# 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 2017

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1506828'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2017-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 N4 O5 V'
_chemical_formula_weight         466.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.4417(3)
_cell_length_b                   17.7670(5)
_cell_length_c                   10.7908(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.3670(10)
_cell_angle_gamma                90
_cell_volume                     1962.62(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      28.02

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.551
_shelx_estimated_absorpt_T_min   0.751
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Mo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16585
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.733
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4857
_reflns_number_gt                3424
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0729P)²+1.3445P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4857
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1565
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.2258(3) 0.80653(16) 0.3274(3) 0.0445(6) Uani 1 1 d . . . . .
C3 C 0.1475(3) 0.8711(2) 0.3251(4) 0.0617(9) Uani 1 1 d . . . . .
H3 H 0.1675 0.9065 0.3895 0.074 Uiso 1 1 calc R U . . .
C4 C 0.0422(4) 0.8825(2) 0.2290(4) 0.0726(11) Uani 1 1 d . . . . .
H4 H -0.0082 0.9256 0.2300 0.087 Uiso 1 1 calc R U . . .
C5 C 0.0088(4) 0.8320(3) 0.1310(4) 0.0781(11) Uani 1 1 d . . . . .
H5 H -0.0624 0.8411 0.0660 0.094 Uiso 1 1 calc R U . . .
C6 C 0.0819(4) 0.7691(2) 0.1314(4) 0.0704(10) Uani 1 1 d . . . . .
H6 H 0.0598 0.7348 0.0655 0.084 Uiso 1 1 calc R U . . .
C7 C 0.1904(3) 0.75370(18) 0.2286(3) 0.0483(7) Uani 1 1 d . . . . .
C8 C 0.2647(3) 0.68859(18) 0.2172(3) 0.0489(7) Uani 1 1 d . . . . .
H8 H 0.2377 0.6595 0.1451 0.059 Uiso 1 1 calc R U . . .
C10 C 0.4298(3) 0.59830(16) 0.2690(3) 0.0451(6) Uani 1 1 d . . . . .
C11 C 0.4004(4) 0.5551(2) 0.1616(3) 0.0692(10) Uani 1 1 d . . . . .
H11 H 0.3344 0.5703 0.0953 0.083 Uiso 1 1 calc R U . . .
C12 C 0.4686(5) 0.4888(2) 0.1510(4) 0.0795(12) Uani 1 1 d . . . . .
H12 H 0.4441 0.4594 0.0789 0.095 Uiso 1 1 calc R U . . .
C13 C 0.5681(4) 0.4661(2) 0.2412(4) 0.0684(10) Uani 1 1 d . . . . .
H13 H 0.6129 0.4221 0.2301 0.082 Uiso 1 1 calc R U . . .
C14 C 0.6060(3) 0.50915(17) 0.3543(3) 0.0535(8) Uani 1 1 d . . . . .
C15 C 0.7064(3) 0.48976(19) 0.4550(4) 0.0657(10) Uani 1 1 d . . . . .
H15 H 0.7573 0.4474 0.4495 0.079 Uiso 1 1 calc R U . . .
C16 C 0.7292(3) 0.5322(2) 0.5595(4) 0.0699(11) Uani 1 1 d . . . . .
H16 H 0.7943 0.5186 0.6276 0.084 Uiso 1 1 calc R U . . .
C17 C 0.6546(3) 0.59721(19) 0.5660(3) 0.0591(8) Uani 1 1 d . . . . .
H17 H 0.6720 0.6260 0.6393 0.071 Uiso 1 1 calc R U . . .
C19 C 0.5342(3) 0.57555(15) 0.3665(3) 0.0412(6) Uani 1 1 d . . . . .
C22 C 0.6756(3) 0.80034(16) 0.4515(2) 0.0410(6) Uani 1 1 d . . . . .
C23 C 0.7810(3) 0.8369(2) 0.4145(3) 0.0549(8) Uani 1 1 d . . . . .
H23 H 0.7913 0.8342 0.3310 0.066 Uiso 1 1 calc R U . . .
C24 C 0.8690(3) 0.8768(2) 0.5016(3) 0.0596(8) Uani 1 1 d . . . . .
H24 H 0.9360 0.9033 0.4759 0.072 Uiso 1 1 calc R U . . .
C25 C 0.8583(3) 0.87764(18) 0.6275(3) 0.0524(7) Uani 1 1 d . . . . .
C26 C 0.7592(3) 0.84041(17) 0.6708(3) 0.0466(7) Uani 1 1 d . . . . .
H26 H 0.7549 0.8406 0.7560 0.056 Uiso 1 1 calc R U . . .
C27 C 0.6660(3) 0.80259(14) 0.5821(2) 0.0375(6) Uani 1 1 d . . . . .
N9 N 0.3659(2) 0.66514(13) 0.2962(2) 0.0401(5) Uani 1 1 d . . . . .
N18 N 0.5602(2) 0.61938(13) 0.4720(2) 0.0424(5) Uani 1 1 d . . . . .
N28 N 0.5618(2) 0.76372(13) 0.60684(19) 0.0391(5) Uani 1 1 d . . . . .
