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

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

data_g-15
_database_code_depnum_ccdc_archive 'CCDC 1407700'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N7 O S2 V'
_chemical_formula_sum            'C14 H19 N7 O S2 V'
_chemical_formula_weight         416.42

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'
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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.8544(4)
_cell_length_b                   11.2802(4)
_cell_length_c                   19.5722(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.708(4)
_cell_angle_gamma                90
_cell_volume                     1920.82(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2913
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      25.24

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.751
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   'CrysAlis 1.171.33.42'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'KUMA KM-4 with area CCD detector'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2, 33.133pixel/mm'
_diffrn_reflns_number            22463
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.743
_diffrn_reflns_theta_max         26.372
_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             3912
_reflns_number_gt                2913
_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       'CrysAlis 1.171.32.6'
_computing_cell_refinement       'CrysAlis 1.171.32.6'
_computing_data_reduction        'CrysAlis 1.171.33.42'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0225P)²+2.4911P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3912
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001

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 0.36665(6) 0.23265(5) 0.28442(3) 0.03093(15) Uani 1 1 d . . . . .
O1 O 0.3633(3) 0.37206(19) 0.29673(12) 0.0454(6) Uani 1 1 d . . . . .
N1 N 0.4024(3) 0.0263(2) 0.28312(13) 0.0319(6) Uani 1 1 d . . . . .
H1 H 0.3275 -0.0065 0.2446 0.038 Uiso 1 1 calc R U . . .
S2 S -0.14752(12) 0.19320(9) 0.16408(6) 0.0593(3) Uani 1 1 d . . . . .
C2 C 0.0222(4) 0.1967(3) 0.21109(17) 0.0379(8) Uani 1 1 d . . . . .
N2 N 0.1426(3) 0.2001(3) 0.24637(15) 0.0461(7) Uani 1 1 d . . . . .
N11 N 0.6587(3) 0.0913(2) 0.30902(14) 0.0345(6) Uani 1 1 d . . . . .
S4 S 0.46780(14) 0.14415(11) 0.06036(5) 0.0673(3) Uani 1 1 d . . . . .
N3 N 0.4036(3) 0.2227(3) 0.18608(14) 0.0414(7) Uani 1 1 d . . . . .
C3 C 0.4290(4) 0.1900(3) 0.13312(18) 0.0398(8) Uani 1 1 d . . . . .
N12 N 0.6028(3) 0.2013(2) 0.32016(13) 0.0333(6) Uani 1 1 d . . . . .
C13 C 0.7219(4) 0.2618(3) 0.35546(16) 0.0378(8) Uani 1 1 d . . . . .
C14 C 0.8528(4) 0.1910(3) 0.36455(18) 0.0453(9) Uani 1 1 d . . . . .
H14 H 0.9510 0.2126 0.3868 0.054 Uiso 1 1 calc R U . . .
C15 C 0.8105(4) 0.0843(3) 0.33480(18) 0.0403(8) Uani 1 1 d . . . . .
C16 C 0.7057(5) 0.3844(3) 0.3811(2) 0.0558(10) Uani 1 1 d . . . . .
