# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_compound01
_database_code_depnum_ccdc_archive 'CCDC 1058755'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2015-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H28 N2 O5 Se Si'
_chemical_formula_sum            'C17 H28 N2 O5 Se Si'
_chemical_formula_weight         447.46

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   7.621(2)
_cell_length_b                   13.163(4)
_cell_length_c                   23.299(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2337.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2924
_cell_measurement_theta_min      3.0455
_cell_measurement_theta_max      27.4662

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    1.683
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7295
_exptl_absorpt_correction_T_max  0.7295
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 14.6199
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18705
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5295
_reflns_number_gt                2950
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CRYSTALCLEAR
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_reduction        CRYSTALCLEAR
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material  
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1617P)²+0.9922P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_number_reflns         5295
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1599
_refine_ls_R_factor_gt           0.1062
_refine_ls_wR_factor_ref         0.3156
_refine_ls_wR_factor_gt          0.2754
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1475(15) 0.5829(8) 0.1166(5) 0.083(3) Uani 1 1 d . . .
N1 N 1.0268(11) 0.6260(6) 0.0773(4) 0.081(2) Uani 1 1 d . . .
H1 H 0.9497 0.5856 0.0629 0.097 Uiso 1 1 calc R . .
C2 C 1.0199(13) 0.7285(8) 0.0590(5) 0.077(3) Uani 1 1 d . . .
N2 N 1.1479(10) 0.7941(6) 0.0833(4) 0.072(2) Uani 1 1 d . . .
C3 C 1.2697(14) 0.7566(8) 0.1238(5) 0.082(3) Uani 1 1 d . . .
H3 H 1.3494 0.8019 0.1399 0.099 Uiso 1 1 calc R . .
C4 C 1.2766(16) 0.6576(8) 0.1406(5) 0.094(3) Uani 1 1 d . . .
H4 H 1.3611 0.6364 0.1668 0.112 Uiso 1 1 calc R . .
O1 O 1.1403(11) 0.4887(6) 0.1264(4) 0.104(2) Uani 1 1 d . . .
O2 O 0.9009(8) 0.7612(5) 0.0253(3) 0.0812(19) Uani 1 1 d . . .
C5 C 1.1523(12) 0.9053(7) 0.0698(4) 0.072(3) Uani 1 1 d . . .
H5 H 1.2677 0.9311 0.0813 0.087 Uiso 1 1 calc R . .
C6 C 1.1231(11) 0.9360(7) 0.0040(4) 0.069(2) Uani 1 1 d . . .
H6 H 1.1095 0.8765 -0.0208 0.082 Uiso 1 1 calc R . .
C7 C 0.9529(11) 1.0046(7) 0.0049(5) 0.077(3) Uani 1 1 d . . .
H7 H 0.8624 0.9795 -0.0214 0.093 Uiso 1 1 calc R . .
C8 C 0.8848(11) 1.0127(7) 0.0681(5) 0.075(2) Uani 1 1 d . . .
H8 H 0.8825 1.0846 0.0791 0.089 Uiso 1 1 calc R . .
O3 O 1.0203(7) 0.9599(5) 0.1033(3) 0.0730(16) Uani 1 1 d . . .
O4 O 1.2636(8) 1.0016(5) -0.0148(3) 0.080(2) Uani 1 1 d . . .
O5 O 1.0232(11) 1.1046(6) -0.0132(4) 0.102(3) Uani 1 1 d . . .
C9 C 1.1841(13) 1.0869(7) -0.0460(5) 0.077(3) Uani 1 1 d . . .
C10 C 1.307(2) 1.1803(10) -0.0378(7) 0.125(5) Uani 1 1 d . . .
H10 H 1.2449 1.2414 -0.0470 0.188 Uiso 1 1 calc R . .
H10A H 1.4073 1.1738 -0.0626 0.188 Uiso 1 1 calc R . .
H10B H 1.3462 1.1831 0.0014 0.188 Uiso 1 1 calc R . .
