# 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_mks60m
_database_code_depnum_ccdc_archive 'CCDC 1042109'
_audit_update_record             
;
2015-01-05 deposited with the CCDC.
2015-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H25 N O6'
_chemical_formula_sum            'C20 H25 N O6'
_chemical_melting_point          ?

_exptl_crystal_description       rod
_exptl_crystal_colour            white

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         375.41

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
_chemical_absolute_configuration syn

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

_cell_length_a                   9.0447(15)
_cell_length_b                   11.7121(19)
_cell_length_c                   18.619(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1972.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3825
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      28.320
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      1.264
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800.0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0938
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23136
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         28.32
_reflns_number_total             4772
_reflns_number_gt                3825
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0886P)²+0.1111P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   0.2(11)
_refine_ls_number_reflns         4772
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1471
_refine_ls_wR_factor_gt          0.1380
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
O5 O 0.91726(16) 0.45441(15) 0.12433(7) 0.0664(4) Uani 1 1 d . . .
O3 O 1.17178(16) 0.58101(11) -0.09582(8) 0.0610(3) Uani 1 1 d . . .
C10 C 1.1350(2) 0.15288(16) 0.04985(11) 0.0547(4) Uani 1 1 d . . .
O4 O 1.17021(15) 0.34866(11) 0.03051(8) 0.0650(4) Uani 1 1 d . . .
C3 C 1.1207(2) 0.45234(15) -0.00074(10) 0.0525(4) Uani 1 1 d . . .
H3 H 1.0275 0.4417 -0.0267 0.063 Uiso 1 1 calc R . .
O1 O 1.25346(17) 0.58934(13) 0.06461(8) 0.0669(4) Uani 1 1 d . . .
O6 O 1.0929(2) 0.14987(13) 0.11861(8) 0.0738(4) Uani 1 1 d . . .
C11 C 1.2093(2) 0.05854(15) 0.03376(10) 0.0541(4) Uani 1 1 d . . .
H11 H 1.2505 0.0391 -0.0103 0.065 Uiso 1 1 calc R . .
C2 C 1.2387(2) 0.50159(15) -0.04870(10) 0.0539(4) Uani 1 1 d . . .
H2 H 1.2963 0.4430 -0.0738 0.065 Uiso 1 1 calc R . .
O2 O 1.35068(18) 0.67827(13) -0.03636(9) 0.0734(4) Uani 1 1 d . . .
C1 C 1.3322(2) 0.57574(16) 0.00050(11) 0.0567(4) Uani 1 1 d . . .
H1 H 1.4281 0.5396 0.0097 0.068 Uiso 1 1 calc R . .
C4 C 1.1066(2) 0.54471(17) 0.05682(11) 0.0567(4) Uani 1 1 d . . .
H4 H 1.0396 0.6050 0.0403 0.068 Uiso 1 1 calc R . .
C15 C 0.73425(15) 0.34235(15) 0.18481(8) 0.0684(5) Uani 1 1 d G . .
C16 C 0.6084(2) 0.40830(13) 0.17397(10) 0.0857(7) Uani 1 1 d G . .
H16 H 0.6170 0.4867 0.1674 0.103 Uiso 1 1 calc R . .
C17 C 0.46988(16) 0.3570(2) 0.17288(12) 0.1153(12) Uani 1 1 d G . .
H17 H 0.3857 0.4011 0.1656 0.138 Uiso 1 1 calc R . .
C18 C 0.4571(2) 0.2397(2) 0.18263(12) 0.1141(9) Uani 1 1 d G . .
H18 H 0.3644 0.2054 0.1819 0.137 Uiso 1 1 calc R . .
C19 C 0.5829(3) 0.17379(14) 0.19347(11) 0.1068(8) Uani 1 1 d G . .
H19 H 0.5744 0.0953 0.2000 0.128 Uiso 1 1 calc R . .
C20 C 0.7215(2) 0.22509(14) 0.19455(9) 0.0889(8) Uani 1 1 d G . .
H20 H 0.8057 0.1810 0.2018 0.107 Uiso 1 1 calc R . .
C5 C 1.0601(2) 0.5038(2) 0.13009(11) 0.0661(5) Uani 1 1 d . . .
H5A H 1.1300 0.4476 0.1478 0.079 Uiso 1 1 calc R . .
H5B H 1.0579 0.5673 0.1635 0.079 Uiso 1 1 calc R . .
C12 C 1.2125(2) -0.00601(15) 0.09774(11) 0.0560(4) Uani 1 1 d . . .
N1 N 1.1447(3) 0.04628(17) 0.14881(11) 0.0756(5) Uani 1 1 d . . .
C9 C 1.0881(3) 0.25391(17) 0.00828(13) 0.0676(5) Uani 1 1 d . . .