H16A H 0.6704 0.3813 0.4245 0.084 Uiso 1 1 calc R U . . .
H16B H 0.6328 0.4272 0.3476 0.084 Uiso 1 1 calc R U . . .
H16C H 0.8035 0.4237 0.3876 0.084 Uiso 1 1 calc R U . . .
C17 C 0.9026(4) -0.0247(4) 0.3282(2) 0.0619(11) Uani 1 1 d . . . . .
H17A H 1.0036 -0.0159 0.3558 0.093 Uiso 1 1 calc R U . . .
H17B H 0.9104 -0.0360 0.2804 0.093 Uiso 1 1 calc R U . . .
H17C H 0.8529 -0.0921 0.3443 0.093 Uiso 1 1 calc R U . . .
C18 C 0.5566(4) 0.0074(3) 0.26772(17) 0.0373(8) Uani 1 1 d . . . . .
H18A H 0.5905 -0.0731 0.2795 0.045 Uiso 1 1 calc R U . . .
H18B H 0.5558 0.0200 0.2186 0.045 Uiso 1 1 calc R U . . .
N21 N 0.3349(3) 0.0548(2) 0.39528(13) 0.0341(6) Uani 1 1 d . . . . .
N22 N 0.3318(3) 0.1733(2) 0.38215(13) 0.0340(6) Uani 1 1 d . . . . .
C23 C 0.2925(4) 0.2245(3) 0.43793(18) 0.0446(9) Uani 1 1 d . . . . .
C24 C 0.2707(5) 0.1386(4) 0.48512(19) 0.0554(10) Uani 1 1 d . . . . .
H24 H 0.2419 0.1514 0.5279 0.067 Uiso 1 1 calc R U . . .
C25 C 0.2988(4) 0.0315(3) 0.45789(17) 0.0464(9) Uani 1 1 d . . . . .
C26 C 0.2771(6) 0.3560(4) 0.4443(2) 0.0740(14) Uani 1 1 d . . . . .
H26A H 0.1856 0.3823 0.4137 0.111 Uiso 1 1 calc R U . . .
H26B H 0.3650 0.3943 0.4319 0.111 Uiso 1 1 calc R U . . .
H26C H 0.2706 0.3758 0.4914 0.111 Uiso 1 1 calc R U . . .
C28 C 0.3785(4) -0.0308(3) 0.34714(18) 0.0462(9) Uani 1 1 d . . . . .
H28A H 0.2985 -0.0903 0.3362 0.055 Uiso 1 1 calc R U . . .
H28B H 0.4724 -0.0705 0.3689 0.055 Uiso 1 1 calc R U . . .
C27 C 0.2959(6) -0.0921(4) 0.4850(2) 0.0697(13) Uani 1 1 d . . . . .
H27A H 0.3767 -0.1375 0.4710 0.105 Uiso 1 1 calc R U . . .
H27B H 0.1985 -0.1279 0.4666 0.105 Uiso 1 1 calc R U . . .
H27C H 0.3107 -0.0904 0.5348 0.105 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 O1 1.592(2) . ?
V1 N3 2.015(3) . ?
V1 N2 2.019(3) . ?
V1 N22 2.103(3) . ?
V1 N12 2.108(3) . ?
V1 N1 2.350(3) . ?
N1 C28 1.459(4) . ?
N1 C18 1.468(4) . ?
N1 H1 0.9800 . ?
S2 C2 1.610(4) . ?
C2 N2 1.158(4) . ?
N11 C15 1.347(4) . ?
N11 N12 1.368(3) . ?
N11 C18 1.448(4) . ?
S4 C3 1.611(4) . ?
N3 C3 1.161(4) . ?
N12 C13 1.336(4) . ?
C13 C14 1.392(5) . ?
C13 C16 1.486(5) . ?
C14 C15 1.359(5) . ?
C14 H14 0.9300 . ?
C15 C17 1.493(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N21 C25 1.348(4) . ?
N21 N22 1.360(3) . ?
N21 C28 1.451(4) . ?
N22 C23 1.337(4) . ?
C23 C24 1.377(5) . ?
C23 C26 1.497(5) . ?
C24 C25 1.362(5) . ?
C24 H24 0.9300 . ?
C25 C27 1.494(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 N3 102.14(12) . . ?
O1 V1 N2 100.98(12) . . ?
N3 V1 N2 87.73(12) . . ?
O1 V1 N22 99.60(11) . . ?
N3 V1 N22 158.25(11) . . ?
N2 V1 N22 88.72(11) . . ?
O1 V1 N12 99.25(11) . . ?
N3 V1 N12 88.88(11) . . ?
N2 V1 N12 159.75(11) . . ?
N22 V1 N12 87.07(10) . . ?
O1 V1 N1 170.56(11) . . ?
N3 V1 N1 83.60(10) . . ?
N2 V1 N1 86.62(11) . . ?
N22 V1 N1 74.77(9) . . ?
N12 V1 N1 73.16(9) . . ?
C28 N1 C18 113.6(3) . . ?
C28 N1 V1 112.76(19) . . ?
C18 N1 V1 106.16(18) . . ?
C28 N1 H1 108.0 . . ?
C18 N1 H1 108.0 . . ?
