# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_VMOP_18
_database_code_depnum_ccdc_archive 'CCDC 1849691'
_audit_update_record             
;
2018-06-23 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C132 H156 N12 O100 V28'
_chemical_formula_sum            'C164 H284 N16 O124 V28'
_chemical_formula_weight         5890.37

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      cubic
_space_group_IT_number           217
_space_group_name_H-M_alt        'I -4 3 m'
_space_group_name_Hall           'I -4 2 3'

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

_cell_length_a                   27.796(4)
_cell_length_b                   27.796(4)
_cell_length_c                   27.796(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     21476(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2402
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      22.92

_exptl_crystal_description       block
_exptl_crystal_colour            reddishbrown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    0.911
_exptl_crystal_F_000             6032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.633
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_process_details   'SADABS 2014/4 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ω-2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22229
_diffrn_reflns_av_unetI/netI     0.1024
_diffrn_reflns_av_R_equivalents  0.1630
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.317
_diffrn_reflns_theta_max         25.162
_diffrn_reflns_theta_full        25.162
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3467
_reflns_number_gt                2008
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.989

_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 APEX 2'
_computing_cell_refinement       'Bruker SAINT v8.34a'
_computing_data_reduction        'Bruker SAINT v8.34a'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1853P)²+81.9784P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.325(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3467
_refine_ls_number_parameters     132
_refine_ls_number_restraints     263
_refine_ls_R_factor_all          0.1878
_refine_ls_R_factor_gt           0.1180
_refine_ls_wR_factor_ref         0.3751
_refine_ls_wR_factor_gt          0.3054
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.002
_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 0.27138(2) 0.64988(2) 0.18682(2) 0.11222(3) Uani 1 1 d . U . . .
O1 O 0.27631(2) 0.58352(2) 0.22050(2) 0.10917(8) Uani 1 1 d . U . . .
O2 O 0.34329(2) 0.65671(2) 0.19380(2) 0.11462(11) Uani 1 2 d DS TU P . .
O3 O 0.26544(2) 0.62838(2) 0.13470(2) 0.14188(16) Uani 1 1 d . U . . .
O4 O 0.28145(2) 0.71855(2) 0.17408(2) 0.11835(12) Uani 1 2 d S TU P . .
O5 O 0.20208(2) 0.65318(2) 0.20208(2) 0.11785(11) Uani 1 2 d S TU P . .
O6 O 0.26324(2) 0.67462(2) 0.26324(2) 0.10866(10) Uani 1 2 d S TU P . .
O7 O 0.33222(2) 0.66778(2) 0.33222(2) 0.1421(3) Uani 1 6 d S TU P . .
N007 N 0.31436(2) 0.37342(2) 0.37342(2) 0.06766(14) Uani 1 2 d S T P . .
C1 C 0.33497(2) 0.39313(3) 0.33497(2) 0.09183(13) Uani 1 2 d S TU P . .
C2 C 0.31387(2) 0.43766(2) 0.31387(2) 0.09678(12) Uani 1 2 d DS TU P . .
C3 C 0.27361(2) 0.45820(2) 0.33473(2) 0.09888(10) Uani 1 1 d D U . . .
H3 H 0.26428(7) 0.44881(8) 0.35204(14) 0.119 Uiso 1 1 calc R U . . .