H28 H 0.5499 0.7607 0.6833 0.047 Uiso 1 1 calc R U . . .
N29 N 0.9582(3) 0.91611(19) 0.7184(3) 0.0728(9) Uani 1 1 d . . . . .
O1 O 0.3303(2) 0.79993(11) 0.4156(2) 0.0538(5) Uani 1 1 d . . . . .
O21 O 0.5843(2) 0.76364(12) 0.37747(16) 0.0460(5) Uani 1 1 d . . . . .
O30 O 0.9480(3) 0.9185(2) 0.8287(3) 0.1080(12) Uani 1 1 d . . . . .
O31 O 1.0495(3) 0.94575(19) 0.6798(3) 0.0938(10) Uani 1 1 d . . . . .
O40 O 0.3590(2) 0.67654(13) 0.5660(2) 0.0537(5) Uani 1 1 d . . . . .
V1 V 0.44164(5) 0.71574(3) 0.47448(4) 0.03825(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O1 1.304(4) . ?
C2 C3 1.406(4) . ?
C2 C7 1.414(4) . ?
C3 C4 1.370(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.354(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.411(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.411(5) . ?
C8 N9 1.289(4) . ?
C8 H8 0.9300 . ?
C10 C11 1.373(4) . ?
C10 C19 1.417(4) . ?
C10 N9 1.421(4) . ?
C11 C12 1.393(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.339(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.429(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.396(5) . ?
C14 C19 1.418(4) . ?
C15 C16 1.338(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.403(5) . ?
C16 H16 0.9300 . ?
C17 N18 1.327(4) . ?
C17 H17 0.9300 . ?
C19 N18 1.362(4) . ?
C22 O21 1.293(3) . ?
C22 C23 1.402(4) . ?
C22 C27 1.433(4) . ?
C23 C24 1.375(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.385(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(4) . ?
C25 N29 1.454(4) . ?
C26 C27 1.395(4) . ?
C26 H26 0.9300 . ?
C27 N28 1.359(4) . ?
N9 V1 2.130(2) . ?
N18 V1 2.116(2) . ?
N28 V1 1.907(2) . ?
N28 H28 0.8600 . ?
N29 O30 1.217(4) . ?
N29 O31 1.230(4) . ?
O1 V1 1.924(2) . ?
O21 V1 2.1576(19) . ?
O40 V1 1.594(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 C3 119.1(3) . . ?
O1 C2 C7 123.2(3) . . ?
C3 C2 C7 117.6(3) . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 121.9(4) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C7 122.1(4) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C8 117.9(3) . . ?
C6 C7 C2 119.0(3) . . ?
C8 C7 C2 122.9(3) . . ?
N9 C8 C7 126.9(3) . . ?
N9 C8 H8 116.6 . . ?
C7 C8 H8 116.6 . . ?
C11 C10 C19 118.6(3) . . ?
C11 C10 N9 127.3(3) . . ?
C19 C10 N9 114.1(2) . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 122.1(4) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C19 117.6(3) . . ?
C15 C14 C13 124.9(3) . . ?
C19 C14 C13 117.5(3) . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
N18 C17 C16 122.8(3) . . ?
N18 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
N18 C19 C10 117.1(2) . . ?
N18 C19 C14 122.1(3) . . ?
C10 C19 C14 120.8(3) . . ?
O21 C22 C23 125.6(3) . . ?
O21 C22 C27 115.9(2) . . ?
C23 C22 C27 118.5(3) . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 122.4(3) . . ?
C26 C25 N29 118.8(3) . . ?
C24 C25 N29 118.7(3) . . ?
C25 C26 C27 117.8(3) . . ?
C25 C26 H26 121.1 . . ?
C27 C26 H26 121.1 . . ?
N28 C27 C26 126.0(2) . . ?
N28 C27 C22 113.1(2) . . ?
C26 C27 C22 120.9(3) . . ?
C8 N9 C10 119.4(2) . . ?
C8 N9 V1 124.8(2) . . ?
C10 N9 V1 115.71(18) . . ?
C17 N18 C19 117.7(3) . . ?
C17 N18 V1 125.4(2) . . ?
C19 N18 V1 116.89(19) . . ?
C27 N28 V1 120.96(17) . . ?
C27 N28 H28 119.5 . . ?
V1 N28 H28 119.5 . . ?
O30 N29 O31 122.6(3) . . ?
O30 N29 C25 119.1(3) . . ?
O31 N29 C25 118.3(3) . . ?
C2 O1 V1 132.45(19) . . ?
C22 O21 V1 113.22(16) . . ?
O40 V1 N28 95.04(10) . . ?
O40 V1 O1 100.28(11) . . ?
N28 V1 O1 99.51(9) . . ?
O40 V1 N18 92.52(10) . . ?
N28 V1 N18 94.06(9) . . ?
O1 V1 N18 160.37(10) . . ?
O40 V1 N9 103.03(10) . . ?
N28 V1 N9 159.70(9) . . ?
O1 V1 N9 86.41(9) . . ?
N18 V1 N9 76.18(9) . . ?
O40 V1 O21 169.39(10) . . ?
N28 V1 O21 76.80(8) . . ?
O1 V1 O21 87.89(9) . . ?
N18 V1 O21 81.45(9) . . ?
N9 V1 O21 84.09(8) . . ?