C11 C 1.1482(16) 1.0589(11) -0.1081(5) 0.103(4) Uani 1 1 d . . .
H11 H 1.0810 0.9973 -0.1096 0.154 Uiso 1 1 calc R . .
H11A H 1.2575 1.0491 -0.1279 0.154 Uiso 1 1 calc R . .
H11B H 1.0835 1.1126 -0.1263 0.154 Uiso 1 1 calc R . .
C12 C 0.7002(12) 0.9661(10) 0.0797(4) 0.082(3) Uani 1 1 d . . .
H12 H 0.7021 0.8955 0.0678 0.099 Uiso 1 1 calc R . .
H12A H 0.6155 1.0010 0.0556 0.099 Uiso 1 1 calc R . .
Se1 Se 0.61803(12) 0.97250(9) 0.15933(5) 0.0855(4) Uani 1 1 d . . .
C13 C 0.7427(14) 0.8500(11) 0.1897(5) 0.103(4) Uani 1 1 d . . .
H13 H 0.7193 0.7923 0.1649 0.123 Uiso 1 1 calc R . .
H13A H 0.8682 0.8623 0.1896 0.123 Uiso 1 1 calc R . .
C14 C 0.6801(17) 0.8253(12) 0.2524(5) 0.103(4) Uani 1 1 d . . .
H14 H 0.5575 0.8056 0.2514 0.124 Uiso 1 1 calc R . .
H14A H 0.6892 0.8864 0.2756 0.124 Uiso 1 1 calc R . .
Si1 Si 0.8139(5) 0.7182(3) 0.28874(15) 0.0920(10) Uani 1 1 d . . .
C15 C 0.794(2) 0.5907(14) 0.2484(6) 0.134(6) Uani 1 1 d . . .
H15 H 0.8561 0.5389 0.2693 0.201 Uiso 1 1 calc R . .
H15A H 0.8445 0.5974 0.2108 0.201 Uiso 1 1 calc R . .
H15B H 0.6730 0.5722 0.2451 0.201 Uiso 1 1 calc R . .
C16 C 0.7238(19) 0.7055(11) 0.3644(6) 0.112(4) Uani 1 1 d . . .
H16 H 0.7463 0.7669 0.3853 0.168 Uiso 1 1 calc R . .
H16A H 0.7800 0.6495 0.3833 0.168 Uiso 1 1 calc R . .
H16B H 0.5996 0.6936 0.3627 0.168 Uiso 1 1 calc R . .
C17 C 1.0557(18) 0.7554(13) 0.2927(7) 0.123(5) Uani 1 1 d . . .
H17 H 1.0656 0.8239 0.3064 0.185 Uiso 1 1 calc R . .
H17A H 1.1071 0.7506 0.2551 0.185 Uiso 1 1 calc R . .
H17B H 1.1159 0.7104 0.3184 0.185 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.262(12) . ?
C1 N1 1.418(14) . ?
C1 C4 1.499(15) . ?
N1 C2 1.416(13) . ?
N1 H1 0.8600 . ?
C2 O2 1.275(12) . ?
C2 N2 1.421(13) . ?
N2 C3 1.413(12) . ?
N2 C5 1.498(12) . ?
C3 C4 1.361(15) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 O3 1.463(11) . ?
C5 C6 1.600(13) . ?
C5 H5 0.9800 . ?
C6 O4 1.444(10) . ?
C6 C7 1.581(13) . ?
C6 H6 0.9800 . ?
C7 O5 1.482(12) . ?
C7 C8 1.565(14) . ?
C7 H7 0.9800 . ?
C8 O3 1.491(11) . ?
C8 C12 1.558(12) . ?
C8 H8 0.9800 . ?
O4 C9 1.469(11) . ?
O5 C9 1.464(12) . ?
C9 C11 1.518(16) . ?
C9 C10 1.560(16) . ?
C10 H10 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C11 H11 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C12 Se1 1.960(10) . ?
C12 H12 0.9700 . ?
C12 H12A 0.9700 . ?
