso 1 1 calc R U . . .
C4 C 1.1551(2) 0.15616(11) 0.80180(10) 0.0187(4) Uani 1 1 d . . . . .
C5 C 1.2614(2) 0.09437(12) 0.78842(11) 0.0232(4) Uani 1 1 d . . . . .
H5 H 1.3463 0.1068 0.7618 0.028 Uiso 1 1 calc R U . . .
C6 C 1.2441(2) 0.01699(12) 0.81322(12) 0.0271(4) Uani 1 1 d . . . . .
H6 H 1.3144 -0.0242 0.8026 0.033 Uiso 1 1 calc R U . . .
C7 C 1.1216(2) -0.00081(12) 0.85449(12) 0.0245(4) Uani 1 1 d . . . . .
H7 H 1.1103 -0.0542 0.8725 0.029 Uiso 1 1 calc R U . . .
C8 C 1.0174(2) 0.05816(11) 0.86928(11) 0.0209(4) Uani 1 1 d . . . . .
H8 H 0.9361 0.0451 0.898 0.025 Uiso 1 1 calc R U . . .
C9 C 1.03002(19) 0.13786(11) 0.84228(10) 0.0170(3) Uani 1 1 d . . . . .
C10 C 0.91805(19) 0.20102(10) 0.85376(10) 0.0164(3) Uani 1 1 d . . . . .
C11 C 0.58046(19) 0.19642(10) 0.94904(10) 0.0157(3) Uani 1 1 d . . . . .
C12 C 0.4527(2) 0.25121(10) 0.95004(10) 0.0154(3) Uani 1 1 d . . . . .
C13 C 0.33192(19) 0.22880(10) 0.99092(10) 0.0166(3) Uani 1 1 d . . . . .
H13 H 0.2432 0.2638 0.9917 0.02 Uiso 1 1 calc R U . . .
C14 C 0.3438(2) 0.15539(11) 1.02993(10) 0.0176(3) Uani 1 1 d . . . . .
C15 C 0.4712(2) 0.10149(11) 1.03057(12) 0.0231(4) Uani 1 1 d . . . . .
H15 H 0.4765 0.0516 1.0586 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5899(2) 0.12263(11) 0.98921(12) 0.0217(4) Uani 1 1 d . . . . .
H16 H 0.6773 0.0869 0.9883 0.026 Uiso 1 1 calc R U . . .
C17 C 0.8773(2) 0.36218(11) 1.02816(11) 0.0196(4) Uani 1 1 d . . . . .
H17 H 0.8997 0.3068 1.0222 0.024 Uiso 1 1 calc R U . . .
C18 C 0.9661(2) 0.40316(12) 1.09607(11) 0.0227(4) Uani 1 1 d . . . . .
H18 H 1.0489 0.3767 1.1354 0.027 Uiso 1 1 calc R U . . .
C19 C 0.9314(2) 0.48374(12) 1.10530(11) 0.0252(4) Uani 1 1 d . . . . .
H19 H 0.9898 0.5133 1.1513 0.03 Uiso 1 1 calc R U . . .
C20 C 0.8104(2) 0.52051(11) 1.04656(11) 0.0218(4) Uani 1 1 d . . . . .
H20 H 0.7837 0.5754 1.052 0.026 Uiso 1 1 calc R U . . .
C21 C 0.7285(2) 0.47579(10) 0.97945(11) 0.0165(3) Uani 1 1 d . . . . .
C22 C 0.60196(19) 0.50963(10) 0.91099(11) 0.0168(3) Uani 1 1 d . . . . .
C23 C 0.5400(2) 0.58713(11) 0.91188(12) 0.0234(4) Uani 1 1 d . . . . .
H23 H 0.5776 0.6209 0.9581 0.028 Uiso 1 1 calc R U . . .
C24 C 0.4239(2) 0.61485(12) 0.84554(14) 0.0288(5) Uani 1 1 d . . . . .
H24 H 0.3825 0.668 0.845 0.035 Uiso 1 1 calc R U . . .
C25 C 0.3688(2) 0.56376(12) 0.77983(13) 0.0285(4) Uani 1 1 d . . . . .
H25 H 0.2878 0.5811 0.7336 0.034 Uiso 1 1 calc R U . . .
C26 C 0.4333(2) 0.48699(12) 0.78236(11) 0.0224(4) Uani 1 1 d . . . . .
H26 H 0.3939 0.4519 0.7374 0.027 Uiso 1 1 calc R U . . .
N1 N 0.80433(16) 0.17697(9) 0.89528(9) 0.0165(3) Uani 1 1 d . . . . .
N2 N 0.68906(16) 0.22532(8) 0.90272(9) 0.0159(3) Uani 1 1 d . . . . .
N3 N 0.76132(16) 0.39753(9) 0.97076(9) 0.0153(3) Uani 1 1 d . . . . .
N4 N 0.54977(16) 0.46002(9) 0.84602(9) 0.0166(3) Uani 1 1 d . . . . .
O1 O 0.84474(14) 0.34102(7) 0.83480(8) 0.0196(3) Uani 1 1 d . . . . .
O2 O 0.45037(14) 0.32181(7) 0.91356(7) 0.0177(3) Uani 1 1 d . . . . .
O3 O 0.52848(15) 0.31626(8) 0.75835(8) 0.0238(3) Uani 1 1 d . . . . .
Br1 Br 0.17792(2) 0.12685(2) 1.08431(2) 0.02272(6) Uani 1 1 d . . . . .
V1 V 0.61993(3) 0.33638(2) 0.85138(2) 0.01509(7) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O1 1.297(2) . ?
C1 C10 1.430(2) . ?
C1 C2 1.433(2) . ?
C2 C3 1.357(3) . ?
C2 H2 0.95 . ?
C3 C4 1.431(3) . ?
C3 H3 0.95 . ?
C4 C9 1.414(2) . ?
C4 C5 1.416(3) . ?
C5 C6 1.371(3) . ?
C5 H5 0.95 . ?
C6 C7 1.403(3) . ?
C6 H6 0.95 . ?
C7 C8 1.378(3) . ?
C7 H7 0.95 . ?
C8 C9 1.413(3) . ?
C8 H8 0.95 . ?
C9 C10 1.455(2) . ?
C10 N1 1.370(2) . ?
C11 C16 1.394(2) . ?
C11 C12 1.414(2) . ?
C11 N2 1.416(2) . ?
C12 O2 1.322(2) . ?
C12 C13 1.404(2) . ?
C13 C14 1.378(2) . ?
C13 H13 0.95 . ?
C14 C15 1.397(3) . ?
C14 Br1 1.8999(16) . ?
C15 C16 1.389(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 N3 1.338(2) . ?
C17 C18 1.387(2) . ?
C17 H17 0.95 . ?
C18 C19 1.388(3) . ?
C18 H18 0.95 . ?
C19 C20 1.384(3) . ?
C19 H19 0.95 . ?
C20 C21 1.391(2) . ?
C20 H20 0.95 . ?
C21 N3 1.346(2) . ?
C21 C22 1.484(2) . ?
C22 N4 1.356(2) . ?
C22 C23 1.393(2) . ?
C23 C24 1.379(3) . ?
C23 H23 0.95 . ?
C24 C25 1.384(3) . ?
C24 H24 0.95 . ?
C25 C26 1.385(3) . ?
C25 H25 0.95 . ?
C26 N4 1.348(2) . ?
C26 H26 0.95 . ?
N1 N2 1.2901(19) . ?
N2 V1 2.0642(15) . ?
N3 V1 2.3134(14) . ?
N4 V1 2.1365(15) . ?
O1 V1 1.9808(12) . ?
O2 V1 1.9713(12) . ?
O3 V1 1.6063(13) . ?

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 C1 C10 124.29(15) . . ?
O1 C1 C2 117.76(16) . . ?
C10 C1 C2 117.92(16) . . ?
C3 C2 C1 121.89(17) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 121.59(16) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C9 C4 C5 119.38(17) . . ?
C9 C4 C3 119.22(16) . . ?
C5 C4 C3 121.40(16) . . ?
C6 C5 C4 121.15(17) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 119.39(17) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.84(18) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.77(17) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 118.43(16) . . ?
C8 C9 C10 122.38(15) . . ?
C4 C9 C10 119.19(16) . . ?
N1 C10 C1 125.62(15) . . ?
N1 C10 C9 114.15(15) . . ?
C1 C10 C9 120.18(15) . . ?
C16 C11 C12 121.31(15) . . ?
C16 C11 N2 126.36(15) . . ?
C12 C11 N2 112.31(15) . . ?
O2 C12 C13 121.83(15) . . ?
O2 C12 C11 119.74(15) . . ?
C13 C12 C11 118.42(15) . . ?
C14 C13 C12 119.10(16) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 122.89(16) . . ?
C13 C14 Br1 117.98(13) . . ?
C15 C14 Br1 119.13(13) . . ?
C16 C15 C14 118.41(17) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C15 C16 C11 119.84(16) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
N3 C17 C18 122.60(17) . . ?
N3 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
C17 C18 C19 118.58(17) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C20 C19 C18 119.13(17) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 118.94(17) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
N3 C21 C20 121.95(16) . . ?
N3 C21 C22 114.33(15) . . ?
C20 C21 C22 123.70(16) . . ?
N4 C22 C23 121.31(16) . . ?
N4 C22 C21 115.53(15) . . ?
C23 C22 C21 123.16(16) . . ?
C24 C23 C22 119.91(19) . . ?
C24 C23 H23 120 . . ?
C22 C23 H23 120 . . ?
C23 C24 C25 118.73(18) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C24 C25 C26 119.04(18) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
N4 C26 C25 122.67(18) . . ?
N4 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
N2 N1 C10 119.99(15) . . ?
N1 N2 C11 116.09(14) . . ?
N1 N2 V1 131.58(11) . . ?
C11 N2 V1 112.14(11) . . ?
C17 N3 C21 118.78(15) . . ?
C17 N3 V1 124.91(12) . . ?
C21 N3 V1 116.21(11) . . ?
C26 N4 C22 118.30(16) . . ?
C26 N4 V1 119.82(12) . . ?
C22 N4 V1 121.15(11) . . ?
C1 O1 V1 127.08(11) . . ?
C12 O2 V1 114.80(10) . . ?
O3 V1 O2 104.18(6) . . ?
O3 V1 O1 97.48(6) . . ?
O2 V1 O1 156.22(5) . . ?
O3 V1 N2 104.10(6) . . ?
O2 V1 N2 80.71(5) . . ?
O1 V1 N2 84.66(5) . . ?
O3 V1 N4 95.40(6) . . ?
O2 V1 N4 84.99(5) . . ?
O1 V1 N4 102.78(5) . . ?
N2 V1 N4 158.10(6) . . ?
O3 V1 N3 165.05(6) . . ?
O2 V1 N3 83.53(5) . . ?
O1 V1 N3 77.72(5) . . ?
N2 V1 N3 89.66(5) . . ?
N4 V1 N3 72.24(5) . . ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1907845'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-07-12 downloaded from the CCDC.
;