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.067

_shelxl_version_number           2014/6

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

data_7257
_database_code_depnum_ccdc_archive 'CCDC 1506827'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2017-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_audit_creation_date             2011-02-17
_audit_block_code                WGT-PG-500-07
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H31 N2 O4 V'
_chemical_formula_sum            'C30 H31 N2 O4 V'
_chemical_formula_weight         534.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   15.194(2)
_cell_length_b                   19.427(2)
_cell_length_c                   9.3109(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.744(6)
_cell_angle_gamma                90
_cell_volume                     2631.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    88604
_cell_measurement_theta_min      2.7947
_cell_measurement_theta_max      33.0998

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.415
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_absorpt_correction_T_min  0.90851
_exptl_absorpt_correction_T_max  0.93894

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_detector_area_resol_mean 18.02
_diffrn_reflns_number            82107
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.800
_diffrn_reflns_theta_max         33.172
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             10053
_reflns_number_gt                8523
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_cell_refinement       'DENZO (Bruker AXS, 2006)'
_computing_data_reduction        'DENZO (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP, Version 5.03, Siemens 1994)'
_computing_publication_material  'XCIF, Version 6.12, Bruker Nonius 2001'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0395P)²+1.1056P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10053
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.36583(2) 0.38932(2) 0.56681(2) 0.01418(4) Uani 1 1 d . . . . .
O40 O 0.43438(5) 0.37804(4) 0.46350(8) 0.01793(13) Uani 1 1 d . . . . .
O1 O 0.26515(5) 0.33093(4) 0.46176(9) 0.01983(14) Uani 1 1 d . . . . .
C2 C 0.24319(6) 0.26676(5) 0.47771(11) 0.01673(16) Uani 1 1 d . . . . .
C3 C 0.16987(7) 0.23631(5) 0.36535(12) 0.02123(18) Uani 1 1 d . . . . .
H3 H 0.1399 0.2619 0.2780 0.025 Uiso 1 1 calc R U . . .
C4 C 0.14161(7) 0.17000(5) 0.38151(13) 0.02314(19) Uani 1 1 d . . . . .
H4 H 0.0926 0.1505 0.3048 0.028 Uiso 1 1 calc R U . . .
C5 C 0.18421(8) 0.13075(5) 0.50989(13) 0.02232(19) Uani 1 1 d . . . . .
H5 H 0.1631 0.0856 0.5211 0.027 Uiso 1 1 calc R U . . .
C6 C 0.25671(7) 0.15864(5) 0.61883(12) 0.01972(17) Uani 1 1 d . . . . .
H6 H 0.2859 0.1321 0.7051 0.024 Uiso 1 1 calc R U . . .
C7 C 0.28876(6) 0.22634(5) 0.60477(11) 0.01671(16) Uani 1 1 d . . . . .
C8 C 0.36432(7) 0.25124(5) 0.72394(11) 0.01711(16) Uani 1 1 d . . . . .
H8 H 0.3876 0.2213 0.8068 0.021 Uiso 1 1 calc R U . . .
N9 N 0.40452(5) 0.31127(4) 0.72994(9) 0.01589(14) Uani 1 1 d . . . . .
C10 C 0.47820(7) 0.32898(5) 0.85889(11) 0.01723(16) Uani 1 1 d . . . . .
C11 C 0.51995(8) 0.28657(5) 0.97880(13) 0.0235(2) Uani 1 1 d . . . . .
H11 H 0.4993 0.2405 0.9811 0.028 Uiso 1 1 calc R U . . .
C12 C 0.59349(8) 0.31185(6) 1.09808(13) 0.0271(2) Uani 1 1 d . . . . .
H12 H 0.6214 0.2822 1.1796 0.033 Uiso 1 1 calc R U . . .
C13 C 0.62573(8) 0.37807(6) 1.09941(13) 0.0239(2) Uani 1 1 d . . . . .
H13 H 0.6752 0.3937 1.1807 0.029 Uiso 1 1 calc R U . . .
C14 C 0.58442(7) 0.42282(5) 0.97832(12) 0.01876(17) Uani 1 1 d . . . . .
C15 C 0.61181(7) 0.49249(5) 0.97023(12) 0.02096(18) Uani 1 1 d . . . . .
H15 H 0.6603 0.5116 1.0486 0.025 Uiso 1 1 calc R U . . .