V1 N1 H1 108.0 . . ?
N2 C2 S2 178.2(3) . . ?
C2 N2 V1 163.5(3) . . ?
C15 N11 N12 111.0(3) . . ?
C15 N11 C18 130.3(3) . . ?
N12 N11 C18 118.4(2) . . ?
C3 N3 V1 164.5(3) . . ?
N3 C3 S4 178.9(3) . . ?
C13 N12 N11 105.7(3) . . ?
C13 N12 V1 136.5(2) . . ?
N11 N12 V1 117.73(19) . . ?
N12 C13 C14 109.4(3) . . ?
N12 C13 C16 122.2(3) . . ?
C14 C13 C16 128.4(3) . . ?
C15 C14 C13 107.3(3) . . ?
C15 C14 H14 126.4 . . ?
C13 C14 H14 126.4 . . ?
N11 C15 C14 106.5(3) . . ?
N11 C15 C17 122.6(3) . . ?
C14 C15 C17 130.9(3) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N11 C18 N1 107.4(2) . . ?
N11 C18 H18A 110.2 . . ?
N1 C18 H18A 110.2 . . ?
N11 C18 H18B 110.2 . . ?
N1 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
C25 N21 N22 111.3(3) . . ?
C25 N21 C28 126.6(3) . . ?
N22 N21 C28 122.0(2) . . ?
C23 N22 N21 105.6(3) . . ?
C23 N22 V1 135.2(2) . . ?
N21 N22 V1 118.91(19) . . ?
N22 C23 C24 109.5(3) . . ?
N22 C23 C26 122.5(3) . . ?
C24 C23 C26 127.9(3) . . ?
C25 C24 C23 107.6(3) . . ?
C25 C24 H24 126.2 . . ?
C23 C24 H24 126.2 . . ?
N21 C25 C24 105.9(3) . . ?
N21 C25 C27 121.8(3) . . ?
C24 C25 C27 132.3(3) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N21 C28 N1 111.2(3) . . ?
N21 C28 H28A 109.4 . . ?
N1 C28 H28A 109.4 . . ?
N21 C28 H28B 109.4 . . ?
N1 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 C13 -1.9(3) . . . . ?
C18 N11 N12 C13 -176.3(3) . . . . ?
C15 N11 N12 V1 -179.7(2) . . . . ?
C18 N11 N12 V1 5.9(3) . . . . ?
N11 N12 C13 C14 1.7(3) . . . . ?
V1 N12 C13 C14 178.9(2) . . . . ?
N11 N12 C13 C16 -176.5(3) . . . . ?
V1 N12 C13 C16 0.7(5) . . . . ?
N12 C13 C14 C15 -1.0(4) . . . . ?
C16 C13 C14 C15 177.2(3) . . . . ?
N12 N11 C15 C14 1.4(4) . . . . ?
C18 N11 C15 C14 174.8(3) . . . . ?
N12 N11 C15 C17 -178.3(3) . . . . ?
C18 N11 C15 C17 -4.8(5) . . . . ?
C13 C14 C15 N11 -0.2(4) . . . . ?
C13 C14 C15 C17 179.4(4) . . . . ?
C15 N11 C18 N1 151.5(3) . . . . ?
N12 N11 C18 N1 -35.4(4) . . . . ?
C28 N1 C18 N11 -81.1(3) . . . . ?
V1 N1 C18 N11 43.4(3) . . . . ?
C25 N21 N22 C23 -0.1(4) . . . . ?
C28 N21 N22 C23 -177.8(3) . . . . ?
C25 N21 N22 V1 -175.2(2) . . . . ?
C28 N21 N22 V1 7.1(4) . . . . ?
N21 N22 C23 C24 -0.3(4) . . . . ?
V1 N22 C23 C24 173.5(3) . . . . ?
N21 N22 C23 C26 179.7(4) . . . . ?
V1 N22 C23 C26 -6.5(6) . . . . ?
N22 C23 C24 C25 0.6(4) . . . . ?
C26 C23 C24 C25 -179.4(4) . . . . ?
N22 N21 C25 C24 0.5(4) . . . . ?
C28 N21 C25 C24 178.1(3) . . . . ?
N22 N21 C25 C27 -179.2(3) . . . . ?
C28 N21 C25 C27 -1.7(6) . . . . ?
C23 C24 C25 N21 -0.7(4) . . . . ?
C23 C24 C25 C27 179.1(4) . . . . ?
C25 N21 C28 N1 177.3(3) . . . . ?
N22 N21 C28 N1 -5.3(4) . . . . ?
C18 N1 C28 N21 122.2(3) . . . . ?
V1 N1 C28 N21 1.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.98 2.21 3.104(3) 151.5 2_545
C16 H16B O1 0.96 2.49 3.175(4) 128.3 .
C16 H16B S2 0.96 3.01 3.608(4) 121.4 2
C17 H17C S2 0.96 3.02 3.921(4) 158.0 2_545
C18 H18A S2 0.97 2.87 3.820(3) 167.5 2_545
C27 H27B S4 0.96 2.96 3.784(4) 144.6 2_545