_audit_creation_date             2018-09-19T15:26:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C26 H18 N4 O3 V, H2 O'
_chemical_formula_sum            'C26 H20 N4 O4 V'
_chemical_formula_weight         503.4

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6015(7)
_cell_length_b                   10.3718(9)
_cell_length_c                   12.5377(11)
_cell_angle_alpha                93.200(6)
_cell_angle_beta                 90.428(5)
_cell_angle_gamma                104.447(5)
_cell_volume                     1081.20(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5040
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.16
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             518

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.99

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      -0.106517
_diffrn_orient_matrix_ub_12      -0.065149
_diffrn_orient_matrix_ub_13      -0.013276
_diffrn_orient_matrix_ub_21      0.050097
_diffrn_orient_matrix_ub_22      -0.053311
_diffrn_orient_matrix_ub_23      -0.052044
_diffrn_orient_matrix_ub_31      0.023758
_diffrn_orient_matrix_ub_32      -0.053494
_diffrn_orient_matrix_ub_33      0.059159
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_number            9623
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.627
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.944
_reflns_Friedel_coverage         0
_reflns_number_total             5105
_reflns_number_gt                3628
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+0.5134P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5105
_refine_ls_number_parameters     337
_refine_ls_number_restraints     6
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.074

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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 0.4924(3) 0.1497(2) 0.13106(18) 0.0165(5) Uani 1 1 d . . . . .
C2 C 0.6202(3) 0.0936(2) 0.09671(19) 0.0188(5) Uani 1 1 d . . . . .
H2 H 0.6529 0.0321 0.1398 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6962(3) 0.1261(2) 0.00375(19) 0.0202(5) Uani 1 1 d . . . . .
H3 H 0.7822 0.0878 -0.0158 0.024 Uiso 1 1 calc R U . . .
C4 C 0.6514(3) 0.2155(2) -0.06528(19) 0.0187(5) Uani 1 1 d . . . . .
C5 C 0.7321(3) 0.2499(2) -0.16178(19) 0.0212(5) Uani 1 1 d . . . . .
H5 H 0.818 0.2117 -0.1814 0.025 Uiso 1 1 calc R U . . .
C6 C 0.6891(3) 0.3365(2) -0.22701(19) 0.0228(6) Uani 1 1 d . . . . .
H6 H 0.7446 0.3581 -0.2914 0.027 Uiso 1 1 calc R U . . .
C7 C 0.5620(3) 0.3937(2) -0.19851(19) 0.0222(5) Uani 1 1 d . . . . .
H7 H 0.5308 0.4533 -0.2442 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4828(3) 0.3636(2) -0.10441(19) 0.0182(5) Uani 1 1 d . . . . .
H8 H 0.3988 0.4046 -0.0853 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5238(3) 0.2734(2) -0.03604(18) 0.0167(5) Uani 1 1 d . . . . .
C10 C 0.4424(3) 0.2393(2) 0.06444(18) 0.0157(5) Uani 1 1 d . . . . .
C12 C 0.0603(3) 0.3391(2) 0.29260(19) 0.0186(5) Uani 1 1 d . . . . .
C13 C -0.0706(3) 0.3927(2) 0.3151(2) 0.0236(6) Uani 1 1 d . . . . .
H13 H -0.1029 0.4023 0.3868 0.028 Uiso 1 1 calc R U . . .
C14 C -0.1526(3) 0.4315(2) 0.2329(2) 0.0251(6) Uani 1 1 d . . . . .
H14 H -0.2428 0.4661 0.2488 0.03 Uiso 1 1 calc R U . . .
C15 C -0.1065(3) 0.4214(2) 0.1270(2) 0.0236(6) Uani 1 1 d . . . . .
H15 H -0.1655 0.4479 0.0715 0.028 Uiso 1 1 calc R U . . .
C16 C 0.0252(3) 0.3725(2) 0.1033(2) 0.0212(5) Uani 1 1 d . . . . .
H16 H 0.0584 0.3661 0.0315 0.025 Uiso 1 1 calc R U . . .
C11 C 0.1086(3) 0.3328(2) 0.18511(19) 0.0178(5) Uani 1 1 d . . . . .
C17 C 0.0096(3) -0.0026(2) 0.19417(19) 0.0189(5) Uani 1 1 d . . . . .
H17 H 0.0256 0.0578 0.1387 0.023 Uiso 1 1 calc R U . . .
C18 C -0.1113(3) -0.1185(2) 0.18092(19) 0.0202(5) Uani 1 1 d . . . . .
H18 H -0.1761 -0.1377 0.1175 0.024 Uiso 1 1 calc R U . . .
C19 C -0.1359(3) -0.2059(2) 0.2618(2) 0.0222(5) Uani 1 1 d . . . . .
H19 H -0.2197 -0.2855 0.2555 0.027 Uiso 1 1 calc R U . . .
C20 C -0.0373(3) -0.1765(2) 0.3523(2) 0.0205(5) Uani 1 1 d . . . . .
H20 H -0.0516 -0.2358 0.4086 0.025 Uiso 1 1 calc R U . . .
C21 C 0.0830(3) -0.0584(2) 0.35929(19) 0.0174(5) Uani 1 1 d . . . . .
C22 C 0.1962(3) -0.0193(2) 0.45241(18) 0.0166(5) Uani 1 1 d . . . . .
C23 C 0.1929(3) -0.1006(2) 0.53672(19) 0.0212(5) Uani 1 1 d . . . . .
H23 H 0.1147 -0.1834 0.5372 0.025 Uiso 1 1 calc R U . . .
C24 C 0.3039(3) -0.0611(2) 0.6204(2) 0.0216(5) Uani 1 1 d . . . . .
H24 H 0.3052 -0.1171 0.6776 0.026 Uiso 1 1 calc R U . . .
C25 C 0.4127(3) 0.0619(2) 0.61842(19) 0.0211(5) Uani 1 1 d . . . . .
H25 H 0.4888 0.0925 0.6753 0.025 Uiso 1 1 calc R U . . .
C26 C 0.4097(3) 0.1395(2) 0.53343(19) 0.0182(5) Uani 1 1 d . . . . .
H26 H 0.484 0.2244 0.5336 0.022 Uiso 1 1 calc R U . . .
N1 N 0.3119(2) 0.29059(18) 0.08089(15) 0.0165(4) Uani 1 1 d . . . . .
N2 N 0.2474(2) 0.28381(18) 0.17403(15) 0.0169(4) Uani 1 1 d . . . . .
N3 N 0.1058(2) 0.02920(19) 0.28166(15) 0.0165(4) Uani 1 1 d . . . . .
N4 N 0.3053(2) 0.10022(19) 0.44925(15) 0.0171(4) Uani 1 1 d . . . . .
O1 O 0.42226(18) 0.11121(15) 0.22013(12) 0.0184(4) Uani 1 1 d . . . . .
O2 O 0.13972(19) 0.29367(16) 0.36863(13) 0.0209(4) Uani 1 1 d . . . . .
O3 O 0.47020(19) 0.33290(16) 0.35713(13) 0.0242(4) Uani 1 1 d . . . . .
V1 V 0.31574(5) 0.21901(4) 0.31481(3) 0.01759(12) Uani 1 1 d . . . . .
O4 O -0.2927(5) 0.4446(4) 0.5217(3) 0.0395(10) Uani 0.5 1 d D . P A 1
H4P H -0.375(4) 0.440(5) 0.489(5) 0.059 Uiso 0.5 1 d D U P B 1
H4O H -0.264(7) 0.520(2) 0.545(5) 0.059 Uiso 0.5 1 d D U P C 1
O5 O -0.3025(5) 0.5718(4) 0.4355(3) 0.0441(11) Uani 0.5 1 d D . P D 2
H5P H -0.361(7) 0.498(3) 0.435(4) 0.066 Uiso 0.5 1 d D U P E 2
H5O H -0.268(8) 0.588(6) 0.4955(19) 0.066 Uiso 0.5 1 d D U P F 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O1 1.308(3) . ?
C1 C10 1.423(3) . ?
C1 C2 1.425(3) . ?
C2 C3 1.358(3) . ?
C2 H2 0.95 . ?
C3 C4 1.422(3) . ?
C3 H3 0.95 . ?
C4 C9 1.417(3) . ?
C4 C5 1.418(3) . ?
C5 C6 1.362(3) . ?
C5 H5 0.95 . ?
C6 C7 1.407(3) . ?
C6 H6 0.95 . ?
C7 C8 1.379(3) . ?
C7 H7 0.95 . ?
C8 C9 1.409(3) . ?
C8 H8 0.95 . ?
C9 C10 1.463(3) . ?
C10 N1 1.370(3) . ?
C12 O2 1.341(3) . ?
C12 C13 1.399(3) . ?
C12 C11 1.416(3) . ?
C13 C14 1.378(4) . ?
C13 H13 0.95 . ?
C14 C15 1.395(4) . ?
C14 H14 0.95 . ?
C15 C16 1.380(3) . ?
C15 H15 0.95 . ?
C16 C11 1.386(3) . ?
C16 H16 0.95 . ?
C11 N2 1.414(3) . ?
C17 N3 1.344(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.95 . ?
C18 C19 1.380(3) . ?
C18 H18 0.95 . ?
C19 C20 1.384(3) . ?
C19 H19 0.95 . ?
C20 C21 1.390(3) . ?
C20 H20 0.95 . ?
C21 N3 1.351(3) . ?
C21 C22 1.486(3) . ?
C22 N4 1.358(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.386(3) . ?
C23 H23 0.95 . ?
C24 C25 1.383(3) . ?
C24 H24 0.95 . ?
C25 C26 1.375(3) . ?
C25 H25 0.95 . ?
C26 N4 1.357(3) . ?
C26 H26 0.95 . ?
N1 N2 1.295(3) . ?
N2 V1 2.056(2) . ?
N3 V1 2.3307(19) . ?
N4 V1 2.132(2) . ?
O1 V1 1.9693(15) . ?
O2 V1 1.9721(16) . ?
O3 V1 1.6057(16) . ?
O4 H4P 0.801(5) . ?
O4 H4O 0.800(5) . ?
O5 H5P 0.801(5) . ?
O5 H5O 0.800(5) . ?