Se1 C13 2.000(13) . ?
C13 C14 1.572(15) . ?
C13 H13 0.9700 . ?
C13 H13A 0.9700 . ?
C14 Si1 1.935(14) . ?
C14 H14 0.9700 . ?
C14 H14A 0.9700 . ?
Si1 C16 1.899(13) . ?
Si1 C17 1.909(15) . ?
Si1 C15 1.929(16) . ?
C15 H15 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C16 H16 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C17 H17 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 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 C1 N1 118.8(11) . . ?
O1 C1 C4 127.3(11) . . ?
N1 C1 C4 113.9(8) . . ?
C1 N1 C2 126.9(9) . . ?
C1 N1 H1 116.6 . . ?
C2 N1 H1 116.6 . . ?
O2 C2 N2 121.9(9) . . ?
O2 C2 N1 122.3(9) . . ?
N2 C2 N1 115.7(9) . . ?
C3 N2 C2 120.3(8) . . ?
C3 N2 C5 117.9(8) . . ?
C2 N2 C5 121.7(8) . . ?
C4 C3 N2 123.5(10) . . ?
C4 C3 H3 118.3 . . ?
N2 C3 H3 118.3 . . ?
C3 C4 C1 119.7(10) . . ?
C3 C4 H4 120.1 . . ?
C1 C4 H4 120.1 . . ?
O3 C5 N2 110.6(7) . . ?
O3 C5 C6 107.0(7) . . ?
N2 C5 C6 116.5(8) . . ?
O3 C5 H5 107.5 . . ?
N2 C5 H5 107.5 . . ?
C6 C5 H5 107.5 . . ?
O4 C6 C7 105.7(6) . . ?
O4 C6 C5 109.8(7) . . ?
C7 C6 C5 104.2(7) . . ?
O4 C6 H6 112.2 . . ?
C7 C6 H6 112.2 . . ?
C5 C6 H6 112.2 . . ?
O5 C7 C6 102.0(7) . . ?
O5 C7 C8 109.1(8) . . ?
C6 C7 C8 108.9(8) . . ?
O5 C7 H7 112.1 . . ?
C6 C7 H7 112.1 . . ?
C8 C7 H7 112.1 . . ?
O3 C8 C12 110.3(8) . . ?
O3 C8 C7 104.9(7) . . ?
C12 C8 C7 115.8(8) . . ?
O3 C8 H8 108.5 . . ?
C12 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C5 O3 C8 114.2(7) . . ?
C6 O4 C9 107.5(7) . . ?
C9 O5 C7 108.0(7) . . ?
O5 C9 O4 102.0(8) . . ?
O5 C9 C11 112.7(9) . . ?
O4 C9 C11 111.2(9) . . ?
O5 C9 C10 108.3(9) . . ?
O4 C9 C10 107.0(10) . . ?
C11 C9 C10 114.6(10) . . ?
C9 C10 H10 109.5 . . ?
C9 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C11 H11 109.5 . . ?
C9 C11 H11A 109.5 . . ?
H11 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C12 Se1 115.8(7) . . ?
C8 C12 H12 108.3 . . ?
Se1 C12 H12 108.3 . . ?
C8 C12 H12A 108.3 . . ?
Se1 C12 H12A 108.3 . . ?
H12 C12 H12A 107.4 . . ?
C12 Se1 C13 98.5(5) . . ?
C14 C13 Se1 110.6(9) . . ?
C14 C13 H13 109.5 . . ?
Se1 C13 H13 109.5 . . ?
C14 C13 H13A 109.5 . . ?
Se1 C13 H13A 109.5 . . ?
H13 C13 H13A 108.1 . . ?
C13 C14 Si1 113.4(10) . . ?
C13 C14 H14 108.9 . . ?
Si1 C14 H14 108.9 . . ?
C13 C14 H14A 108.9 . . ?
Si1 C14 H14A 108.9 . . ?
H14 C14 H14A 107.7 . . ?
C16 Si1 C17 109.1(7) . . ?