C16 C 0.56759(7) 0.53166(5) 0.84830(12) 0.02161(19) Uani 1 1 d . . . . .
H16 H 0.5854 0.5781 0.8414 0.026 Uiso 1 1 calc R U . . .
C17 C 0.49558(7) 0.50260(5) 0.73324(12) 0.01951(17) Uani 1 1 d . . . . .
H17 H 0.4661 0.5301 0.6487 0.023 Uiso 1 1 calc R U . . .
N18 N 0.46752(6) 0.43819(4) 0.73869(10) 0.01627(14) Uani 1 1 d . . . . .
C19 C 0.51062(6) 0.39776(5) 0.85928(11) 0.01631(16) Uani 1 1 d . . . . .
O21 O 0.31443(5) 0.47358(3) 0.47166(8) 0.01667(13) Uani 1 1 d . . . . .
C22 C 0.25443(6) 0.50790(5) 0.52173(11) 0.01670(16) Uani 1 1 d . . . . .
C23 C 0.21193(7) 0.57100(5) 0.45944(12) 0.01890(17) Uani 1 1 d . . . . .
C24 C 0.14740(7) 0.59761(5) 0.52387(13) 0.02113(18) Uani 1 1 d . . . . .
H24 H 0.1182 0.6397 0.4854 0.025 Uiso 1 1 calc R U . . .
C25 C 0.12210(7) 0.56564(5) 0.64443(12) 0.01931(17) Uani 1 1 d . . . . .
C26 C 0.16753(7) 0.50675(5) 0.70898(12) 0.01906(17) Uani 1 1 d . . . . .
H26 H 0.1541 0.4864 0.7930 0.023 Uiso 1 1 calc R U . . .
C27 C 0.23455(6) 0.47685(5) 0.64873(11) 0.01718(16) Uani 1 1 d . . . . .
O28 O 0.28039(5) 0.42169(4) 0.69969(9) 0.01976(14) Uani 1 1 d . . . . .
C29 C 0.23626(7) 0.60504(5) 0.32760(13) 0.02278(19) Uani 1 1 d . . . . .
C30 C 0.34002(8) 0.62105(6) 0.37277(15) 0.0266(2) Uani 1 1 d . . . . .
H30A H 0.3560 0.6504 0.4621 0.040 Uiso 1 1 calc R U . . .
H30B H 0.3551 0.6449 0.2902 0.040 Uiso 1 1 calc R U . . .
H30C H 0.3749 0.5780 0.3948 0.040 Uiso 1 1 calc R U . . .
C31 C 0.21109(8) 0.55609(6) 0.19144(14) 0.0276(2) Uani 1 1 d . . . . .
H31A H 0.2447 0.5127 0.2183 0.041 Uiso 1 1 calc R U . . .
H31B H 0.2277 0.5775 0.1076 0.041 Uiso 1 1 calc R U . . .
H31C H 0.1449 0.5469 0.1620 0.041 Uiso 1 1 calc R U . . .
C32 C 0.18418(10) 0.67293(6) 0.28065(17) 0.0348(3) Uani 1 1 d . . . . .
H32A H 0.1179 0.6640 0.2499 0.052 Uiso 1 1 calc R U . . .
H32B H 0.2019 0.6931 0.1966 0.052 Uiso 1 1 calc R U . . .
H32C H 0.1995 0.7050 0.3655 0.052 Uiso 1 1 calc R U . . .
C33 C 0.04498(7) 0.59796(5) 0.69796(13) 0.02263(19) Uani 1 1 d . . . . .
C34 C 0.08135(8) 0.66320(6) 0.78800(15) 0.0293(2) Uani 1 1 d . . . . .
H34A H 0.0323 0.6841 0.8226 0.044 Uiso 1 1 calc R U . . .
H34B H 0.1018 0.6960 0.7242 0.044 Uiso 1 1 calc R U . . .
H34C H 0.1332 0.6513 0.8748 0.044 Uiso 1 1 calc R U . . .
C35 C -0.03643(8) 0.61726(9) 0.56182(17) 0.0433(4) Uani 1 1 d . . . . .
H35A H -0.0530 0.5776 0.4943 0.065 Uiso 1 1 calc R U . . .
H35B H -0.0189 0.6559 0.5083 0.065 Uiso 1 1 calc R U . . .
H35C H -0.0892 0.6305 0.5963 0.065 Uiso 1 1 calc R U . . .
C36 C 0.00973(11) 0.54849(7) 0.7970(2) 0.0459(4) Uani 1 1 d . . . . .
H36A H 0.0597 0.5377 0.8874 0.069 Uiso 1 1 calc R U . . .
H36B H -0.0120 0.5060 0.7413 0.069 Uiso 1 1 calc R U . . .
H36C H -0.0410 0.5701 0.8256 0.069 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O40 1.6234(8) . ?
V1 O21 1.9172(7) . ?
V1 O1 1.9291(8) . ?
V1 N18 2.1036(9) . ?
V1 N9 2.1065(8) . ?
V1 O28 2.1300(8) . ?
O1 C2 1.3099(11) . ?
C2 C3 1.4191(14) . ?
C2 C7 1.4225(13) . ?
C3 C4 1.3798(14) . ?
C4 C5 1.4083(16) . ?
C5 C6 1.3754(15) . ?
C6 C7 1.4217(13) . ?
C7 C8 1.4314(14) . ?
C8 N9 1.3102(12) . ?
N9 C10 1.4279(13) . ?
C10 C11 1.3854(14) . ?
C10 C19 1.4237(13) . ?
C11 C12 1.4171(16) . ?
C12 C13 1.3754(16) . ?
C13 C14 1.4188(15) . ?
C14 C19 1.4167(14) . ?
C14 C15 1.4245(14) . ?
C15 C16 1.3711(15) . ?
C16 C17 1.4100(15) . ?
C17 N18 1.3275(12) . ?
N18 C19 1.3722(12) . ?
O21 C22 1.3183(11) . ?
C22 C23 1.4284(13) . ?
C22 C27 1.4350(14) . ?
C23 C24 1.3883(14) . ?
C23 C29 1.5304(15) . ?
C24 C25 1.4291(15) . ?
C25 C26 1.3811(14) . ?
C25 C33 1.5337(14) . ?
C26 C27 1.4205(13) . ?
C27 O28 1.2916(12) . ?
C29 C32 1.5355(15) . ?
C29 C30 1.5418(16) . ?
C29 C31 1.5423(17) . ?
C33 C36 1.5313(19) . ?
C33 C34 1.5322(15) . ?
C33 C35 1.5408(18) . ?