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 C1 C10 123.4(2) . . ?
O1 C1 C2 118.0(2) . . ?
C10 C1 C2 118.6(2) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 122.1(2) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C9 C4 C5 119.0(2) . . ?
C9 C4 C3 119.1(2) . . ?
C5 C4 C3 121.9(2) . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 121.3(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C4 118.3(2) . . ?
C8 C9 C10 122.7(2) . . ?
C4 C9 C10 118.9(2) . . ?
N1 C10 C1 125.4(2) . . ?
N1 C10 C9 114.5(2) . . ?
C1 C10 C9 119.9(2) . . ?
O2 C12 C13 122.4(2) . . ?
O2 C12 C11 119.6(2) . . ?
C13 C12 C11 118.0(2) . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 121.6(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 119.4(2) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
C16 C11 N2 126.1(2) . . ?
C16 C11 C12 121.5(2) . . ?
N2 C11 C12 112.4(2) . . ?
N3 C17 C18 123.3(2) . . ?
N3 C17 H17 118.3 . . ?
C18 C17 H17 118.3 . . ?
C19 C18 C17 118.5(2) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C18 C19 C20 119.4(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C21 118.7(2) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
N3 C21 C20 122.4(2) . . ?
N3 C21 C22 115.0(2) . . ?
C20 C21 C22 122.6(2) . . ?
N4 C22 C23 121.8(2) . . ?
N4 C22 C21 116.1(2) . . ?
C23 C22 C21 122.1(2) . . ?
C22 C23 C24 119.9(2) . . ?
C22 C23 H23 120 . . ?
C24 C23 H23 120 . . ?
C25 C24 C23 118.3(2) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C26 C25 C24 119.4(2) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
N4 C26 C25 122.9(2) . . ?
N4 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?
N2 N1 C10 118.9(2) . . ?
N1 N2 C11 116.5(2) . . ?
N1 N2 V1 131.17(15) . . ?
C11 N2 V1 112.29(15) . . ?
C17 N3 C21 117.6(2) . . ?
C17 N3 V1 127.30(16) . . ?
C21 N3 V1 115.04(15) . . ?
C26 N4 C22 117.6(2) . . ?
C26 N4 V1 121.33(16) . . ?
C22 N4 V1 121.04(15) . . ?
C1 O1 V1 125.05(14) . . ?
C12 O2 V1 114.13(14) . . ?
O3 V1 O1 99.34(8) . . ?
O3 V1 O2 101.25(8) . . ?
O1 V1 O2 157.12(7) . . ?
O3 V1 N2 105.05(8) . . ?
O1 V1 N2 83.93(7) . . ?
O2 V1 N2 81.19(7) . . ?
O3 V1 N4 95.64(8) . . ?
O1 V1 N4 95.98(7) . . ?
O2 V1 N4 91.85(7) . . ?
N2 V1 N4 159.07(7) . . ?
O3 V1 N3 168.18(8) . . ?
O1 V1 N3 79.74(6) . . ?
O2 V1 N3 82.11(6) . . ?
N2 V1 N3 86.62(7) . . ?
N4 V1 N3 72.83(7) . . ?
H4P O4 H4O 105.1(9) . . ?
H5P O5 H5O 105.0(9) . . ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1907846'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-07-12 downloaded from the CCDC.
;

_audit_creation_date             2018-09-19T15:42:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C28 H18 N4 O3 V'
_chemical_formula_sum            'C28 H18 N4 O3 V'
_chemical_formula_weight         509.4

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.148(2)
_cell_length_b                   9.459(3)
_cell_length_c                   14.752(4)
_cell_angle_alpha                93.473(18)
_cell_angle_beta                 93.065(18)
_cell_angle_gamma                109.172(15)
_cell_volume                     1068.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1014
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      20.81
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       shard
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             522

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_T_max  0.745
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.99

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.034979
_diffrn_orient_matrix_ub_12      0.008917
_diffrn_orient_matrix_ub_13      -0.063915
_diffrn_orient_matrix_ub_21      -0.057926
_diffrn_orient_matrix_ub_22      0.077214
_diffrn_orient_matrix_ub_23      -0.00776
_diffrn_orient_matrix_ub_31      0.111393
_diffrn_orient_matrix_ub_32      0.081079
_diffrn_orient_matrix_ub_33      0.022236
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.1396
_diffrn_reflns_number            6036
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.387
_diffrn_reflns_theta_max         25.401
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_Friedel_coverage         0
_reflns_number_total             3909
_reflns_number_gt                2318
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3909
_refine_ls_number_parameters     325
_refine_ls_number_restraints     36
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.122
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.61
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.093