C4 C 0.25475(2) 0.50021(2) 0.31595(2) 0.09983(10) Uani 1 1 d D U . . .
H4 H 0.227858 0.514614 0.329690 0.120 Uiso 1 1 calc R U . . .
C5 C 0.27667(2) 0.52000(2) 0.27667(2) 0.09890(11) Uani 1 2 d DS TU P . .
C6 C 0.26053(2) 0.56531(2) 0.26053(2) 0.10809(10) Uani 1 2 d DS TU P . .
C7 C 0.16392(3) 0.64559(4) 0.16392(3) 0.1627(3) Uani 1 2 d S TU P . .
H7A H 0.174251 0.620935 0.142052 0.244 Uiso 0.5 1 calc R U P A -1
H7B H 0.158976 0.675038 0.146566 0.244 Uiso 0.5 1 calc R U P A -1
H7C H 0.134350 0.635987 0.178959 0.244 Uiso 0.5 1 calc R U P A -1
C8 C 0.24906(2) 0.75094(2) 0.14557(3) 0.1412(3) Uani 1 2 d S TU P . .
H8A H 0.262074 0.755229 0.113868 0.212 Uiso 0.5 1 calc R U P B -1
H8B H 0.246704 0.781602 0.161292 0.212 Uiso 0.5 1 calc R U P B -1
H8C H 0.217665 0.736726 0.143301 0.212 Uiso 0.5 1 calc R U P B -1
C9 C 0.37888(2) 0.62112(2) 0.20073(4) 0.1343(3) Uani 1 2 d DS TU P . .
H9A H 0.402439 0.623347 0.175572 0.202 Uiso 0.5 1 calc R U P C -1
H9B H 0.364199 0.589867 0.200018 0.202 Uiso 0.5 1 calc R U P C -1
H9C H 0.394195 0.625953 0.231304 0.202 Uiso 0.5 1 calc R U P C -1
V3 V 0.29802(2) 0.70198(2) 0.29802(2) 0.15267(14) Uani 0.6667 6 d S TU P . 2
V2 V 0.27058(2) 0.72942(2) 0.27058(2) 0.1653(2) Uani 0.3334 6 d S TU P . 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O3 1.5758(5) . ?
V1 O4 1.9614(4) . ?
V1 O5 1.9746(4) . ?
V1 O2 2.0172(4) . ?
V1 O1 2.0730(4) . ?
V1 O6 2.2442(4) . ?
V1 V1 3.0953(5) 14_665 ?
O1 C6 1.2988(5) . ?
O2 C9 1.4122(8) . ?
O4 C8 1.4998(10) . ?
O5 C7 1.5148(11) . ?
O6 V2 1.5503(7) . ?
O6 V3 1.5645(6) . ?
O7 V3 1.6465(13) . ?
N007 C1 1.3306(5) 5 ?
N007 C1 1.3306(5) . ?
C1 C2 1.4900(10) . ?
C2 C3 1.3836(5) 21 ?
C2 C3 1.3837(5) . ?
C3 C4 1.3823(6) . ?
C4 C5 1.3660(5) . ?
C5 C6 1.4102(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 V1 O4 102.59(2) . . ?
O3 V1 O5 96.48(2) . . ?
O4 V1 O5 97.63(2) . . ?
O3 V1 O2 103.18(2) . . ?
O4 V1 O2 77.547(15) . . ?
O5 V1 O2 160.329(19) . . ?
O3 V1 O1 94.85(2) . . ?
O4 V1 O1 159.718(17) . . ?
O5 V1 O1 90.505(18) . . ?
O2 V1 O1 88.556(15) . . ?
O3 V1 O6 167.38(2) . . ?
O4 V1 O6 83.52(2) . . ?
O5 V1 O6 71.583(15) . . ?
O2 V1 O6 88.855(17) . . ?
O1 V1 O6 81.483(16) . . ?
O3 V1 V1 110.015(18) . 14_665 ?
O4 V1 V1 37.904(11) . 14_665 ?
O5 V1 V1 131.068(15) . 14_665 ?
O2 V1 V1 39.895(10) . 14_665 ?
O1 V1 V1 125.622(10) . 14_665 ?
O6 V1 V1 81.640(10) . 14_665 ?
C6 O1 V1 135.34(3) . . ?
C9 O2 V1 129.890(10) . . ?
C9 O2 V1 129.890(10) . 14_665 ?
V1 O2 V1 100.211(19) . 14_665 ?
C8 O4 V1 126.438(15) . . ?
C8 O4 V1 126.436(15) . 14_665 ?
V1 O4 V1 104.19(2) . 14_665 ?
C7 O5 V1 121.750(13) . 21 ?
C7 O5 V1 121.749(14) . . ?
V1 O5 V1 114.64(2) 21 . ?
V2 O6 V1 114.35(3) . 21 ?
V2 O6 V1 114.35(3) . . ?
V3 O6 V1 132.188(9) . . ?
V1 O6 V1 95.563(18) 21 . ?
C1 N007 C1 118.43(7) 5 . ?
N007 C1 N007 121.47(7) 9 . ?
N007 C1 C2 119.26(3) 9 . ?
N007 C1 C2 119.26(3) . . ?
C3 C2 C3 120.51(6) 21 . ?
C3 C2 C1 119.75(3) 21 . ?
C3 C2 C1 119.75(3) . . ?
C4 C3 C2 119.80(4) . . ?
C5 C4 C3 118.22(4) . . ?
C4 C5 C4 123.43(5) 21 . ?
C4 C5 C6 118.16(3) 21 . ?
C4 C5 C6 118.17(3) . . ?
O1 C6 O1 115.26(6) 21 . ?
O1 C6 C5 120.88(3) 21 . ?
O1 C6 C5 120.88(3) . . ?
O6 V3 O6 102.64(3) . 12_665 ?
O6 V3 O6 102.64(3) . 6_566 ?
O6 V3 O6 102.64(3) 12_665 6_566 ?
O6 V3 O7 115.65(3) . . ?
O6 V3 O7 115.65(3) 12_665 . ?
O6 V3 O7 115.65(3) 6_566 . ?
O6 V2 O6 103.97(5) 12_665 6_566 ?
O6 V2 O6 103.96(5) 12_665 . ?
O6 V2 O6 103.96(5) 6_566 . ?