C16 Si1 C14 106.2(6) . . ?
C17 Si1 C14 110.0(7) . . ?
C16 Si1 C15 110.4(6) . . ?
C17 Si1 C15 108.7(8) . . ?
C14 Si1 C15 112.4(8) . . ?
Si1 C15 H15 109.5 . . ?
Si1 C15 H15A 109.5 . . ?
H15 C15 H15A 109.5 . . ?
Si1 C15 H15B 109.5 . . ?
H15 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si1 C16 H16 109.5 . . ?
Si1 C16 H16A 109.5 . . ?
H16 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C17 H17 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
H17 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
H17 C17 H17B 109.5 . . ?
H17A C17 H17B 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
O1 C1 N1 C2 -176.9(11) . . . . ?
C4 C1 N1 C2 0.8(16) . . . . ?
C1 N1 C2 O2 -176.7(10) . . . . ?
C1 N1 C2 N2 -0.2(16) . . . . ?
O2 C2 N2 C3 175.3(10) . . . . ?
N1 C2 N2 C3 -1.2(14) . . . . ?
O2 C2 N2 C5 -1.1(15) . . . . ?
N1 C2 N2 C5 -177.6(9) . . . . ?
C2 N2 C3 C4 2.1(16) . . . . ?
C5 N2 C3 C4 178.6(11) . . . . ?
N2 C3 C4 C1 -1.4(19) . . . . ?
O1 C1 C4 C3 177.5(12) . . . . ?
N1 C1 C4 C3 0.0(17) . . . . ?
C3 N2 C5 O3 -97.0(10) . . . . ?
C2 N2 C5 O3 79.5(11) . . . . ?
C3 N2 C5 C6 140.5(8) . . . . ?
C2 N2 C5 C6 -43.0(12) . . . . ?
O3 C5 C6 O4 108.1(8) . . . . ?
N2 C5 C6 O4 -127.6(8) . . . . ?
O3 C5 C6 C7 -4.8(9) . . . . ?
N2 C5 C6 C7 119.5(8) . . . . ?
O4 C6 C7 O5 -1.1(10) . . . . ?
C5 C6 C7 O5 114.6(8) . . . . ?
O4 C6 C7 C8 -116.3(8) . . . . ?
C5 C6 C7 C8 -0.5(9) . . . . ?
O5 C7 C8 O3 -105.0(8) . . . . ?
C6 C7 C8 O3 5.5(9) . . . . ?
O5 C7 C8 C12 133.2(9) . . . . ?
C6 C7 C8 C12 -116.3(9) . . . . ?
N2 C5 O3 C8 -118.8(8) . . . . ?
C6 C5 O3 C8 9.0(9) . . . . ?
C12 C8 O3 C5 116.2(9) . . . . ?
C7 C8 O3 C5 -9.2(9) . . . . ?
C7 C6 O4 C9 -22.1(10) . . . . ?
C5 C6 O4 C9 -134.0(8) . . . . ?
C6 C7 O5 C9 24.1(11) . . . . ?
C8 C7 O5 C9 139.1(8) . . . . ?
C7 O5 C9 O4 -37.8(10) . . . . ?
C7 O5 C9 C11 81.6(11) . . . . ?
C7 O5 C9 C10 -150.5(10) . . . . ?
C6 O4 C9 O5 36.8(10) . . . . ?
C6 O4 C9 C11 -83.7(10) . . . . ?
C6 O4 C9 C10 150.4(9) . . . . ?
O3 C8 C12 Se1 59.3(10) . . . . ?
C7 C8 C12 Se1 178.2(7) . . . . ?
C8 C12 Se1 C13 -82.6(9) . . . . ?
C12 Se1 C13 C14 -171.8(8) . . . . ?
Se1 C13 C14 Si1 -172.9(6) . . . . ?
C13 C14 Si1 C16 177.5(9) . . . . ?
C13 C14 Si1 C17 59.5(11) . . . . ?
C13 C14 Si1 C15 -61.8(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.900
_refine_diff_density_rms         0.106