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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 0.4447(5) 0.8233(5) 0.8215(3) 0.0184(11) Uani 1 1 d . . . . .
C2 C 0.3249(5) 0.8995(5) 0.8438(3) 0.0201(11) Uani 1 1 d . . . . .
H2 H 0.2821 0.9469 0.7975 0.024 Uiso 1 1 calc R U . . .
C3 C 0.2712(6) 0.9063(5) 0.9277(3) 0.0257(12) Uani 1 1 d . . . . .
H3 H 0.192 0.9588 0.9392 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3291(6) 0.8371(5) 1.0004(3) 0.0232(12) Uani 1 1 d . . . . .
C5 C 0.2655(6) 0.8399(5) 1.0872(3) 0.0269(12) Uani 1 1 d . . . . .
H5 H 0.1823 0.8885 1.0978 0.032 Uiso 1 1 calc R U . . .
C6 C 0.3227(6) 0.7730(5) 1.1565(3) 0.0281(12) Uani 1 1 d . . . . .
H6 H 0.2776 0.774 1.2145 0.034 Uiso 1 1 calc R U . . .
C7 C 0.4478(6) 0.7032(5) 1.1419(3) 0.0286(12) Uani 1 1 d . . . . .
H7 H 0.4893 0.6594 1.1905 0.034 Uiso 1 1 calc R U . . .
C8 C 0.5111(6) 0.6977(5) 1.0570(3) 0.0239(12) Uani 1 1 d . . . . .
H8 H 0.5942 0.6487 1.0475 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4530(6) 0.7646(5) 0.9840(3) 0.0225(12) Uani 1 1 d . . . . .
C10 C 0.5133(5) 0.7592(5) 0.8927(3) 0.0185(11) Uani 1 1 d . . . . .
C11 C 0.8384(5) 0.6203(5) 0.8072(3) 0.0205(11) Uani 1 1 d . . . . .
C16 C 0.9268(6) 0.5930(5) 0.8842(3) 0.0267(12) Uani 1 1 d . . . . .
H16 H 0.8939 0.6118 0.9434 0.032 Uiso 1 1 calc R U . . .
C15 C 1.0631(6) 0.5381(5) 0.8734(3) 0.0280(13) Uani 1 1 d . . . . .
H15 H 1.1226 0.5164 0.9251 0.034 Uiso 1 1 calc R U . . .
C14 C 1.1129(6) 0.5146(5) 0.7858(3) 0.0241(12) Uani 1 1 d . . . . .
H14 H 1.208 0.4787 0.7787 0.029 Uiso 1 1 calc R U . . .
C13 C 1.0261(6) 0.5427(5) 0.7094(3) 0.0250(12) Uani 1 1 d . . . . .
H13 H 1.0621 0.5265 0.6506 0.03 Uiso 1 1 calc R U . . .
C12 C 0.8858(5) 0.5950(5) 0.7184(3) 0.0199(11) Uani 1 1 d . . . . .
C17 C 0.9496(5) 0.9922(5) 0.7431(3) 0.0204(11) Uani 1 1 d . . . . .
H17 H 0.9521 0.9477 0.7989 0.024 Uiso 1 1 calc R U . . .
C18 C 1.0785(5) 1.1293(5) 0.7317(3) 0.0217(11) Uani 1 1 d . . . . .
H18 H 1.1673 1.1754 0.779 0.026 Uiso 1 1 calc R U . . .
C19 C 1.0765(5) 1.1965(5) 0.6529(3) 0.0215(11) Uani 1 1 d . . . . .
H19 H 1.1637 1.2894 0.6449 0.026 Uiso 1 1 calc R U . . .
C20 C 0.9439(5) 1.1270(5) 0.5831(3) 0.0178(11) Uani 1 1 d . U . . .
C21 C 0.8224(5) 0.9891(5) 0.5997(3) 0.0153(10) Uani 1 1 d . U . . .
C22 C 0.9300(5) 1.1891(5) 0.4982(3) 0.0205(11) Uani 1 1 d . U . . .
H22 H 1.0126 1.2825 0.4867 0.025 Uiso 1 1 calc R U . . .
C23 C 0.7993(5) 1.1152(5) 0.4340(3) 0.0200(11) Uani 1 1 d . U . . .
H23 H 0.7908 1.1596 0.3786 0.024 Uiso 1 1 calc R U . . .
C24 C 0.6735(5) 0.9721(5) 0.4471(3) 0.0191(11) Uani 1 1 d . U . . .
C25 C 0.6878(5) 0.9085(5) 0.5295(3) 0.0155(10) Uani 1 1 d . U . . .
C26 C 0.5403(5) 0.8902(5) 0.3820(3) 0.0197(11) Uani 1 1 d . . . . .
H26 H 0.5243 0.9305 0.3261 0.024 Uiso 1 1 calc R U . . .
C27 C 0.4327(5) 0.7510(5) 0.3997(3) 0.0207(11) Uani 1 1 d . . . . .
H27 H 0.343 0.6934 0.3553 0.025 Uiso 1 1 calc R U . . .
C28 C 0.4549(5) 0.6943(5) 0.4821(3) 0.0184(11) Uani 1 1 d . . . . .
H28 H 0.38 0.5969 0.4926 0.022 Uiso 1 1 calc R U . . .
N2 N 0.6954(4) 0.6745(4) 0.8078(3) 0.0194(9) Uani 1 1 d . . . . .
N3 N 0.8240(4) 0.9224(4) 0.6786(2) 0.0182(9) Uani 1 1 d . . . . .
N4 N 0.5767(4) 0.7706(4) 0.5474(2) 0.0178(9) Uani 1 1 d . . . . .
O1 O 0.4901(4) 0.8222(3) 0.7379(2) 0.0196(7) Uani 1 1 d . . . . .
O2 O 0.7951(4) 0.6203(3) 0.6467(2) 0.0237(8) Uani 1 1 d . . . . .
O3 O 0.4352(4) 0.5378(3) 0.6562(2) 0.0226(8) Uani 1 1 d . . . . .
V1 V 0.59993(10) 0.68888(8) 0.67761(5) 0.0199(3) Uani 1 1 d . . . . .
N1 N 0.6443(5) 0.6983(4) 0.8866(3) 0.0217(9) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O1 1.308(5) . ?
C1 C10 1.421(6) . ?
C1 C2 1.431(6) . ?
C2 C3 1.341(6) . ?
C2 H2 0.95 . ?
C3 C4 1.426(7) . ?
C3 H3 0.95 . ?
C4 C5 1.408(6) . ?
C4 C9 1.418(7) . ?
C5 C6 1.373(7) . ?
C5 H5 0.95 . ?
C6 C7 1.404(7) . ?
C6 H6 0.95 . ?
C7 C8 1.384(6) . ?
C7 H7 0.95 . ?
C8 C9 1.417(6) . ?
C8 H8 0.95 . ?
C9 C10 1.461(6) . ?
C10 N1 1.373(6) . ?
C11 C16 1.395(6) . ?
C11 C12 1.414(6) . ?
C11 N2 1.419(6) . ?
C16 C15 1.384(6) . ?
C16 H16 0.95 . ?
C15 C14 1.402(7) . ?
C15 H15 0.95 . ?
C14 C13 1.384(6) . ?
C14 H14 0.95 . ?
C13 C12 1.396(6) . ?
C13 H13 0.95 . ?
C12 O2 1.336(5) . ?
C17 N3 1.328(5) . ?
C17 C18 1.401(6) . ?
C17 H17 0.95 . ?
C18 C19 1.360(6) . ?
C18 H18 0.95 . ?
C19 C20 1.411(6) . ?
C19 H19 0.95 . ?
C20 C21 1.400(6) . ?
C20 C22 1.429(6) . ?
C21 N3 1.359(5) . ?
C21 C25 1.445(5) . ?
C22 C23 1.358(6) . ?
C22 H22 0.95 . ?
C23 C24 1.436(6) . ?
C23 H23 0.95 . ?
C24 C26 1.395(6) . ?
C24 C25 1.404(6) . ?
C25 N4 1.372(5) . ?
C26 C27 1.370(6) . ?
C26 H26 0.95 . ?
C27 C28 1.386(6) . ?
C27 H27 0.95 . ?
C28 N4 1.332(5) . ?
C28 H28 0.95 . ?
N2 N1 1.286(5) . ?
N2 V1 2.063(4) . ?
N3 V1 2.357(3) . ?
N4 V1 2.136(4) . ?
O1 V1 1.967(3) . ?
O2 V1 1.969(3) . ?
O3 V1 1.607(3) . ?

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 C1 C10 123.9(4) . . ?
O1 C1 C2 118.1(4) . . ?
C10 C1 C2 118.0(4) . . ?
C3 C2 C1 122.2(5) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 122.0(5) . . ?
C2 C3 H3 119 . . ?
C4 C3 H3 119 . . ?
C5 C4 C9 120.0(5) . . ?
C5 C4 C3 121.2(5) . . ?
C9 C4 C3 118.7(4) . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.2(5) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.3(5) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.7(5) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 118.2(4) . . ?
C8 C9 C10 122.7(5) . . ?
C4 C9 C10 119.1(4) . . ?
N1 C10 C1 125.9(4) . . ?
N1 C10 C9 114.1(4) . . ?
C1 C10 C9 119.9(4) . . ?
C16 C11 C12 121.7(5) . . ?
C16 C11 N2 125.4(4) . . ?
C12 C11 N2 112.9(4) . . ?
C15 C16 C11 119.2(5) . . ?
C15 C16 H16 120.4 . . ?
C11 C16 H16 120.4 . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C13 C14 C15 121.2(5) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C13 C12 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
O2 C12 C13 122.5(4) . . ?
O2 C12 C11 119.4(4) . . ?
C13 C12 C11 118.1(4) . . ?
N3 C17 C18 122.4(4) . . ?
N3 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120 . . ?
C17 C18 H18 120 . . ?
C18 C19 C20 119.5(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 116.7(4) . . ?
C21 C20 C22 119.7(4) . . ?
C19 C20 C22 123.7(4) . . ?
N3 C21 C20 123.8(4) . . ?
N3 C21 C25 116.6(4) . . ?
C20 C21 C25 119.6(4) . . ?
C23 C22 C20 120.4(4) . . ?
C23 C22 H22 119.8 . . ?
C20 C22 H22 119.8 . . ?
C22 C23 C24 122.0(4) . . ?
C22 C23 H23 119 . . ?
C24 C23 H23 119 . . ?
C26 C24 C25 117.8(4) . . ?
C26 C24 C23 124.0(4) . . ?
C25 C24 C23 118.2(4) . . ?
N4 C25 C24 122.4(4) . . ?
N4 C25 C21 117.4(4) . . ?
C24 C25 C21 120.1(4) . . ?
C27 C26 C24 119.3(4) . . ?
C27 C26 H26 120.4 . . ?
C24 C26 H26 120.4 . . ?
C26 C27 C28 119.9(4) . . ?
C26 C27 H27 120 . . ?
C28 C27 H27 120 . . ?
N4 C28 C27 122.8(4) . . ?
N4 C28 H28 118.6 . . ?
C27 C28 H28 118.6 . . ?
N1 N2 C11 116.1(4) . . ?
N1 N2 V1 132.1(3) . . ?
C11 N2 V1 111.7(3) . . ?
C17 N3 C21 117.7(4) . . ?
C17 N3 V1 129.3(3) . . ?
C21 N3 V1 113.0(2) . . ?
C28 N4 C25 117.7(4) . . ?
C28 N4 V1 122.6(3) . . ?
C25 N4 V1 119.6(3) . . ?
C1 O1 V1 127.9(3) . . ?
C12 O2 V1 114.5(3) . . ?
O3 V1 O1 100.85(14) . . ?
O3 V1 O2 102.06(14) . . ?
O1 V1 O2 155.42(12) . . ?
O3 V1 N2 104.63(14) . . ?
O1 V1 N2 84.43(14) . . ?
O2 V1 N2 81.32(15) . . ?
O3 V1 N4 94.75(14) . . ?
O1 V1 N4 93.22(13) . . ?
O2 V1 N4 93.61(14) . . ?
N2 V1 N4 160.58(13) . . ?
O3 V1 N3 167.96(14) . . ?
O1 V1 N3 79.43(12) . . ?
O2 V1 N3 80.01(12) . . ?
N2 V1 N3 87.39(13) . . ?
N4 V1 N3 73.25(13) . . ?
N2 N1 C10 119.2(4) . . ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1907847'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-07-12 downloaded from the CCDC.
;

_audit_creation_date             2019-03-11T11:28:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C27 H20 N4 O3 V'
_chemical_formula_sum            'C27 H20 N4 O3 V'
_chemical_formula_weight         499.41

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8888(9)
_cell_length_b                   18.6789(15)
_cell_length_c                   24.445(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.725(5)
_cell_angle_gamma                90
_cell_volume                     4463.1(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9764
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.89
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2056

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_T_max  0.744
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.94