_refine_diff_density_max         0.930
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.080



####################################################################### 
# 
# 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_VMOP_19
_database_code_depnum_ccdc_archive 'CCDC 1849692'
_audit_update_record             
;
2018-06-15 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;
_audit_creation_date             2018-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C132 H156 N12 O100 S4 V24'
_chemical_formula_sum            'C156 H252 N20 O108 S4 V24'
_chemical_formula_weight         5486.56
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      cubic
_space_group_IT_number           217
_space_group_name_H-M_alt        'I -4 3 m'
_space_group_name_Hall           'I -4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x, -y, -z'
'-x, y, -z'
'z, x, y'
'y, z, x'
'-z, -x, y'
'-y, z, -x'
'z, -x, -y'
'-y, -z, x'
'-z, x, -y'
'y, -z, -x'
'y, x, z'
'-y, -x, z'
'-y, x, -z'
'y, -x, -z'
'x, z, y'
'z, y, x'
'-x, -z, y'
'z, -y, -x'
'-x, z, -y'
'-z, -y, x'
'x, -z, -y'
'-z, y, -x'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'z+1/2, x+1/2, y+1/2'
'y+1/2, z+1/2, x+1/2'
'-z+1/2, -x+1/2, y+1/2'
'-y+1/2, z+1/2, -x+1/2'
'z+1/2, -x+1/2, -y+1/2'
'-y+1/2, -z+1/2, x+1/2'
'-z+1/2, x+1/2, -y+1/2'
'y+1/2, -z+1/2, -x+1/2'
'y+1/2, x+1/2, z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'x+1/2, z+1/2, y+1/2'
'z+1/2, y+1/2, x+1/2'
'-x+1/2, -z+1/2, y+1/2'
'z+1/2, -y+1/2, -x+1/2'
'-x+1/2, z+1/2, -y+1/2'
'-z+1/2, -y+1/2, x+1/2'
'x+1/2, -z+1/2, -y+1/2'
'-z+1/2, y+1/2, -x+1/2'