_refine_diff_density_max         0.558
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.065



####################################################################### 
# 
# 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 
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data_g-1
_database_code_depnum_ccdc_archive 'CCDC 1407701'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N7 O S2 V, C7 H8'
_chemical_formula_sum            'C21 H27 N7 O S2 V'
_chemical_formula_weight         508.55

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'
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           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

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

_cell_length_a                   7.7159(7)
_cell_length_b                   16.2503(12)
_cell_length_c                   10.3876(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.466(9)
_cell_angle_gamma                90
_cell_volume                     1266.65(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1578
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.24

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             530
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.583
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'CrysAlis 1.171.33.42'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'KUMA KM-4 with area CCD detector'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2, 33.133pixel/mm'
_diffrn_reflns_number            11488
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.981
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2403
_reflns_number_gt                1578
_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       'CrysAlis 1.171.32.6'
_computing_cell_refinement       'CrysAlis 1.171.32.6'
_computing_data_reduction        'CrysAlis 1.171.33.42'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2403
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001

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 0.25519(8) 0.2500 0.94126(6) 0.0486(2) Uani 1 2 d S T P . .
S2 S 0.28025(13) 0.04300(5) 0.61874(9) 0.0871(3) Uani 1 1 d . . . . .
O1 O 0.4483(3) 0.2500 1.0358(3) 0.0652(7) Uani 1 2 d S T P . .
N1 N -0.0466(4) 0.2500 0.8290(3) 0.0472(7) Uani 1 2 d S T P . .
H1 H -0.0495 0.2500 0.7342 0.057 Uiso 1 2 calc R U P . .
N2 N 0.2762(3) 0.16245(14) 0.8072(2) 0.0625(6) Uani 1 1 d . . . . .
N11 N -0.0456(3) 0.14544(12) 0.98938(19) 0.0487(5) Uani 1 1 d . . . . .
N12 N 0.1312(2) 0.16210(13) 1.04033(18) 0.0482(5) Uani 1 1 d . . . . .
C2 C 0.2777(3) 0.11291(16) 0.7280(3) 0.0521(7) Uani 1 1 d . . . . .
C13 C 0.1744(3) 0.11987(15) 1.1543(2) 0.0485(6) Uani 1 1 d . . . . .
C14 C 0.0264(4) 0.07618(17) 1.1717(3) 0.0592(7) Uani 1 1 d . . . . .