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.059367
_diffrn_orient_matrix_ub_12      0.010758
_diffrn_orient_matrix_ub_13      0.035929
_diffrn_orient_matrix_ub_21      -0.079346
_diffrn_orient_matrix_ub_22      -0.008536
_diffrn_orient_matrix_ub_23      0.020118
_diffrn_orient_matrix_ub_31      0.025432
_diffrn_orient_matrix_ub_32      -0.051745
_diffrn_orient_matrix_ub_33      0.004151
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_number            21870
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.378
_diffrn_reflns_theta_max         28.432
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_Friedel_coverage         0
_reflns_number_total             11119
_reflns_number_gt                7946
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+3.5269P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         11119
_refine_ls_number_parameters     633
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.071

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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 0.2813(2) 0.64557(11) 0.30640(9) 0.0195(4) Uani 1 1 d . . . . .
C2 C 0.1773(2) 0.63800(11) 0.34091(9) 0.0230(5) Uani 1 1 d . . . . .
H2 H 0.195 0.6539 0.3782 0.028 Uiso 1 1 calc R U . . .
C3 C 0.0536(2) 0.60836(11) 0.32126(9) 0.0226(5) Uani 1 1 d . . . . .
H3 H -0.0133 0.6046 0.3452 0.027 Uiso 1 1 calc R U . . .
C4 C 0.0215(2) 0.58287(11) 0.26581(9) 0.0200(4) Uani 1 1 d . . . . .
C5 C -0.1101(2) 0.55587(11) 0.24453(10) 0.0243(5) Uani 1 1 d . . . . .
H5 H -0.1789 0.5543 0.2677 0.029 Uiso 1 1 calc R U . . .
C6 C -0.1395(2) 0.53200(12) 0.19110(10) 0.0263(5) Uani 1 1 d . . . . .
H6 H -0.2284 0.5146 0.1772 0.032 Uiso 1 1 calc R U . . .
C7 C -0.0377(2) 0.53335(12) 0.15701(9) 0.0251(5) Uani 1 1 d . . . . .
H7 H -0.0577 0.516 0.1201 0.03 Uiso 1 1 calc R U . . .
C8 C 0.0912(2) 0.55952(11) 0.17633(9) 0.0210(4) Uani 1 1 d . . . . .
H8 H 0.159 0.5599 0.1526 0.025 Uiso 1 1 calc R U . . .
C9 C 0.1234(2) 0.58575(10) 0.23101(9) 0.0186(4) Uani 1 1 d . . . . .
C10 C 0.2549(2) 0.61812(10) 0.25153(8) 0.0177(4) Uani 1 1 d . . . . .
C11 C 0.5305(2) 0.66279(11) 0.17928(9) 0.0184(4) Uani 1 1 d . . . . .
C12 C 0.6577(2) 0.69611(10) 0.19548(8) 0.0180(4) Uani 1 1 d . . . . .
C13 C 0.7419(2) 0.70800(11) 0.15523(9) 0.0197(4) Uani 1 1 d . . . . .
H13 H 0.8282 0.7305 0.1655 0.024 Uiso 1 1 calc R U . . .
C14 C 0.7019(2) 0.68767(10) 0.10058(8) 0.0176(4) Uani 1 1 d . . . . .
C15 C 0.5734(2) 0.65575(11) 0.08525(9) 0.0205(4) Uani 1 1 d . . . . .
H15 H 0.5445 0.6427 0.0477 0.025 Uiso 1 1 calc R U . . .
C16 C 0.4883(2) 0.64309(11) 0.12425(9) 0.0210(4) Uani 1 1 d . . . . .
H16 H 0.4017 0.6211 0.1136 0.025 Uiso 1 1 calc R U . . .
C17 C 0.7983(2) 0.69931(12) 0.05912(9) 0.0223(4) Uani 1 1 d . . . . .
H17A H 0.844 0.7457 0.066 0.033 Uiso 1 1 calc R U . . .
H17B H 0.7466 0.6987 0.0216 0.033 Uiso 1 1 calc R U . . .
H17C H 0.867 0.6611 0.0628 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3950(2) 0.83044(12) 0.25820(9) 0.0255(5) Uani 1 1 d . . . . .
H18 H 0.3296 0.7976 0.2401 0.031 Uiso 1 1 calc R U . . .
C19 C 0.3722(2) 0.90285(13) 0.24965(10) 0.0279(5) Uani 1 1 d . . . . .
H19 H 0.2924 0.9192 0.2264 0.033 Uiso 1 1 calc R U . . .
C20 C 0.4672(2) 0.95111(12) 0.27536(9) 0.0258(5) Uani 1 1 d . . . . .
H20 H 0.4548 1.0011 0.2697 0.031 Uiso 1 1 calc R U . . .
C21 C 0.5809(2) 0.92500(12) 0.30961(9) 0.0223(5) Uani 1 1 d . . . . .
H21 H 0.6477 0.957 0.3279 0.027 Uiso 1 1 calc R U . . .
C22 C 0.5963(2) 0.85123(11) 0.31701(8) 0.0177(4) Uani 1 1 d . . . . .
C23 C 0.7092(2) 0.81742(11) 0.35520(8) 0.0174(4) Uani 1 1 d . . . . .
C24 C 0.8148(2) 0.85718(12) 0.38453(9) 0.0231(5) Uani 1 1 d . . . . .
H24 H 0.8182 0.9076 0.3799 0.028 Uiso 1 1 calc R U . . .
C25 C 0.9151(2) 0.82244(13) 0.42059(9) 0.0271(5) Uani 1 1 d . . . . .
H25 H 0.9882 0.8487 0.441 0.033 Uiso 1 1 calc R U . . .
C26 C 0.9073(2) 0.74909(13) 0.42641(9) 0.0265(5) Uani 1 1 d . . . . .
H26 H 0.9743 0.7242 0.4513 0.032 Uiso 1 1 calc R U . . .
C27 C 0.8005(2) 0.71248(12) 0.39550(9) 0.0221(4) Uani 1 1 d . . . . .
H27 H 0.796 0.662 0.3994 0.027 Uiso 1 1 calc R U . . .
C28 C 0.3184(2) 0.75788(11) -0.01814(8) 0.0185(4) Uani 1 1 d . . . . .
C29 C 0.3921(2) 0.72858(12) -0.05907(9) 0.0237(5) Uani 1 1 d . . . . .
H29 H 0.4388 0.7601 -0.0803 0.028 Uiso 1 1 calc R U . . .
C30 C 0.3971(2) 0.65747(12) -0.06841(9) 0.0254(5) Uani 1 1 d . . . . .
H30 H 0.4487 0.6404 -0.0955 0.03 Uiso 1 1 calc R U . . .
C31 C 0.3271(2) 0.60702(11) -0.03874(9) 0.0209(4) Uani 1 1 d . . . . .
C32 C 0.3346(2) 0.53260(12) -0.04782(9) 0.0282(5) Uani 1 1 d . . . . .
H32 H 0.3886 0.5149 -0.0739 0.034 Uiso 1 1 calc R U . . .
C33 C 0.2649(2) 0.48578(12) -0.01945(10) 0.0297(5) Uani 1 1 d . . . . .
H33 H 0.2714 0.4357 -0.0255 0.036 Uiso 1 1 calc R U . . .
C34 C 0.1838(2) 0.51167(12) 0.01853(9) 0.0260(5) Uani 1 1 d . . . . .
H34 H 0.1333 0.479 0.0373 0.031 Uiso 1 1 calc R U . . .
C35 C 0.1764(2) 0.58398(11) 0.02894(8) 0.0190(4) Uani 1 1 d . . . . .
H35 H 0.1212 0.6006 0.0549 0.023 Uiso 1 1 calc R U . . .
C36 C 0.2505(2) 0.63365(11) 0.00121(8) 0.0183(4) Uani 1 1 d . . . . .
C37 C 0.2488(2) 0.70931(11) 0.01272(8) 0.0169(4) Uani 1 1 d . . . . .
C38 C 0.1268(2) 0.80543(11) 0.12113(8) 0.0170(4) Uani 1 1 d . . . . .
C39 C 0.0937(2) 0.87797(11) 0.12813(8) 0.0175(4) Uani 1 1 d . . . . .
C40 C 0.0328(2) 0.89634(11) 0.17451(9) 0.0201(4) Uani 1 1 d . . . . .