_cell_length_a                   27.216(2)
_cell_length_b                   27.216(2)
_cell_length_c                   27.216(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     20160(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2476
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      50.000
_cell_measurement_theta_min      1.953
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.904
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5616
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1882
_diffrn_reflns_av_unetI/netI     0.1452
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20608
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.030
_diffrn_reflns_theta_max         25.030
_diffrn_reflns_theta_min         2.592
_diffrn_ambient_temperature      173.05
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1273
_reflns_number_total             3270
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.24(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     360
_refine_ls_R_factor_all          0.2099
_refine_ls_R_factor_gt           0.1055
_refine_ls_restrained_S_all      0.973
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1877P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2581
_refine_ls_wR_factor_ref         0.3285
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.76(13)
 0.24(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O2-C10
 1.4 with sigma of 0.02
 C6-C5 = C5-C4 = C4-C3 = C3-C2 = N1-C2
 1.38 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10
\\sim O1 \\sim O2 \\sim O3 \\sim O4 \\sim O5 \\sim O6 \\sim O7 \\sim S1 \\sim
V1: within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.03
5. Others
 Fixed Sof: H8A(0.5) H8B(0.5) H8C(0.5) H9A(0.5) H9B(0.5) H9C(0.5) H10A(0.5)
 H10B(0.5) H10C(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
6.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.67934(12) 0.23296(13) 0.15185(15) 0.1606(18) Uani 1 1 d . U . . .
S1 S 0.79226(19) 0.20774(19) 0.20774(19) 0.143(3) Uani 1 6 d S TU P . .
O1 O 0.7150(4) 0.2266(4) 0.0876(4) 0.141(3) Uani 1 1 d . U . . .
O2 O 0.6971(3) 0.3029(3) 0.1605(7) 0.158(3) Uani 1 2 d DS TU P . .
O3 O 0.6269(5) 0.2372(5) 0.1331(5) 0.179(5) Uani 1 1 d . U . . .
O4 O 0.6656(6) 0.2198(5) 0.2198(5) 0.160(3) Uani 1 2 d S TU P . .
O5 O 0.7601(3) 0.2399(3) 0.1771(6) 0.144(3) Uani 1 2 d S TU P . .
O6 O 0.6878(5) 0.1620(4) 0.1620(4) 0.149(3) Uani 1 2 d S TU P . .
O7 O 0.8211(4) 0.1789(4) 0.1789(4) 0.119(6) Uani 1 6 d S TU P . .
N1 N 0.8783(4) 0.1830(6) -0.1217(4) 0.120(6) Uani 1 2 d DS T P . .
C2 C 0.8381(5) 0.1619(5) -0.1007(7) 0.116(4) Uani 1 2 d DS TU P . .
C3 C 0.8183(5) 0.1817(5) -0.0590(7) 0.113(4) Uani 1 2 d DS TU P . .
C4 C 0.8347(5) 0.2239(5) -0.0380(5) 0.121(4) Uani 1 1 d D U . . .
H4 H 0.861610 0.240116 -0.053284 0.145 Uiso 1 1 calc R . . . .
C5 C 0.8156(5) 0.2445(5) 0.0030(5) 0.123(3) Uani 1 1 d D U . . .
H5 H 0.830715 0.272753 0.016972 0.148 Uiso 1 1 calc R . . . .
C6 C 0.7750(5) 0.2250(5) 0.0241(8) 0.123(4) Uani 1 2 d DS TU P . .
C7 C 0.7534(6) 0.2466(6) 0.0688(10) 0.139(3) Uani 1 2 d S TU P . .
C8 C 0.7080(9) 0.1266(7) 0.1266(7) 0.152(7) Uani 1 2 d S TU P . .
H8A H 0.684936 0.122546 0.099285 0.228 Uiso 0.5 1 calc GR . . A -1
H8B H 0.713039 0.094926 0.142929 0.228 Uiso 0.5 1 calc GR . . A -1
H8C H 0.739462 0.138831 0.114089 0.228 Uiso 0.5 1 calc GR . . A -1
C9 C 0.6365(12) 0.2539(7) 0.2539(7) 0.178(8) Uani 1 2 d S TU P . .
H9A H 0.658833 0.268794 0.277862 0.267 Uiso 0.5 1 calc GR . . B -1
H9B H 0.611280 0.234863 0.271159 0.267 Uiso 0.5 1 calc GR . . B -1
H9C H 0.620785 0.279754 0.234390 0.267 Uiso 0.5 1 calc GR . . B -1
C10 C 0.6585(5) 0.3415(5) 0.1738(12) 0.195(9) Uani 1 2 d DS TU P . .
H10A H 0.631926 0.340877 0.149504 0.293 Uiso 0.5 1 calc GR . . C -1
H10B H 0.673701 0.374161 0.174091 0.293 Uiso 0.5 1 calc GR . . C -1
H10C H 0.645024 0.334311 0.206450 0.293 Uiso 0.5 1 calc GR . . C -1