H14 H 0.0215 0.0421 1.2427 0.071 Uiso 1 1 calc R U . . .
C15 C -0.1103(3) 0.09258(16) 1.0652(3) 0.0532(7) Uani 1 1 d . . . . .
C16 C 0.3541(4) 0.1243(2) 1.2442(3) 0.0716(8) Uani 1 1 d . . . . .
H16A H 0.4086 0.1760 1.2319 0.107 Uiso 0.5 1 calc R U P . .
H16B H 0.4263 0.0801 1.2246 0.107 Uiso 0.5 1 calc R U P . .
H16C H 0.3439 0.1199 1.3343 0.107 Uiso 0.5 1 calc R U P . .
H16D H 0.3772 0.0747 1.2953 0.107 Uiso 0.5 1 calc R U P . .
H16E H 0.3596 0.1706 1.3026 0.107 Uiso 0.5 1 calc R U P . .
H16F H 0.4420 0.1307 1.1929 0.107 Uiso 0.5 1 calc R U P . .
C17 C -0.2993(3) 0.0625(2) 1.0285(3) 0.0756(9) Uani 1 1 d . . . . .
H17A H -0.3473 0.0709 0.9356 0.113 Uiso 0.5 1 calc R U P . .
H17B H -0.3692 0.0923 1.0781 0.113 Uiso 0.5 1 calc R U P . .
H17C H -0.3022 0.0049 1.0484 0.113 Uiso 0.5 1 calc R U P . .
H17D H -0.3318 0.0412 1.1058 0.113 Uiso 0.5 1 calc R U P . .
H17E H -0.3099 0.0197 0.9633 0.113 Uiso 0.5 1 calc R U P . .
H17F H -0.3770 0.1072 0.9930 0.113 Uiso 0.5 1 calc R U P . .
C18 C -0.1282(4) 0.17348(18) 0.8562(3) 0.0654(8) Uani 1 1 d . . . . .
H18A H -0.1135 0.1320 0.7924 0.079 Uiso 1 1 calc R U . . .
H18B H -0.2548 0.1818 0.8480 0.079 Uiso 1 1 calc R U . . .
C21 C -0.1029(5) 0.2500 0.4747(4) 0.0590(10) Uani 1 2 d S T P . .
C22 C -0.1815(4) 0.1775(2) 0.4969(3) 0.0726(8) Uani 1 1 d . . . . .
H22 H -0.1299 0.1278 0.4818 0.087 Uiso 1 1 calc R U . . .
C23 C -0.3361(5) 0.1774(3) 0.5414(3) 0.0949(12) Uani 1 1 d . . . . .
H23 H -0.3877 0.1277 0.5565 0.114 Uiso 1 1 calc R U . . .
C24 C -0.4146(6) 0.2500 0.5635(5) 0.108(2) Uani 1 2 d S T P . .
H24 H -0.5195 0.2500 0.5930 0.129 Uiso 1 2 calc R U P . .
C25 C 0.0648(7) 0.2500 0.4245(5) 0.0926(15) Uani 1 2 d S T P . .
H25A H 0.0181 0.2500 0.3293 0.139 Uiso 1 2 d S U P . .
H25B H 0.1295 0.2015 0.4515 0.139 Uiso 1 1 d . 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 O1 1.582(3) . ?
V1 N2 2.024(2) . ?
V1 N2 2.024(2) 4_565 ?
V1 N12 2.115(2) . ?
V1 N12 2.115(2) 4_565 ?
V1 N1 2.349(3) . ?
S2 C2 1.609(3) . ?
N1 C18 1.451(3) . ?
N1 C18 1.451(3) 4_565 ?
N1 H1 0.9800 . ?
N2 C2 1.153(3) . ?
N11 C15 1.338(3) . ?
N11 N12 1.370(3) . ?
N11 C18 1.455(3) . ?
N12 C13 1.341(3) . ?
C13 C14 1.392(3) . ?
C13 C16 1.482(3) . ?
C14 C15 1.365(4) . ?
C14 H14 0.9300 . ?
C15 C17 1.501(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 H16D 0.9600 . ?
C16 H16E 0.9600 . ?
C16 H16F 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 H17D 0.9600 . ?
C17 H17E 0.9600 . ?
C17 H17F 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C21 C22 1.369(3) . ?
C21 C22 1.369(3) 4_565 ?
C21 C25 1.504(6) . ?
C22 C23 1.376(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(4) . ?
C23 H23 0.9300 . ?
C24 C23 1.370(4) 4_565 ?
C24 H24 0.9300 . ?
C25 H25A 0.9709 . ?
C25 H25B 0.9399 . ?