H40 H 0.0036 0.9442 0.1788 0.024 Uiso 1 1 calc R U . . .
C41 C 0.0149(2) 0.84532(11) 0.21413(9) 0.0204(4) Uani 1 1 d . . . . .
C42 C 0.0576(2) 0.77431(11) 0.20775(9) 0.0192(4) Uani 1 1 d . . . . .
H42 H 0.0492 0.74 0.2357 0.023 Uiso 1 1 calc R U . . .
C43 C 0.1115(2) 0.75402(11) 0.16123(8) 0.0180(4) Uani 1 1 d . . . . .
H43 H 0.1378 0.7058 0.1566 0.022 Uiso 1 1 calc R U . . .
C44 C -0.0499(2) 0.86441(13) 0.26411(9) 0.0278(5) Uani 1 1 d . . . . .
H44A H -0.0773 0.9149 0.262 0.042 Uiso 1 1 calc R U . . .
H44B H 0.016 0.8564 0.2977 0.042 Uiso 1 1 calc R U . . .
H44C H -0.1307 0.8343 0.2651 0.042 Uiso 1 1 calc R U . . .
C45 C 0.4742(2) 0.85996(11) 0.12085(9) 0.0212(4) Uani 1 1 d . . . . .
H45 H 0.4432 0.8118 0.1211 0.025 Uiso 1 1 calc R U . . .
C46 C 0.5906(2) 0.87904(12) 0.15683(9) 0.0233(5) Uani 1 1 d . . . . .
H46 H 0.6383 0.8446 0.1811 0.028 Uiso 1 1 calc R U . . .
C47 C 0.6361(2) 0.94903(12) 0.15683(9) 0.0245(5) Uani 1 1 d . . . . .
H47 H 0.7144 0.9639 0.1816 0.029 Uiso 1 1 calc R U . . .
C48 C 0.5650(2) 0.99728(11) 0.11981(9) 0.0228(5) Uani 1 1 d . . . . .
H48 H 0.5947 1.0456 0.1187 0.027 Uiso 1 1 calc R U . . .
C49 C 0.4500(2) 0.97407(11) 0.08440(8) 0.0178(4) Uani 1 1 d . . . . .
C50 C 0.3730(2) 1.02071(10) 0.04176(8) 0.0173(4) Uani 1 1 d . . . . .
C51 C 0.4129(2) 1.09036(11) 0.03233(9) 0.0211(4) Uani 1 1 d . . . . .
H51 H 0.491 1.1105 0.0544 0.025 Uiso 1 1 calc R U . . .
C52 C 0.3379(2) 1.13020(11) -0.00944(9) 0.0227(5) Uani 1 1 d . . . . .
H52 H 0.3651 1.1775 -0.017 0.027 Uiso 1 1 calc R U . . .
C53 C 0.2233(2) 1.10026(11) -0.03985(9) 0.0238(5) Uani 1 1 d . . . . .
H53 H 0.1691 1.1271 -0.0681 0.029 Uiso 1 1 calc R U . . .
C54 C 0.1880(2) 1.03084(11) -0.02896(9) 0.0212(4) Uani 1 1 d . . . . .
H54 H 0.1089 1.0105 -0.0502 0.025 Uiso 1 1 calc R U . . .
N1 N 0.33866(17) 0.62440(9) 0.21185(7) 0.0196(4) Uani 1 1 d . . . . .
N2 N 0.45640(17) 0.65416(9) 0.22395(7) 0.0187(4) Uani 1 1 d . . . . .
N3 N 0.50506(17) 0.80432(9) 0.29077(7) 0.0199(4) Uani 1 1 d . . . . .
N4 N 0.70249(17) 0.74562(9) 0.36012(7) 0.0182(4) Uani 1 1 d . . . . .
N5 N 0.19047(16) 0.72626(9) 0.05832(7) 0.0172(4) Uani 1 1 d . . . . .
N6 N 0.17544(17) 0.79250(9) 0.07083(7) 0.0169(3) Uani 1 1 d . . . . .
N7 N 0.40341(17) 0.90636(9) 0.08566(7) 0.0181(4) Uani 1 1 d . . . . .
N8 N 0.26174(17) 0.99086(9) 0.01073(7) 0.0179(4) Uani 1 1 d . . . . .
O1 O 0.39418(15) 0.67831(8) 0.32706(6) 0.0236(3) Uani 1 1 d . . . . .
O2 O 0.69321(15) 0.71681(8) 0.24782(6) 0.0236(3) Uani 1 1 d . . . . .
O3 O 0.63451(16) 0.60879(8) 0.32162(6) 0.0255(3) Uani 1 1 d . . . . .
O4 O 0.32302(15) 0.82668(7) -0.01014(6) 0.0214(3) Uani 1 1 d . . . . .
O5 O 0.11928(15) 0.92576(7) 0.09098(6) 0.0206(3) Uani 1 1 d . . . . .
O6 O 0.06977(15) 0.88605(8) -0.02121(6) 0.0242(3) Uani 1 1 d . . . . .
V1 V 0.57032(4) 0.68400(2) 0.29864(2) 0.01831(9) Uani 1 1 d . . . . .
V2 V 0.19770(4) 0.88576(2) 0.02793(2) 0.01748(9) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O1 1.306(2) . ?
C1 C10 1.423(3) . ?
C1 C2 1.432(3) . ?
C2 C3 1.362(3) . ?
C2 H2 0.95 . ?
C3 C4 1.426(3) . ?
C3 H3 0.95 . ?
C4 C9 1.415(3) . ?
C4 C5 1.419(3) . ?
C5 C6 1.369(3) . ?
C5 H5 0.95 . ?
C6 C7 1.401(3) . ?
C6 H6 0.95 . ?
C7 C8 1.380(3) . ?
C7 H7 0.95 . ?
C8 C9 1.414(3) . ?
C8 H8 0.95 . ?
C9 C10 1.452(3) . ?
C10 N1 1.373(3) . ?
C11 C16 1.396(3) . ?
C11 C12 1.406(3) . ?
C11 N2 1.413(3) . ?
C12 O2 1.332(2) . ?
C12 C13 1.399(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.95 . ?
C14 C15 1.402(3) . ?
C14 C17 1.509(3) . ?
C15 C16 1.384(3) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 N3 1.339(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.95 . ?
C19 C20 1.383(3) . ?
C19 H19 0.95 . ?
C20 C21 1.385(3) . ?
C20 H20 0.95 . ?
C21 C22 1.395(3) . ?
C21 H21 0.95 . ?
C22 N3 1.348(3) . ?
C22 C23 1.484(3) . ?
C23 N4 1.349(3) . ?
C23 C24 1.389(3) . ?
C24 C25 1.384(3) . ?
C24 H24 0.95 . ?
C25 C26 1.381(3) . ?
C25 H25 0.95 . ?
C26 C27 1.383(3) . ?
C26 H26 0.95 . ?
C27 N4 1.347(3) . ?
C27 H27 0.95 . ?
C28 O4 1.300(2) . ?
C28 C37 1.422(3) . ?
C28 C29 1.433(3) . ?
C29 C30 1.350(3) . ?
C29 H29 0.95 . ?
C30 C31 1.430(3) . ?
C30 H30 0.95 . ?
C31 C32 1.411(3) . ?
C31 C36 1.414(3) . ?
C32 C33 1.366(3) . ?
C32 H32 0.95 . ?
C33 C34 1.402(3) . ?
C33 H33 0.95 . ?
C34 C35 1.378(3) . ?
C34 H34 0.95 . ?
C35 C36 1.417(3) . ?
C35 H35 0.95 . ?
C36 C37 1.442(3) . ?
C37 N5 1.368(3) . ?
C38 C43 1.397(3) . ?
C38 N6 1.408(3) . ?
C38 C39 1.410(3) . ?
C39 O5 1.325(2) . ?
C39 C40 1.405(3) . ?
C40 C41 1.389(3) . ?
C40 H40 0.95 . ?
C41 C42 1.408(3) . ?
C41 C44 1.506(3) . ?
C42 C43 1.380(3) . ?
C42 H42 0.95 . ?
C43 H43 0.95 . ?
C44 H44A 0.98 . ?
C44 H44B 0.98 . ?
C44 H44C 0.98 . ?
C45 N7 1.341(3) . ?
C45 C46 1.385(3) . ?
C45 H45 0.95 . ?
C46 C47 1.383(3) . ?
C46 H46 0.95 . ?
C47 C48 1.390(3) . ?
C47 H47 0.95 . ?
C48 C49 1.390(3) . ?
C48 H48 0.95 . ?
C49 N7 1.348(3) . ?
C49 C50 1.478(3) . ?
C50 N8 1.358(3) . ?
C50 C51 1.389(3) . ?
C51 C52 1.384(3) . ?
C51 H51 0.95 . ?
C52 C53 1.376(3) . ?
C52 H52 0.95 . ?
C53 C54 1.379(3) . ?
C53 H53 0.95 . ?
C54 N8 1.348(3) . ?
C54 H54 0.95 . ?
N1 N2 1.284(2) . ?
N2 V1 2.0711(18) . ?
N3 V1 2.3380(18) . ?
N4 V1 2.1669(17) . ?
N5 N6 1.289(2) . ?
N6 V2 2.0622(17) . ?
N7 V2 2.3253(17) . ?
N8 V2 2.1242(17) . ?
O1 V1 1.9735(15) . ?
O2 V1 1.9632(15) . ?
O3 V1 1.6075(15) . ?
O4 V2 1.9924(15) . ?
O5 V2 1.9742(15) . ?
O6 V2 1.6069(15) . ?