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
O40 V1 O21 94.98(3) . . ?
O40 V1 O1 99.82(4) . . ?
O21 V1 O1 96.30(3) . . ?
O40 V1 N18 93.19(4) . . ?
O21 V1 N18 94.49(3) . . ?
O1 V1 N18 162.27(3) . . ?
O40 V1 N9 103.69(3) . . ?
O21 V1 N9 160.00(3) . . ?
O1 V1 N9 87.60(3) . . ?
N18 V1 N9 77.59(3) . . ?
O40 V1 O28 170.56(3) . . ?
O21 V1 O28 77.35(3) . . ?
O1 V1 O28 86.63(3) . . ?
N18 V1 O28 82.06(3) . . ?
N9 V1 O28 83.33(3) . . ?
C2 O1 V1 133.85(7) . . ?
O1 C2 C3 118.98(9) . . ?
O1 C2 C7 122.73(9) . . ?
C3 C2 C7 118.28(9) . . ?
C4 C3 C2 120.77(10) . . ?
C3 C4 C5 121.11(10) . . ?
C6 C5 C4 119.16(10) . . ?
C5 C6 C7 121.29(10) . . ?
C6 C7 C2 119.32(9) . . ?
C6 C7 C8 117.43(9) . . ?
C2 C7 C8 123.21(8) . . ?
N9 C8 C7 126.42(9) . . ?
C8 N9 C10 119.56(8) . . ?
C8 N9 V1 125.46(7) . . ?
C10 N9 V1 114.91(6) . . ?
C11 C10 C19 118.58(9) . . ?
C11 C10 N9 126.89(9) . . ?
C19 C10 N9 114.53(8) . . ?
C10 C11 C12 120.00(10) . . ?
C13 C12 C11 121.98(10) . . ?
C12 C13 C14 119.41(10) . . ?
C19 C14 C13 118.71(9) . . ?
C19 C14 C15 117.56(9) . . ?
C13 C14 C15 123.72(10) . . ?
C16 C15 C14 119.36(9) . . ?
C15 C16 C17 119.65(9) . . ?
N18 C17 C16 122.40(10) . . ?
C17 N18 C19 119.21(9) . . ?
C17 N18 V1 124.75(7) . . ?
C19 N18 V1 115.91(6) . . ?
N18 C19 C14 121.81(9) . . ?
N18 C19 C10 116.87(9) . . ?
C14 C19 C10 121.32(9) . . ?
C22 O21 V1 119.97(6) . . ?
O21 C22 C23 124.63(9) . . ?
O21 C22 C27 114.21(8) . . ?
C23 C22 C27 121.16(9) . . ?
C24 C23 C22 115.92(9) . . ?
C24 C23 C29 123.33(9) . . ?
C22 C23 C29 120.74(9) . . ?
C23 C24 C25 124.11(9) . . ?
C26 C25 C24 119.21(9) . . ?
C26 C25 C33 122.04(10) . . ?
C24 C25 C33 118.74(9) . . ?
C25 C26 C27 119.48(9) . . ?
O28 C27 C26 124.49(9) . . ?
O28 C27 C22 115.61(8) . . ?
C26 C27 C22 119.91(9) . . ?
C27 O28 V1 112.71(6) . . ?
C23 C29 C32 112.07(9) . . ?
C23 C29 C30 109.43(9) . . ?
C32 C29 C30 107.87(9) . . ?
C23 C29 C31 109.45(9) . . ?
C32 C29 C31 108.07(10) . . ?
C30 C29 C31 109.90(9) . . ?
C36 C33 C34 108.87(11) . . ?
C36 C33 C25 111.78(9) . . ?
C34 C33 C25 109.12(9) . . ?
C36 C33 C35 108.10(12) . . ?
C34 C33 C35 109.05(10) . . ?
C25 C33 C35 109.86(10) . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_7726
_database_code_depnum_ccdc_archive 'CCDC 1506825'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2017-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_audit_creation_date             2012-03-02
_audit_block_code                WGT-PG-504-66
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N2 O4 V'
_chemical_formula_sum            'C21 H18 N2 O4 V'
_chemical_formula_weight         413.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   15.213(3)
_cell_length_b                   9.5292(12)
_cell_length_c                   12.588(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.66(2)
_cell_angle_gamma                90
_cell_volume                     1799.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    34960
_cell_measurement_theta_min      2.6978
_cell_measurement_theta_max      33.0999

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -1.00 0.0700
0.00 2.00 -1.00 0.0800
-1.00 0.00 0.00 0.0200
1.00 0.00 0.00 0.0200
1.00 2.00 -2.00 0.0800
-1.00 -2.00 2.00 0.0800
0.00 1.00 1.00 0.0800
0.00 1.00 2.00 0.0800
0.00 -1.00 -2.00 0.0700

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.583
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_absorpt_correction_T_min  0.91950
_exptl_absorpt_correction_T_max  0.97639