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 N2 102.27(9) . . ?
O1 V1 N2 102.27(9) . 4_565 ?
N2 V1 N2 89.35(12) . 4_565 ?
O1 V1 N12 99.52(9) . . ?
N2 V1 N12 88.73(8) . . ?
N2 V1 N12 158.03(9) 4_565 . ?
O1 V1 N12 99.52(9) . 4_565 ?
N2 V1 N12 158.03(9) . 4_565 ?
N2 V1 N12 88.72(8) 4_565 4_565 ?
N12 V1 N12 84.96(11) . 4_565 ?
O1 V1 N1 171.74(12) . . ?
N2 V1 N1 83.52(8) . . ?
N2 V1 N1 83.52(8) 4_565 . ?
N12 V1 N1 74.52(7) . . ?
N12 V1 N1 74.52(7) 4_565 . ?
C18 N1 C18 118.0(3) . 4_565 ?
C18 N1 V1 109.15(15) . . ?
C18 N1 V1 109.15(15) 4_565 . ?
C18 N1 H1 106.7 . . ?
C18 N1 H1 106.7 4_565 . ?
V1 N1 H1 106.7 . . ?
C2 N2 V1 176.1(2) . . ?
C15 N11 N12 111.96(19) . . ?
C15 N11 C18 128.3(2) . . ?
N12 N11 C18 118.8(2) . . ?
C13 N12 N11 105.1(2) . . ?
C13 N12 V1 136.64(18) . . ?
N11 N12 V1 117.90(14) . . ?
N2 C2 S2 179.4(3) . . ?
N12 C13 C14 109.4(2) . . ?
N12 C13 C16 122.3(2) . . ?
C14 C13 C16 128.2(2) . . ?
C15 C14 C13 107.3(2) . . ?
C15 C14 H14 126.3 . . ?
C13 C14 H14 126.3 . . ?
N11 C15 C14 106.2(2) . . ?
N11 C15 C17 122.3(2) . . ?
C14 C15 C17 131.6(3) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C16 H16D 109.5 . . ?
H16A C16 H16D 141.1 . . ?
H16B C16 H16D 56.3 . . ?
H16C C16 H16D 56.3 . . ?
C13 C16 H16E 109.5 . . ?
H16A C16 H16E 56.3 . . ?
H16B C16 H16E 141.1 . . ?
H16C C16 H16E 56.3 . . ?
H16D C16 H16E 109.5 . . ?
C13 C16 H16F 109.5 . . ?
H16A C16 H16F 56.3 . . ?
H16B C16 H16F 56.3 . . ?
H16C C16 H16F 141.1 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C17 H17D 109.5 . . ?
H17A C17 H17D 141.1 . . ?
H17B C17 H17D 56.3 . . ?
H17C C17 H17D 56.3 . . ?
C15 C17 H17E 109.5 . . ?
H17A C17 H17E 56.3 . . ?
H17B C17 H17E 141.1 . . ?
H17C C17 H17E 56.3 . . ?
H17D C17 H17E 109.5 . . ?
C15 C17 H17F 109.5 . . ?
H17A C17 H17F 56.3 . . ?
H17B C17 H17F 56.3 . . ?
H17C C17 H17F 141.1 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
N1 C18 N11 109.9(2) . . ?
N1 C18 H18A 109.7 . . ?
N11 C18 H18A 109.7 . . ?
N1 C18 H18B 109.7 . . ?
N11 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C22 C21 C22 118.8(4) . 4_565 ?
C22 C21 C25 120.6(2) . . ?
C22 C21 C25 120.6(2) 4_565 . ?
C21 C22 C23 120.7(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.5(4) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C23 118.9(5) . 4_565 ?
C23 C24 H24 120.5 . . ?
C23 C24 H24 120.5 4_565 . ?
C21 C25 H25A 102.0 . . ?
C21 C25 H25B 109.7 . . ?
H25A C25 H25B 110.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 C13 -2.2(2) . . . . ?
C18 N11 N12 C13 -171.9(2) . . . . ?
C15 N11 N12 V1 -176.38(16) . . . . ?
C18 N11 N12 V1 13.9(3) . . . . ?
N11 N12 C13 C14 1.3(3) . . . . ?
V1 N12 C13 C14 173.85(18) . . . . ?
N11 N12 C13 C16 -177.1(2) . . . . ?
V1 N12 C13 C16 -4.5(4) . . . . ?
N12 C13 C14 C15 -0.1(3) . . . . ?
C16 C13 C14 C15 178.2(2) . . . . ?
N12 N11 C15 C14 2.1(3) . . . . ?
C18 N11 C15 C14 170.7(2) . . . . ?
N12 N11 C15 C17 -178.0(2) . . . . ?
C18 N11 C15 C17 -9.5(4) . . . . ?
C13 C14 C15 N11 -1.2(3) . . . . ?
C13 C14 C15 C17 179.0(3) . . . . ?
C18 N1 C18 N11 -92.6(3) 4_565 . . . ?
V1 N1 C18 N11 32.7(3) . . . . ?
C15 N11 C18 N1 159.8(2) . . . . ?
N12 N11 C18 N1 -32.4(3) . . . . ?
C22 C21 C22 C23 -0.4(6) 4_565 . . . ?
C25 C21 C22 C23 -179.2(4) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C22 C23 C24 C23 -0.4(7) . . . 4_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16A O1 0.96 2.45 3.181(4) 133.2 .
C22 H22 S2 0.93 3.09 3.799(3) 134.0 3_556

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045