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 C1 C10 123.86(18) . . ?
O1 C1 C2 117.81(19) . . ?
C10 C1 C2 118.32(19) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3 119 . . ?
C4 C3 H3 119 . . ?
C9 C4 C5 119.4(2) . . ?
C9 C4 C3 118.87(19) . . ?
C5 C4 C3 121.75(19) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.6(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.7(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 118.43(19) . . ?
C8 C9 C10 122.18(19) . . ?
C4 C9 C10 119.34(19) . . ?
N1 C10 C1 126.26(18) . . ?
N1 C10 C9 113.32(18) . . ?
C1 C10 C9 120.15(18) . . ?
C16 C11 C12 120.78(19) . . ?
C16 C11 N2 126.91(19) . . ?
C12 C11 N2 112.30(18) . . ?
O2 C12 C13 122.10(18) . . ?
O2 C12 C11 119.56(18) . . ?
C13 C12 C11 118.32(19) . . ?
C14 C13 C12 121.38(19) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 119.20(19) . . ?
C13 C14 C17 119.38(19) . . ?
C15 C14 C17 121.42(19) . . ?
C16 C15 C14 120.63(19) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 119.66(19) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 C19 123.1(2) . . ?
N3 C18 H18 118.4 . . ?
C19 C18 H18 118.4 . . ?
C18 C19 C20 119.0(2) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C19 C20 C21 118.6(2) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C20 C21 C22 119.3(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
N3 C22 C21 121.92(19) . . ?
N3 C22 C23 114.08(18) . . ?
C21 C22 C23 123.97(18) . . ?
N4 C23 C24 121.91(19) . . ?
N4 C23 C22 115.92(17) . . ?
C24 C23 C22 122.17(19) . . ?
C25 C24 C23 119.2(2) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 119.0(2) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C27 119.0(2) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
N4 C27 C26 122.6(2) . . ?
N4 C27 H27 118.7 . . ?
C26 C27 H27 118.7 . . ?
O4 C28 C37 124.03(19) . . ?
O4 C28 C29 118.22(18) . . ?
C37 C28 C29 117.71(19) . . ?
C30 C29 C28 122.0(2) . . ?
C30 C29 H29 119 . . ?
C28 C29 H29 119 . . ?
C29 C30 C31 122.0(2) . . ?
C29 C30 H30 119 . . ?
C31 C30 H30 119 . . ?
C32 C31 C36 120.1(2) . . ?
C32 C31 C30 121.9(2) . . ?
C36 C31 C30 118.01(19) . . ?
C33 C32 C31 120.6(2) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C34 119.9(2) . . ?
C32 C33 H33 120 . . ?
C34 C33 H33 120 . . ?
C35 C34 C33 120.8(2) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C34 C35 C36 120.5(2) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C31 C36 C35 118.05(19) . . ?
C31 C36 C37 120.19(19) . . ?
C35 C36 C37 121.76(19) . . ?
N5 C37 C28 125.62(18) . . ?
N5 C37 C36 113.88(17) . . ?
C28 C37 C36 120.06(18) . . ?
C43 C38 N6 125.66(18) . . ?
C43 C38 C39 121.58(19) . . ?
N6 C38 C39 112.76(17) . . ?
O5 C39 C40 122.57(18) . . ?
O5 C39 C38 119.51(18) . . ?
C40 C39 C38 117.91(18) . . ?
C41 C40 C39 120.72(19) . . ?
C41 C40 H40 119.6 . . ?
C39 C40 H40 119.6 . . ?
C40 C41 C42 119.80(19) . . ?
C40 C41 C44 121.22(19) . . ?
C42 C41 C44 118.99(19) . . ?
C43 C42 C41 120.65(19) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C42 C43 C38 119.08(19) . . ?
C42 C43 H43 120.5 . . ?
C38 C43 H43 120.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N7 C45 C46 122.94(19) . . ?
N7 C45 H45 118.5 . . ?
C46 C45 H45 118.5 . . ?
C47 C46 C45 118.8(2) . . ?
C47 C46 H46 120.6 . . ?
C45 C46 H46 120.6 . . ?
C46 C47 C48 118.7(2) . . ?
C46 C47 H47 120.6 . . ?
C48 C47 H47 120.6 . . ?
C49 C48 C47 119.2(2) . . ?
C49 C48 H48 120.4 . . ?
C47 C48 H48 120.4 . . ?
N7 C49 C48 121.91(19) . . ?
N7 C49 C50 115.34(18) . . ?
C48 C49 C50 122.72(18) . . ?
N8 C50 C51 121.22(19) . . ?
N8 C50 C49 116.03(17) . . ?
C51 C50 C49 122.72(19) . . ?
C52 C51 C50 119.5(2) . . ?
C52 C51 H51 120.3 . . ?
C50 C51 H51 120.3 . . ?
C53 C52 C51 119.00(19) . . ?
C53 C52 H52 120.5 . . ?
C51 C52 H52 120.5 . . ?
C52 C53 C54 119.3(2) . . ?
C52 C53 H53 120.3 . . ?
C54 C53 H53 120.3 . . ?
N8 C54 C53 122.3(2) . . ?
N8 C54 H54 118.8 . . ?
C53 C54 H54 118.8 . . ?
N2 N1 C10 119.83(18) . . ?
N1 N2 C11 115.44(17) . . ?
N1 N2 V1 132.28(14) . . ?
C11 N2 V1 111.97(13) . . ?
C18 N3 C22 118.07(19) . . ?
C18 N3 V1 126.05(14) . . ?
C22 N3 V1 115.43(13) . . ?
C27 N4 C23 118.28(18) . . ?
C27 N4 V1 120.03(14) . . ?
C23 N4 V1 119.92(13) . . ?
N6 N5 C37 119.59(17) . . ?
N5 N6 C38 116.04(16) . . ?
N5 N6 V2 131.71(14) . . ?
C38 N6 V2 112.10(12) . . ?
C45 N7 C49 118.29(18) . . ?
C45 N7 V2 127.30(14) . . ?
C49 N7 V2 114.33(13) . . ?
C54 N8 C50 118.60(17) . . ?
C54 N8 V2 120.64(14) . . ?
C50 N8 V2 120.64(13) . . ?
C1 O1 V1 129.62(13) . . ?
C12 O2 V1 114.78(13) . . ?
C28 O4 V2 127.43(13) . . ?
C39 O5 V2 114.74(12) . . ?
O3 V1 O2 104.14(7) . . ?
O3 V1 O1 98.79(7) . . ?
O2 V1 O1 154.65(7) . . ?
O3 V1 N2 101.89(7) . . ?
O2 V1 N2 80.34(7) . . ?
O1 V1 N2 84.53(7) . . ?
O3 V1 N4 93.28(7) . . ?
O2 V1 N4 84.66(6) . . ?
O1 V1 N4 104.85(6) . . ?
N2 V1 N4 160.83(7) . . ?
O3 V1 N3 163.39(7) . . ?
O2 V1 N3 80.65(6) . . ?
O1 V1 N3 80.41(6) . . ?
N2 V1 N3 94.57(6) . . ?
N4 V1 N3 71.12(6) . . ?
O6 V2 O5 102.97(7) . . ?
O6 V2 O4 97.33(7) . . ?
O5 V2 O4 156.93(6) . . ?
O6 V2 N6 104.50(7) . . ?
O5 V2 N6 80.67(6) . . ?
O4 V2 N6 83.77(6) . . ?
O6 V2 N8 94.21(7) . . ?
O5 V2 N8 88.22(6) . . ?
O4 V2 N8 101.20(6) . . ?
N6 V2 N8 159.94(7) . . ?
O6 V2 N7 165.97(7) . . ?
O5 V2 N7 82.80(6) . . ?
O4 V2 N7 80.00(6) . . ?
N6 V2 N7 88.98(6) . . ?
N8 V2 N7 73.00(6) . . ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1907848'
loop_
_audit_author_name
_audit_author_address
'Werner Kaminsky'
;University of Washington
United States of America
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-07-12 downloaded from the CCDC.
;