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_detector_area_resol_mean 18.02
_diffrn_reflns_number            31861
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.716
_diffrn_reflns_theta_max         33.072
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6823
_reflns_number_gt                4923
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_cell_refinement       'DENZO (Bruker AXS, 2006)'
_computing_data_reduction        'DENZO (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP, Version 5.03, Siemens 1994)'
_computing_publication_material  'XCIF, Version 6.12, Bruker Nonius 2001'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0264P)²+1.9156P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6823
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.27959(2) 0.10097(3) 0.38880(2) 0.01070(7) Uani 1 1 d . . . . .
O30 O 0.34778(8) 0.23203(13) 0.40486(10) 0.0152(2) Uani 1 1 d . . . . .
O1 O 0.16556(8) 0.18978(14) 0.39783(10) 0.0153(2) Uani 1 1 d . . . . .
C2 C 0.11772(11) 0.27213(18) 0.32604(14) 0.0141(3) Uani 1 1 d . . . . .
C3 C 0.04563(12) 0.3465(2) 0.35619(16) 0.0190(4) Uani 1 1 d . . . . .
H3 H 0.0320 0.3342 0.4265 0.023 Uiso 1 1 calc R U . . .
C4 C -0.00549(13) 0.4367(2) 0.28576(17) 0.0223(4) Uani 1 1 d . . . . .
H4 H -0.0537 0.4851 0.3084 0.027 Uiso 1 1 calc R U . . .
C5 C 0.01234(13) 0.4583(2) 0.18153(16) 0.0218(4) Uani 1 1 d . . . . .
H5 H -0.0220 0.5232 0.1344 0.026 Uiso 1 1 calc R U . . .
C6 C 0.08025(12) 0.38431(19) 0.14836(15) 0.0185(3) Uani 1 1 d . . . . .
H6 H 0.0919 0.3973 0.0772 0.022 Uiso 1 1 calc R U . . .
C7 C 0.13337(11) 0.28882(18) 0.21812(14) 0.0140(3) Uani 1 1 d . . . . .
C8 C 0.19707(11) 0.20977(18) 0.17165(13) 0.0136(3) Uani 1 1 d . . . . .
H8 H 0.1995 0.2256 0.0977 0.016 Uiso 1 1 calc R U . . .
N9 N 0.25191(9) 0.11796(15) 0.22209(11) 0.0119(3) Uani 1 1 d . . . . .
C10 C 0.31091(11) 0.04188(18) 0.16683(13) 0.0120(3) Uani 1 1 d . . . . .
C11 C 0.30830(12) 0.03895(19) 0.05709(13) 0.0151(3) Uani 1 1 d . . . . .
H11 H 0.2623 0.0874 0.0111 0.018 Uiso 1 1 calc R U . . .
C12 C 0.37350(13) -0.0355(2) 0.01252(14) 0.0175(3) Uani 1 1 d . . . . .
H12 H 0.3711 -0.0362 -0.0634 0.021 Uiso 1 1 calc R U . . .
C13 C 0.44003(12) -0.1067(2) 0.07675(13) 0.0169(3) Uani 1 1 d . . . . .
H13 H 0.4843 -0.1542 0.0455 0.020 Uiso 1 1 calc R U . . .
C14 C 0.44325(11) -0.10998(18) 0.18909(13) 0.0135(3) Uani 1 1 d . . . . .
C15 C 0.50986(12) -0.18233(19) 0.26037(15) 0.0165(3) Uani 1 1 d . . . . .
H15 H 0.5555 -0.2319 0.2331 0.020 Uiso 1 1 calc R U . . .
C16 C 0.50838(12) -0.18073(19) 0.36834(14) 0.0166(3) Uani 1 1 d . . . . .
H16 H 0.5523 -0.2299 0.4169 0.020 Uiso 1 1 calc R U . . .
C17 C 0.44061(11) -0.10493(19) 0.40665(13) 0.0150(3) Uani 1 1 d . . . . .
H17 H 0.4395 -0.1053 0.4819 0.018 Uiso 1 1 calc R U . . .
N18 N 0.37858(9) -0.03337(15) 0.34294(11) 0.0122(3) Uani 1 1 d . . . . .
C19 C 0.37820(11) -0.03532(17) 0.23413(13) 0.0115(3) Uani 1 1 d . . . . .
O21 O 0.20857(8) -0.09368(14) 0.36223(10) 0.0165(2) Uani 1 1 d . . . . .
C22 C 0.19183(12) -0.18374(19) 0.42943(15) 0.0173(3) Uani 1 1 d . . . . .
C23 C 0.22110(13) -0.1742(2) 0.54167(15) 0.0208(4) Uani 1 1 d . . . . .
H23 H 0.2041 -0.2466 0.5860 0.025 Uiso 1 1 calc R U . . .
C24 C 0.27304(12) -0.06595(19) 0.59103(14) 0.0166(3) Uani 1 1 d . . . . .
O25 O 0.29800(8) 0.04187(14) 0.54251(9) 0.0157(2) Uani 1 1 d . . . . .
C26 C 0.13816(14) -0.3102(2) 0.38699(17) 0.0238(4) Uani 1 1 d . . . . .
H26A H 0.1174 -0.2992 0.3094 0.036 Uiso 1 1 calc R U . . .
H26B H 0.0867 -0.3195 0.4240 0.036 Uiso 1 1 calc R U . . .
H26C H 0.1754 -0.3944 0.3999 0.036 Uiso 1 1 calc R U . . .
C27 C 0.30563(14) -0.0708(2) 0.71025(15) 0.0225(4) Uani 1 1 d . . . . .
H27A H 0.3710 -0.0719 0.7241 0.034 Uiso 1 1 calc R U . . .
H27B H 0.2831 -0.1558 0.7403 0.034 Uiso 1 1 calc R U . . .
H27C H 0.2842 0.0121 0.7442 0.034 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O30 1.6144(13) . ?
V1 O1 1.9506(13) . ?
V1 O25 1.9894(12) . ?
V1 N9 2.0763(14) . ?
V1 N18 2.1287(15) . ?
V1 O21 2.1444(13) . ?
O1 C2 1.320(2) . ?
C2 C3 1.410(2) . ?
C2 C7 1.427(2) . ?
C3 C4 1.378(3) . ?
C4 C5 1.399(3) . ?
C5 C6 1.373(3) . ?
C6 C7 1.419(2) . ?
C7 C8 1.428(2) . ?
C8 N9 1.299(2) . ?
N9 C10 1.423(2) . ?
C10 C11 1.376(2) . ?
C10 C19 1.420(2) . ?
C11 C12 1.410(3) . ?
C12 C13 1.365(3) . ?
C13 C14 1.407(2) . ?
C14 C19 1.413(2) . ?
C14 C15 1.415(2) . ?
C15 C16 1.363(3) . ?
C16 C17 1.409(2) . ?
C17 N18 1.321(2) . ?
N18 C19 1.369(2) . ?
O21 C22 1.261(2) . ?
C22 C23 1.411(3) . ?
C22 C26 1.503(3) . ?
C23 C24 1.382(3) . ?
C24 O25 1.285(2) . ?
C24 C27 1.500(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
O30 V1 O1 102.48(6) . . ?
O30 V1 O25 96.58(6) . . ?
O1 V1 O25 92.73(6) . . ?
O30 V1 N9 94.78(6) . . ?
O1 V1 N9 89.63(6) . . ?
O25 V1 N9 167.61(6) . . ?
O30 V1 N18 91.74(6) . . ?
O1 V1 N18 162.41(6) . . ?
O25 V1 N18 95.91(6) . . ?
N9 V1 N18 78.79(6) . . ?
O30 V1 O21 170.07(6) . . ?
O1 V1 O21 87.40(5) . . ?
O25 V1 O21 83.79(5) . . ?
N9 V1 O21 84.17(5) . . ?
N18 V1 O21 78.37(5) . . ?
C2 O1 V1 127.72(11) . . ?
O1 C2 C3 118.62(16) . . ?
O1 C2 C7 123.87(15) . . ?
C3 C2 C7 117.50(16) . . ?
C4 C3 C2 121.39(18) . . ?
C3 C4 C5 121.21(18) . . ?
C6 C5 C4 118.94(18) . . ?
C5 C6 C7 121.38(18) . . ?
C6 C7 C2 119.47(16) . . ?
C6 C7 C8 116.10(16) . . ?
C2 C7 C8 124.36(16) . . ?
N9 C8 C7 125.42(16) . . ?
C8 N9 C10 120.69(14) . . ?
C8 N9 V1 123.46(12) . . ?
C10 N9 V1 114.63(11) . . ?
C11 C10 C19 119.02(15) . . ?
C11 C10 N9 125.95(16) . . ?
C19 C10 N9 115.03(14) . . ?
C10 C11 C12 120.40(16) . . ?
C13 C12 C11 121.03(16) . . ?
C12 C13 C14 120.23(16) . . ?
C13 C14 C19 118.93(16) . . ?
C13 C14 C15 123.26(16) . . ?
C19 C14 C15 117.80(15) . . ?
C16 C15 C14 119.79(16) . . ?
C15 C16 C17 118.85(16) . . ?
N18 C17 C16 123.11(15) . . ?
C17 N18 C19 118.89(15) . . ?
C17 N18 V1 127.71(11) . . ?
C19 N18 V1 113.27(11) . . ?
N18 C19 C14 121.52(15) . . ?
N18 C19 C10 118.13(15) . . ?
C14 C19 C10 120.33(15) . . ?
C22 O21 V1 129.60(12) . . ?
O21 C22 C23 124.24(17) . . ?
O21 C22 C26 117.79(17) . . ?
C23 C22 C26 117.96(17) . . ?
C24 C23 C22 123.96(17) . . ?
O25 C24 C23 125.14(17) . . ?
O25 C24 C27 115.20(17) . . ?
C23 C24 C27 119.65(17) . . ?
C24 O25 V1 133.16(12) . . ?