_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 2.007(11) . ?
V1 O2 1.978(7) . ?
V1 O3 1.520(13) . ?
V1 O4 1.920(9) . ?
V1 O5 2.312(12) . ?
V1 O6 1.965(10) . ?
S1 O5 1.491(16) . ?
S1 O5 1.491(16) 7_665 ?
S1 O5 1.491(16) 8_656 ?
S1 O7 1.36(2) . ?
O1 C7 1.284(14) . ?
O2 C10 1.53(2) . ?
O4 C9 1.53(3) . ?
O6 C8 1.47(3) . ?
N1 C2 1.360(9) 9_665 ?
N1 C2 1.360(9) . ?
C2 C3 1.367(13) . ?
C3 C4 1.358(11) 14_665 ?
C3 C4 1.358(11) . ?
C4 C5 1.354(12) . ?
C5 C6 1.355(11) . ?
C6 C7 1.47(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O5 78.8(5) . . ?
O2 V1 O1 93.9(6) . . ?
O2 V1 O5 69.8(5) . . ?
O3 V1 O1 99.7(6) . . ?
O3 V1 O2 101.3(7) . . ?
O3 V1 O4 99.0(7) . . ?
O3 V1 O5 170.7(7) . . ?
O3 V1 O6 103.5(8) . . ?
O4 V1 O1 156.4(5) . . ?
O4 V1 O2 96.5(7) . . ?
O4 V1 O5 85.0(7) . . ?
O4 V1 O6 72.8(5) . . ?
O6 V1 O1 88.9(5) . . ?
O6 V1 O2 154.3(6) . . ?
O6 V1 O5 85.8(6) . . ?
O5 S1 O5 108.2(7) 8_656 . ?
O5 S1 O5 108.2(7) 7_665 . ?
O5 S1 O5 108.2(7) 7_665 8_656 ?
O7 S1 O5 110.7(6) . . ?
O7 S1 O5 110.7(6) . 8_656 ?
O7 S1 O5 110.7(6) . 7_665 ?
C7 O1 V1 134.8(15) . . ?
V1 O2 V1 117.1(6) 14_665 . ?
C10 O2 V1 121.4(3) . . ?
C10 O2 V1 121.4(3) . 14_665 ?
V1 O4 V1 108.8(8) . 17 ?
C9 O4 V1 124.7(4) . . ?
C9 O4 V1 124.7(4) . 17 ?
V1 O5 V1 93.8(6) . 14_665 ?
S1 O5 V1 132.6(4) . . ?
S1 O5 V1 132.6(4) . 14_665 ?
V1 O6 V1 105.2(7) . 17 ?
C8 O6 V1 126.6(3) . . ?
C8 O6 V1 126.6(3) . 17 ?
C2 N1 C2 120(2) 9_665 . ?
N1 C2 N1 120(2) 10_654 . ?
N1 C2 C3 120.0(11) 10_654 . ?
N1 C2 C3 120.0(11) . . ?
C4 C3 C2 123.5(10) 14_665 . ?
C4 C3 C2 123.5(10) . . ?
C4 C3 C4 112.3(19) 14_665 . ?
C5 C4 C3 124.8(17) . . ?
C4 C5 C6 120.0(18) . . ?
C5 C6 C5 117(2) . 14_665 ?
C5 C6 C7 121.3(11) . . ?
C5 C6 C7 121.3(11) 14_665 . ?
O1 C7 O1 122(2) 14_665 . ?
O1 C7 C6 119.0(12) . . ?
O1 C7 C6 119.0(12) 14_665 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
V1 O1 C7 O1 -13(4) . . . 14_665 ?
V1 O1 C7 C6 167.1(13) . . . . ?
O5 S1 O5 V1 -140.9(3) 7_665 . . . ?
O5 S1 O5 V1 -23.9(17) 8_656 . . . ?
O5 S1 O5 V1 23.9(17) 7_665 . . 14_665 ?
O5 S1 O5 V1 140.9(3) 8_656 . . 14_665 ?
O7 S1 O5 V1 97.6(10) . . . . ?
O7 S1 O5 V1 -97.6(10) . . . 14_665 ?
N1 C2 C3 C4 4(3) . . . . ?
N1 C2 C3 C4 174.5(18) . . . 14_665 ?
N1 C2 C3 C4 -174.5(18) 10_654 . . . ?
N1 C2 C3 C4 -4(3) 10_654 . . 14_665 ?
C2 N1 C2 N1 -5(4) 9_665 . . 10_654 ?
C2 N1 C2 C3 176.8(12) 9_665 . . . ?
C2 C3 C4 C5 179.4(17) . . . . ?
C3 C4 C5 C6 -5(2) . . . . ?
C4 C3 C4 C5 8(3) 14_665 . . . ?
C4 C5 C6 C5 1(3) . . . 14_665 ?
C4 C5 C6 C7 179.9(17) . . . . ?
C5 C6 C7 O1 -179.7(18) . . . . ?
C5 C6 C7 O1 1(3) . . . 14_665 ?
C5 C6 C7 O1 179.7(18) 14_665 . . 14_665 ?
C5 C6 C7 O1 -1(3) 14_665 . . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.010 -0.036 -0.015 12832 2546 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.76(13)
2 0.24(13)