_audit_creation_date             2018-09-18T10:48:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C26 H17 N5 O5 V'
_chemical_formula_sum            'C26 H17 N5 O5 V'
_chemical_formula_weight         530.39

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4764(7)
_cell_length_b                   16.7531(13)
_cell_length_c                   16.4889(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.846(4)
_cell_angle_gamma                90
_cell_volume                     2273.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9869
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      26.37
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            gold
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.55
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1084

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.981

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      -0.014358
_diffrn_orient_matrix_ub_12      -0.042365
_diffrn_orient_matrix_ub_13      -0.043884
_diffrn_orient_matrix_ub_21      0.056205
_diffrn_orient_matrix_ub_22      0.034591
_diffrn_orient_matrix_ub_23      -0.033778
_diffrn_orient_matrix_ub_31      0.106763
_diffrn_orient_matrix_ub_32      -0.023908
_diffrn_orient_matrix_ub_33      0.028892
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_number            11204
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.759
_diffrn_reflns_theta_max         28.497
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_Friedel_coverage         0
_reflns_number_total             5716
_reflns_number_gt                4044
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+0.9966P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5716
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.45
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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 0.4304(2) 0.21462(12) 0.81815(12) 0.0303(4) Uani 1 1 d . . . . .
C2 C 0.5604(2) 0.19990(13) 0.77833(12) 0.0362(5) Uani 1 1 d . . . . .
H2 H 0.5729 0.1481 0.7574 0.043 Uiso 1 1 calc R U . . .
C3 C 0.6657(2) 0.25823(14) 0.76995(12) 0.0375(5) Uani 1 1 d . . . . .
H3 H 0.7499 0.2462 0.7428 0.045 Uiso 1 1 calc R U . . .
C4 C 0.6548(2) 0.33731(13) 0.80043(12) 0.0349(5) Uani 1 1 d . . . . .
C5 C 0.7636(2) 0.39829(16) 0.79017(13) 0.0451(6) Uani 1 1 d . . . . .
H5 H 0.8492 0.3863 0.764 0.054 Uiso 1 1 calc R U . . .
C6 C 0.7475(3) 0.47466(16) 0.81752(14) 0.0503(6) Uani 1 1 d . . . . .
H6 H 0.8195 0.5154 0.8087 0.06 Uiso 1 1 calc R U . . .
C7 C 0.6257(3) 0.49209(14) 0.85803(13) 0.0429(5) Uani 1 1 d . . . . .
H7 H 0.6152 0.5448 0.8774 0.052 Uiso 1 1 calc R U . . .
C8 C 0.5198(2) 0.43342(12) 0.87036(12) 0.0352(5) Uani 1 1 d . . . . .
H8 H 0.4384 0.446 0.8992 0.042 Uiso 1 1 calc R U . . .
C9 C 0.5303(2) 0.35525(12) 0.84100(12) 0.0308(4) Uani 1 1 d . . . . .
C10 C 0.4152(2) 0.29294(11) 0.84990(11) 0.0283(4) Uani 1 1 d . . . . .
C11 C 0.0806(2) 0.29957(10) 0.94525(11) 0.0245(4) Uani 1 1 d . . . . .
C12 C -0.0464(2) 0.24601(10) 0.94757(11) 0.0231(4) Uani 1 1 d . . . . .
C13 C -0.1652(2) 0.26931(11) 0.98881(11) 0.0250(4) Uani 1 1 d . . . . .
H13 H -0.2536 0.2351 0.9906 0.03 Uiso 1 1 calc R U . . .
C14 C -0.1509(2) 0.34321(11) 1.02680(11) 0.0269(4) Uani 1 1 d . . . . .
C15 C -0.0245(2) 0.39561(11) 1.02611(12) 0.0324(4) Uani 1 1 d . . . . .
H15 H -0.0183 0.4457 1.0537 0.039 Uiso 1 1 calc R U . . .
C16 C 0.0922(2) 0.37366(11) 0.98462(12) 0.0318(4) Uani 1 1 d . . . . .
H16 H 0.1794 0.4087 0.9829 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3802(2) 0.13782(11) 1.02487(11) 0.0265(4) Uani 1 1 d . . . . .
H17 H 0.4031 0.1924 1.0171 0.032 Uiso 1 1 calc R U . . .
C18 C 0.4699(2) 0.09883(12) 1.09478(12) 0.0315(4) Uani 1 1 d . . . . .
H18 H 0.5534 0.1258 1.1338 0.038 Uiso 1 1 calc R U . . .
C19 C 0.4351(2) 0.01952(12) 1.10650(12) 0.0340(5) Uani 1 1 d . . . . .
H19 H 0.4944 -0.0088 1.154 0.041 Uiso 1 1 calc R U . . .
C20 C 0.3133(2) -0.01802(11) 1.04845(11) 0.0300(4) Uani 1 1 d . . . . .
H20 H 0.2867 -0.0722 1.0559 0.036 Uiso 1 1 calc R U . . .
C21 C 0.2303(2) 0.02444(10) 0.97898(11) 0.0223(4) Uani 1 1 d . . . . .
C22 C 0.1036(2) -0.01032(10) 0.91079(11) 0.0245(4) Uani 1 1 d . . . . .
C23 C 0.0432(2) -0.08718(11) 0.91394(13) 0.0332(4) Uani 1 1 d . . . . .
H23 H 0.0826 -0.1198 0.9616 0.04 Uiso 1 1 calc R U . . .
C24 C -0.0745(2) -0.11577(13) 0.84721(15) 0.0429(6) Uani 1 1 d . . . . .
H24 H -0.1149 -0.1686 0.848 0.051 Uiso 1 1 calc R U . . .
C25 C -0.1320(2) -0.06691(13) 0.77989(15) 0.0437(6) Uani 1 1 d . . . . .
H25 H -0.2138 -0.0851 0.7336 0.052 Uiso 1 1 calc R U . . .
C26 C -0.0691(2) 0.00913(12) 0.78047(13) 0.0348(5) Uani 1 1 d . . . . .
H26 H -0.1104 0.043 0.734 0.042 Uiso 1 1 calc R U . . .
N1 N 0.30315(17) 0.31674(9) 0.89110(9) 0.0268(3) Uani 1 1 d . . . . .
N2 N 0.18619(17) 0.26954(9) 0.89799(9) 0.0253(3) Uani 1 1 d . . . . .
N3 N 0.26256(16) 0.10201(8) 0.96778(9) 0.0218(3) Uani 1 1 d . . . . .
N4 N 0.04793(17) 0.03743(9) 0.84390(9) 0.0256(3) Uani 1 1 d . . . . .
N5 N -0.2786(2) 0.36695(10) 1.06817(10) 0.0333(4) Uani 1 1 d . . . . .
O1 O 0.33552(16) 0.15564(7) 0.82509(8) 0.0326(3) Uani 1 1 d . . . . .
O2 O -0.05064(14) 0.17552(7) 0.91077(8) 0.0257(3) Uani 1 1 d . . . . .
O3 O 0.01813(17) 0.17821(8) 0.75196(8) 0.0367(3) Uani 1 1 d . . . . .
O4 O -0.38825(19) 0.31960(9) 1.07057(10) 0.0453(4) Uani 1 1 d . . . . .
O5 O -0.27068(19) 0.43454(8) 1.09848(9) 0.0430(4) Uani 1 1 d . . . . .
V1 V 0.11477(4) 0.15998(2) 0.84625(2) 0.02494(9) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O1 1.296(2) . ?
C1 C10 1.430(3) . ?
C1 C2 1.433(3) . ?
C2 C3 1.353(3) . ?
C2 H2 0.95 . ?
C3 C4 1.428(3) . ?
C3 H3 0.95 . ?
C4 C9 1.410(3) . ?
C4 C5 1.414(3) . ?
C5 C6 1.374(4) . ?
C5 H5 0.95 . ?
C6 C7 1.389(3) . ?
C6 H6 0.95 . ?
C7 C8 1.378(3) . ?
C7 H7 0.95 . ?
C8 C9 1.407(3) . ?
C8 H8 0.95 . ?
C9 C10 1.460(3) . ?
C10 N1 1.353(2) . ?
C11 C16 1.393(3) . ?
C11 C12 1.409(2) . ?
C11 N2 1.412(2) . ?
C12 O2 1.324(2) . ?
C12 C13 1.399(2) . ?
C13 C14 1.380(2) . ?
C13 H13 0.95 . ?
C14 C15 1.387(3) . ?
C14 N5 1.466(2) . ?
C15 C16 1.380(3) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 N3 1.338(2) . ?
C17 C18 1.383(2) . ?
C17 H17 0.95 . ?
C18 C19 1.385(3) . ?
C18 H18 0.95 . ?
C19 C20 1.380(3) . ?
C19 H19 0.95 . ?
C20 C21 1.388(2) . ?
C20 H20 0.95 . ?
C21 N3 1.350(2) . ?
C21 C22 1.476(2) . ?
C22 N4 1.353(2) . ?
C22 C23 1.391(3) . ?
C23 C24 1.382(3) . ?
C23 H23 0.95 . ?
C24 C25 1.371(3) . ?
C24 H24 0.95 . ?
C25 C26 1.380(3) . ?
C25 H25 0.95 . ?
C26 N4 1.344(2) . ?
C26 H26 0.95 . ?
N1 N2 1.294(2) . ?
N2 V1 2.0533(15) . ?
N3 V1 2.3080(14) . ?
N4 V1 2.1277(15) . ?
N5 O4 1.230(2) . ?
N5 O5 1.233(2) . ?
O1 V1 1.9851(13) . ?
O2 V1 1.9696(13) . ?
O3 V1 1.6036(13) . ?

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 C1 C10 123.71(17) . . ?
O1 C1 C2 118.09(18) . . ?
C10 C1 C2 118.18(18) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 122.30(19) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C9 C4 C5 119.1(2) . . ?
C9 C4 C3 118.93(19) . . ?
C5 C4 C3 122.0(2) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.1(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C4 118.56(19) . . ?
C8 C9 C10 122.14(18) . . ?
C4 C9 C10 119.29(19) . . ?
N1 C10 C1 126.13(17) . . ?
N1 C10 C9 113.96(17) . . ?
C1 C10 C9 119.89(17) . . ?
C16 C11 C12 121.58(17) . . ?
C16 C11 N2 126.24(17) . . ?
C12 C11 N2 112.16(15) . . ?
O2 C12 C13 121.85(16) . . ?
O2 C12 C11 119.52(16) . . ?
C13 C12 C11 118.63(16) . . ?
C14 C13 C12 118.41(17) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 123.25(17) . . ?
C13 C14 N5 117.41(17) . . ?
C15 C14 N5 119.33(16) . . ?
C16 C15 C14 118.81(17) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C11 119.30(18) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
N3 C17 C18 122.87(17) . . ?
N3 C17 H17 118.6 . . ?
C18 C17 H17 118.6 . . ?
C17 C18 C19 118.45(17) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C20 C19 C18 119.30(17) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 119.09(17) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
N3 C21 C20 121.80(16) . . ?
N3 C21 C22 114.19(15) . . ?
C20 C21 C22 124.00(16) . . ?
N4 C22 C23 121.21(17) . . ?
N4 C22 C21 115.85(15) . . ?
C23 C22 C21 122.94(17) . . ?
C24 C23 C22 119.5(2) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C25 C24 C23 119.13(19) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 118.91(19) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
N4 C26 C25 122.9(2) . . ?
N4 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?
N2 N1 C10 120.55(16) . . ?
N1 N2 C11 115.50(15) . . ?
N1 N2 V1 131.73(12) . . ?
C11 N2 V1 112.63(11) . . ?
C17 N3 C21 118.46(15) . . ?
C17 N3 V1 125.47(12) . . ?
C21 N3 V1 116.00(11) . . ?
C26 N4 C22 118.31(16) . . ?
C26 N4 V1 119.89(13) . . ?
C22 N4 V1 121.09(11) . . ?
O4 N5 O5 123.22(17) . . ?
O4 N5 C14 119.20(16) . . ?
O5 N5 C14 117.58(17) . . ?
C1 O1 V1 128.20(11) . . ?
C12 O2 V1 114.86(11) . . ?
O3 V1 O2 103.53(6) . . ?
O3 V1 O1 96.95(7) . . ?
O2 V1 O1 157.30(6) . . ?
O3 V1 N2 105.31(7) . . ?
O2 V1 N2 80.48(5) . . ?
O1 V1 N2 84.79(6) . . ?
O3 V1 N4 95.40(7) . . ?
O2 V1 N4 85.21(5) . . ?
O1 V1 N4 102.68(5) . . ?
N2 V1 N4 157.05(6) . . ?
O3 V1 N3 165.25(6) . . ?
O2 V1 N3 83.99(5) . . ?
O1 V1 N3 78.38(5) . . ?
N2 V1 N3 88.31(5) . . ?
N4 V1 N3 72.34(5) . . ?


#----------------------------------------------------------------------------#
#                   SQUEEZE DETAILS                                          #
#----------------------------------------------------------------------------#