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.089

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1506826'
_audit_update_record             
;
2016-09-27 deposited with the CCDC.
2017-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32.50 H23 Cl N4 O8 S V2'
_chemical_formula_weight         766.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   29.889(2)
_cell_length_b                   14.1920(8)
_cell_length_c                   20.2188(13)
_cell_angle_alpha                90
_cell_angle_beta                 129.985(4)
_cell_angle_gamma                90
_cell_volume                     6571.4(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.30

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_F_000             3112
_exptl_transmission_factor_min   0.420
_exptl_transmission_factor_max   0.742
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.771
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Mo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51619
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.466
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8166
_reflns_number_gt                6169
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0964P)²+19.6029P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8166
_refine_ls_number_parameters     438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1851
_refine_ls_wR_factor_gt          0.1603
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.34913(2) 0.45398(4) 0.19671(3) 0.02933(14) Uani 1 1 d . . . . .
V2 V 0.31998(2) 0.54310(4) 0.32385(3) 0.03378(15) Uani 1 1 d . . . . .
O1 O 0.39770(10) 0.40929(18) 0.19615(15) 0.0419(5) Uani 1 1 d . . . . .
O2 O 0.27688(12) 0.6094(2) 0.32299(18) 0.0552(7) Uani 1 1 d . . . . .
N1 N 0.28067(11) 0.4763(2) 0.06405(17) 0.0359(6) Uani 1 1 d . . . . .
C2 C 0.27187(16) 0.5521(3) 0.0196(2) 0.0455(8) Uani 1 1 d . . . . .
H2 H 0.2991 0.6007 0.0475 0.055 Uiso 1 1 calc R U . . .
C3 C 0.22282(18) 0.5628(3) -0.0685(3) 0.0579(11) Uani 1 1 d . . . . .
H3 H 0.2173 0.6180 -0.0977 0.070 Uiso 1 1 calc R U . . .
C4 C 0.18364(17) 0.4904(4) -0.1103(2) 0.0552(10) Uani 1 1 d . . . . .
H4 H 0.1519 0.4954 -0.1690 0.066 Uiso 1 1 calc R U . . .
C5 C 0.19108(14) 0.4086(3) -0.0650(2) 0.0432(8) Uani 1 1 d . . . . .
C6 C 0.15051(15) 0.3337(3) -0.1007(2) 0.0519(9) Uani 1 1 d . . . . .
H6 H 0.1180 0.3343 -0.1592 0.062 Uiso 1 1 calc R U . . .
C7 C 0.15858(15) 0.2608(3) -0.0504(2) 0.0497(9) Uani 1 1 d . . . . .
H7 H 0.1314 0.2120 -0.0753 0.060 Uiso 1 1 calc R U . . .
C8 C 0.20671(14) 0.2573(3) 0.0376(2) 0.0411(7) Uani 1 1 d . . . . .
H8 H 0.2107 0.2077 0.0712 0.049 Uiso 1 1 calc R U . . .
C9 C 0.24828(12) 0.3277(2) 0.07483(18) 0.0331(6) Uani 1 1 d . . . . .
C10 C 0.24076(13) 0.4044(2) 0.02358(18) 0.0350(6) Uani 1 1 d . . . . .
N11 N 0.29955(10) 0.33337(18) 0.16303(15) 0.0300(5) Uani 1 1 d . . . . .
C12 C 0.31622(13) 0.2638(2) 0.21552(19) 0.0342(6) Uani 1 1 d . . . . .
H12 H 0.2937 0.2092 0.1936 0.041 Uiso 1 1 calc R U . . .
C13 C 0.36718(13) 0.2650(2) 0.30554(19) 0.0339(6) Uani 1 1 d . . . . .
C14 C 0.38584(16) 0.1774(3) 0.3492(2) 0.0449(8) Uani 1 1 d . . . . .
H14 H 0.3646 0.1232 0.3196 0.054 Uiso 1 1 calc R U . . .
C15 C 0.43518(17) 0.1714(3) 0.4353(3) 0.0522(9) Uani 1 1 d . . . . .
H15 H 0.4476 0.1133 0.4630 0.063 Uiso 1 1 calc R U . . .
C16 C 0.46578(15) 0.2523(3) 0.4798(2) 0.0464(8) Uani 1 1 d . . . . .
H16 H 0.4990 0.2483 0.5376 0.056 Uiso 1 1 calc R U . . .
C17 C 0.44768(13) 0.3388(3) 0.43946(19) 0.0376(7) Uani 1 1 d . . . . .
H17 H 0.4687 0.3924 0.4710 0.045 Uiso 1 1 calc R U . . .
C18 C 0.39846(12) 0.3481(2) 0.35210(18) 0.0313(6) Uani 1 1 d . . . . .
O19 O 0.38164(9) 0.43378(15) 0.31681(12) 0.0327(4) Uani 1 1 d . . . . .
N21 N 0.38335(11) 0.5174(2) 0.45695(16) 0.0367(6) Uani 1 1 d . . . . .
C22 C 0.42823(15) 0.5723(3) 0.5140(2) 0.0473(8) Uani 1 1 d . . . . .
H22 H 0.4317 0.6300 0.4958 0.057 Uiso 1 1 calc R U . . .
C23 C 0.47074(17) 0.5467(3) 0.6007(2) 0.0559(10) Uani 1 1 d . . . . .
H23 H 0.5019 0.5868 0.6389 0.067 Uiso 1 1 calc R U . . .
C24 C 0.46632(16) 0.4631(3) 0.6288(2) 0.0540(10) Uani 1 1 d . . . . .
H24 H 0.4950 0.4451 0.6860 0.065 Uiso 1 1 calc R U . . .
C25 C 0.41813(15) 0.4034(3) 0.5710(2) 0.0450(8) Uani 1 1 d . . . . .
C26 C 0.40959(18) 0.3155(3) 0.5935(2) 0.0546(10) Uani 1 1 d . . . . .
H26 H 0.4353 0.2951 0.6505 0.066 Uiso 1 1 calc R U . . .
C27 C 0.36367(19) 0.2600(3) 0.5319(2) 0.0538(9) Uani 1 1 d . . . . .
H27 H 0.3589 0.2016 0.5477 0.065 Uiso 1 1 calc R U . . .
C28 C 0.32299(16) 0.2888(3) 0.4445(2) 0.0465(8) Uani 1 1 d . . . . .
H28 H 0.2922 0.2494 0.4036 0.056 Uiso 1 1 calc R U . . .
C29 C 0.32909(13) 0.3748(2) 0.42065(19) 0.0352(6) Uani 1 1 d . . . . .
C30 C 0.37705(14) 0.4337(3) 0.48378(19) 0.0363(7) Uani 1 1 d . . . . .
N31 N 0.29284(11) 0.4144(2) 0.33650(16) 0.0335(5) Uani 1 1 d . . . . .
C32 C 0.24322(14) 0.3760(3) 0.2734(2) 0.0393(7) Uani 1 1 d . . . . .
H32 H 0.2322 0.3210 0.2847 0.047 Uiso 1 1 calc R U . . .
C33 C 0.20436(13) 0.4137(3) 0.1873(2) 0.0390(7) Uani 1 1 d . . . . .
C34 C 0.14695(15) 0.3773(3) 0.1316(2) 0.0534(9) Uani 1 1 d . . . . .
H34 H 0.1365 0.3304 0.1516 0.064 Uiso 1 1 calc R U . . .
C35 C 0.10624(16) 0.4098(4) 0.0486(3) 0.0608(11) Uani 1 1 d . . . . .
H35 H 0.0686 0.3850 0.0126 0.073 Uiso 1 1 calc R U . . .
C36 C 0.12175(16) 0.4794(3) 0.0195(2) 0.0526(9) Uani 1 1 d . . . . .
H36 H 0.0941 0.5018 -0.0365 0.063 Uiso 1 1 calc R U . . .
C37 C 0.17702(14) 0.5166(3) 0.0711(2) 0.0419(7) Uani 1 1 d . . . . .
H37 H 0.1861 0.5644 0.0501 0.050 Uiso 1 1 calc R U . . .
C38 C 0.21984(13) 0.4830(2) 0.15530(19) 0.0345(6) Uani 1 1 d . . . . .
O39 O 0.27499(9) 0.51488(16) 0.20132(13) 0.0347(5) Uani 1 1 d . . . . .
S40 S 0.37381(4) 0.67037(5) 0.25958(5) 0.0385(2) Uani 1 1 d . . . . .