H9A H 1.1039 0.2405 -0.0426 0.081 Uiso 1 1 calc R . .
H9B H 0.9836 0.2680 0.0159 0.081 Uiso 1 1 calc R . .
C6 C 1.2599(2) 0.68153(16) -0.09855(12) 0.0602(5) Uani 1 1 d . . .
C13 C 1.2821(3) -0.1196(2) 0.11098(14) 0.0795(7) Uani 1 1 d . . .
H13A H 1.2655 -0.1419 0.1599 0.119 Uiso 1 1 calc R . .
H13B H 1.3865 -0.1147 0.1021 0.119 Uiso 1 1 calc R . .
H13C H 1.2392 -0.1753 0.0794 0.119 Uiso 1 1 calc R . .
C8 C 1.3561(3) 0.6798(3) -0.16450(15) 0.0912(8) Uani 1 1 d . . .
H8A H 1.4144 0.7483 -0.1662 0.137 Uiso 1 1 calc R . .
H8B H 1.2950 0.6755 -0.2066 0.137 Uiso 1 1 calc R . .
H8C H 1.4203 0.6146 -0.1628 0.137 Uiso 1 1 calc R . .
C7 C 1.1591(3) 0.7821(2) -0.09566(19) 0.0901(8) Uani 1 1 d . . .
H7A H 1.2164 0.8511 -0.0978 0.135 Uiso 1 1 calc R . .
H7B H 1.1039 0.7805 -0.0517 0.135 Uiso 1 1 calc R . .
H7C H 1.0922 0.7797 -0.1357 0.135 Uiso 1 1 calc R . .
C14 C 0.8830(3) 0.3940(3) 0.18851(12) 0.0889(8) Uani 1 1 d . . .
H14A H 0.8875 0.4460 0.2290 0.107 Uiso 1 1 calc R . .
H14B H 0.9559 0.3345 0.1961 0.107 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O5 C5 1.419(3) . ?
O5 C14 1.423(3) . ?
O3 C2 1.414(2) . ?
O3 C6 1.422(2) . ?
C10 C11 1.327(3) . ?
C10 O6 1.336(3) . ?
C10 C9 1.476(3) . ?
O4 C9 1.398(2) . ?
O4 C3 1.419(2) . ?
C3 C2 1.506(3) . ?
C3 C4 1.528(3) . ?
C3 H3 0.9800 . ?
O1 C1 1.399(3) . ?
O1 C4 1.435(2) . ?
O6 N1 1.417(2) . ?
C11 C12 1.411(3) . ?
C11 H11 0.9300 . ?
C2 C1 1.519(3) . ?
C2 H2 0.9800 . ?
O2 C1 1.393(2) . ?
O2 C6 1.420(3) . ?
C1 H1 0.9800 . ?
C4 C5 1.506(3) . ?
C4 H4 0.9800 . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C15 C14 1.477(3) . ?
C16 C17 1.3900 . ?
C16 H16 0.9300 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 C19 1.3900 . ?
C18 H18 0.9300 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C12 N1 1.287(3) . ?
C12 C13 1.493(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C6 C7 1.491(3) . ?
C6 C8 1.505(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 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
C5 O5 C14 109.72(17) . . ?
C2 O3 C6 109.08(15) . . ?
C11 C10 O6 109.78(17) . . ?
C11 C10 C9 134.0(2) . . ?
O6 C10 C9 116.20(19) . . ?
C9 O4 C3 112.96(14) . . ?
O4 C3 C2 110.30(15) . . ?
O4 C3 C4 110.15(16) . . ?
C2 C3 C4 101.74(15) . . ?
O4 C3 H3 111.4 . . ?
C2 C3 H3 111.4 . . ?
C4 C3 H3 111.4 . . ?
C1 O1 C4 110.08(14) . . ?
C10 O6 N1 107.98(15) . . ?
C10 C11 C12 105.42(17) . . ?
C10 C11 H11 127.3 . . ?
C12 C11 H11 127.3 . . ?
O3 C2 C3 108.45(15) . . ?
O3 C2 C1 103.66(14) . . ?
C3 C2 C1 104.82(16) . . ?
O3 C2 H2 113.1 . . ?
C3 C2 H2 113.1 . . ?
C1 C2 H2 113.1 . . ?
C1 O2 C6 110.81(14) . . ?
O2 C1 O1 112.54(16) . . ?
O2 C1 C2 105.23(16) . . ?
O1 C1 C2 107.23(15) . . ?
O2 C1 H1 110.6 . . ?
O1 C1 H1 110.6 . . ?
C2 C1 H1 110.6 . . ?
O1 C4 C5 106.44(16) . . ?
O1 C4 C3 104.59(15) . . ?
C5 C4 C3 115.66(17) . . ?
O1 C4 H4 110.0 . . ?
C5 C4 H4 110.0 . . ?
C3 C4 H4 110.0 . . ?
C16 C15 C20 120.0 . . ?
C16 C15 C14 121.66(18) . . ?
C20 C15 C14 118.32(18) . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
O5 C5 C4 108.39(16) . . ?
O5 C5 H5A 110.0 . . ?
C4 C5 H5A 110.0 . . ?
O5 C5 H5B 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
N1 C12 C11 111.03(17) . . ?
N1 C12 C13 120.23(19) . . ?
C11 C12 C13 128.74(19) . . ?
C12 N1 O6 105.78(16) . . ?
O4 C9 C10 109.17(16) . . ?
O4 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
O4 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
O2 C6 O3 105.82(15) . . ?
O2 C6 C7 110.2(2) . . ?
O3 C6 C7 108.09(18) . . ?
O2 C6 C8 109.28(19) . . ?
O3 C6 C8 110.01(19) . . ?
C7 C6 C8 113.2(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O5 C14 C15 111.29(19) . . ?
O5 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
O5 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.050