O41 O 0.37160(11) 0.58722(17) 0.21255(16) 0.0446(6) Uani 1 1 d . . . . .
O42 O 0.37240(11) 0.63329(17) 0.32777(15) 0.0432(5) Uani 1 1 d . . . . .
O43 O 0.32302(15) 0.7283(2) 0.1993(2) 0.0720(9) Uani 1 1 d . . . . .
O44 O 0.42816(14) 0.7181(2) 0.3018(2) 0.0702(9) Uani 1 1 d . . . . .
C60 C 0.0000 0.2397(6) -0.2500 0.0676(18) Uani 1 2 d S T P . .
H60A H 0.0341 0.1991 -0.2166 0.081 Uiso 0.5 1 calc R U P . .
H60B H -0.0341 0.1991 -0.2834 0.081 Uiso 0.5 1 calc R U P . .
Cl61 Cl 0.00168(8) 0.30015(15) -0.31945(12) 0.1117(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O1 1.591(2) . ?
V1 O41 1.963(2) . ?
V1 O19 1.972(2) . ?
V1 N11 2.072(2) . ?
V1 N1 2.104(3) . ?
V1 O39 2.436(2) . ?
V2 O2 1.586(3) . ?
V2 O39 1.956(2) . ?
V2 O42 1.985(2) . ?
V2 N31 2.080(3) . ?
V2 N21 2.100(3) . ?
N1 C2 1.316(4) . ?
N1 C10 1.370(4) . ?
C2 C3 1.411(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.406(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(6) . ?
C5 C10 1.413(4) . ?
C6 C7 1.360(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.418(5) . ?
C9 N11 1.422(4) . ?
N11 C12 1.292(4) . ?
C12 C13 1.439(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.416(5) . ?
C13 C18 1.421(4) . ?
C14 C15 1.383(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.401(4) . ?
C17 H17 0.9300 . ?
C18 O19 1.334(4) . ?
N21 C22 1.322(4) . ?
N21 C30 1.368(4) . ?
C22 C23 1.398(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.358(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.412(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.407(6) . ?
C25 C30 1.421(4) . ?
C26 C27 1.363(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.416(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.368(5) . ?
C28 H28 0.9300 . ?
C29 N31 1.419(4) . ?
C29 C30 1.425(4) . ?
N31 C32 1.301(4) . ?
C32 C33 1.438(5) . ?
C32 H32 0.9300 . ?
C33 C38 1.409(5) . ?
C33 C34 1.413(5) . ?
C34 C35 1.373(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.375(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.372(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.401(4) . ?
C37 H37 0.9300 . ?
C38 O39 1.348(4) . ?
S40 O44 1.430(3) . ?
S40 O43 1.445(3) . ?
S40 O41 1.490(2) . ?
S40 O42 1.501(3) . ?
C60 Cl61 1.674(4) . ?
C60 Cl61 1.674(4) 2_554 ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O41 99.63(12) . . ?
O1 V1 O19 102.76(11) . . ?
O41 V1 O19 95.33(10) . . ?
O1 V1 N11 97.55(11) . . ?
O41 V1 N11 161.26(11) . . ?
O19 V1 N11 88.11(9) . . ?
O1 V1 N1 101.25(12) . . ?
O41 V1 N1 90.79(11) . . ?
O19 V1 N1 153.82(10) . . ?
N11 V1 N1 78.52(10) . . ?
O1 V1 O39 176.97(11) . . ?
O41 V1 O39 82.89(9) . . ?
O19 V1 O39 75.23(8) . . ?
N11 V1 O39 80.19(9) . . ?
N1 V1 O39 80.33(9) . . ?
O2 V2 O39 102.42(12) . . ?
O2 V2 O42 103.46(14) . . ?
O39 V2 O42 93.74(10) . . ?
O2 V2 N31 98.27(14) . . ?
O39 V2 N31 88.33(10) . . ?
O42 V2 N31 157.16(11) . . ?
O2 V2 N21 100.03(13) . . ?
O39 V2 N21 155.15(11) . . ?
O42 V2 N21 91.26(11) . . ?
N31 V2 N21 77.99(10) . . ?
C2 N1 C10 119.1(3) . . ?
C2 N1 V1 126.7(2) . . ?
C10 N1 V1 114.2(2) . . ?
N1 C2 C3 122.6(4) . . ?
N1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 124.3(3) . . ?
C4 C5 C10 117.2(3) . . ?
C6 C5 C10 118.3(3) . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.5(3) . . ?
C8 C9 N11 126.3(3) . . ?
C10 C9 N11 114.2(3) . . ?
N1 C10 C5 121.9(3) . . ?
N1 C10 C9 117.8(3) . . ?
C5 C10 C9 120.1(3) . . ?
C12 N11 C9 121.5(3) . . ?
C12 N11 V1 122.99(19) . . ?
C9 N11 V1 115.21(19) . . ?
N11 C12 C13 124.5(3) . . ?
N11 C12 H12 117.8 . . ?
C13 C12 H12 117.8 . . ?
C14 C13 C18 119.2(3) . . ?
C14 C13 C12 116.8(3) . . ?
C18 C13 C12 124.0(3) . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 121.7(3) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
O19 C18 C17 119.3(3) . . ?
O19 C18 C13 122.7(3) . . ?
C17 C18 C13 117.9(3) . . ?
C18 O19 V1 120.60(18) . . ?
C22 N21 C30 119.1(3) . . ?
C22 N21 V2 126.1(3) . . ?
C30 N21 V2 114.7(2) . . ?
N21 C22 C23 122.4(4) . . ?
N21 C22 H22 118.8 . . ?
C23 C22 H22 118.8 . . ?
C24 C23 C22 119.8(4) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 124.4(3) . . ?
C26 C25 C30 118.6(3) . . ?
C24 C25 C30 117.0(4) . . ?
C27 C26 C25 120.2(3) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 121.7(4) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C29 C28 C27 119.7(3) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 N31 127.2(3) . . ?
C28 C29 C30 119.5(3) . . ?
N31 C29 C30 113.3(3) . . ?
N21 C30 C25 121.7(3) . . ?
N21 C30 C29 118.0(3) . . ?
C25 C30 C29 120.2(3) . . ?
C32 N31 C29 121.4(3) . . ?
C32 N31 V2 122.4(2) . . ?
C29 N31 V2 115.9(2) . . ?
N31 C32 C33 123.8(3) . . ?
N31 C32 H32 118.1 . . ?
C33 C32 H32 118.1 . . ?
C38 C33 C34 118.6(3) . . ?
C38 C33 C32 124.6(3) . . ?
C34 C33 C32 116.8(3) . . ?
C35 C34 C33 121.3(4) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
C34 C35 C36 119.2(3) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C37 C36 C35 121.6(3) . . ?
C37 C36 H36 119.2 . . ?
C35 C36 H36 119.2 . . ?
C36 C37 C38 120.4(4) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
O39 C38 C37 118.8(3) . . ?
O39 C38 C33 122.3(3) . . ?
C37 C38 C33 118.8(3) . . ?
C38 O39 V2 118.93(19) . . ?
C38 O39 V1 126.43(18) . . ?
V2 O39 V1 102.66(9) . . ?
O44 S40 O43 114.1(2) . . ?
O44 S40 O41 108.89(19) . . ?
O43 S40 O41 108.71(18) . . ?
O44 S40 O42 108.03(16) . . ?
O43 S40 O42 109.86(18) . . ?
O41 S40 O42 107.00(14) . . ?
S40 O41 V1 137.51(16) . . ?
S40 O42 V2 132.58(14) . . ?
Cl61 C60 Cl61 118.3(5) . 2_554 ?
Cl61 C60 H60A 107.7 . . ?
Cl61 C60 H60A 107.7 2_554 . ?
Cl61 C60 H60B 107.7 . . ?
Cl61 C60 H60B 107.7 2_554 . ?
H60A C60 H60B 107.1 . . ?

_refine_diff_density_max         1.320
_refine_diff_density_min         -1.254
_refine_diff_density_rms         0.100

_shelxl_version_number           2013-2



