# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_cd212389

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H38 N2 O4'
_chemical_formula_weight         514.64

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   8.4087(9)
_cell_length_b                   17.6504(18)
_cell_length_c                   19.4816(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.184(2)
_cell_angle_gamma                90.00
_cell_volume                     2874.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2611
_cell_measurement_theta_min      5.072
_cell_measurement_theta_max      51.776

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.156
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.81021
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8562
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2818
_reflns_number_gt                2212
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0625P)^2^+1.2405P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         2818
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1217
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
N1 N 0.67507(16) 0.11845(7) 0.41246(6) 0.0460(3) Uani 1 1 d . . .
O1 O 0.30007(17) 0.21978(9) 0.28447(6) 0.0738(4) Uani 1 1 d . . .
O2 O 0.22902(14) 0.26360(8) 0.38322(6) 0.0597(4) Uani 1 1 d . . .
C1 C 0.5712(2) 0.14822(9) 0.36118(8) 0.0470(4) Uani 1 1 d . . .
H1 H 0.5841 0.1465 0.3144 0.056 Uiso 1 1 calc R . .
C2 C 0.44558(18) 0.18086(9) 0.38853(7) 0.0422(4) Uani 1 1 d . . .
C3 C 0.47356(18) 0.17091(9) 0.46085(7) 0.0438(4) Uani 1 1 d . . .
H3 H 0.4079 0.1878 0.4932 0.053 Uiso 1 1 calc R . .
C4 C 0.61337(19) 0.13224(8) 0.47495(7) 0.0420(4) Uani 1 1 d . . .
C5 C 0.68757(18) 0.11088(9) 0.54529(7) 0.0410(4) Uani 1 1 d . . .
C6 C 0.7747(2) 0.16389(9) 0.58591(8) 0.0482(4) Uani 1 1 d . . .
H6 H 0.7965 0.2108 0.5673 0.058 Uiso 1 1 calc R . .
C7 C 0.8298(2) 0.14811(11) 0.65393(8) 0.0551(4) Uani 1 1 d . . .
H7 H 0.8881 0.1844 0.6806 0.066 Uiso 1 1 calc R . .
C8 C 0.7988(2) 0.07938(11) 0.68209(8) 0.0546(4) Uani 1 1 d . . .
H8 H 0.8355 0.0689 0.7279 0.066 Uiso 1 1 calc R . .
C9 C 0.7130(2) 0.02582(10) 0.64236(9) 0.0576(5) Uani 1 1 d . . .
H9 H 0.6922 -0.0211 0.6612 0.069 Uiso 1 1 calc R . .
C10 C 0.6577(2) 0.04158(10) 0.57466(8) 0.0517(4) Uani 1 1 d . . .
H10 H 0.5994 0.0051 0.5483 0.062 Uiso 1 1 calc R . .
C11 C 0.8282(2) 0.08039(11) 0.40077(8) 0.0557(5) Uani 1 1 d . . .
C12 C 0.9664(2) 0.12213(15) 0.44099(12) 0.0817(7) Uani 1 1 d . . .
H12A H 0.9612 0.1749 0.4291 0.123 Uiso 1 1 calc R . .
H12B H 1.0659 0.1014 0.4297 0.123 Uiso 1 1 calc R . .
H12C H 0.9594 0.1165 0.4896 0.123 Uiso 1 1 calc R . .
C13 C 0.8223(3) -0.00141(13) 0.42276(14) 0.0913(8) Uani 1 1 d . . .
H13A H 0.8149 -0.0039 0.4715 0.137 Uiso 1 1 calc R . .
H13B H 0.9178 -0.0268 0.4123 0.137 Uiso 1 1 calc R . .
H13C H 0.7307 -0.0255 0.3984 0.137 Uiso 1 1 calc R . .
C14 C 0.8523(3) 0.08389(17) 0.32465(11) 0.1002(9) Uani 1 1 d . . .
H14A H 0.7673 0.0570 0.2982 0.150 Uiso 1 1 calc R . .
H14B H 0.9530 0.0611 0.3177 0.150 Uiso 1 1 calc R . .
H14C H 0.8517 0.1358 0.3099 0.150 Uiso 1 1 calc R . .
C15 C 0.31984(19) 0.22135(9) 0.34646(8) 0.0456(4) Uani 1 1 d . . .
C16 C 0.1065(3) 0.30693(13) 0.34326(10) 0.0743(6) Uani 1 1 d . . .
H16A H 0.1542 0.3373 0.3101 0.111 Uiso 1 1 calc R . .
H16B H 0.0540 0.3392 0.3734 0.111 Uiso 1 1 calc R . .
H16C H 0.0297 0.2731 0.3196 0.111 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0542(8) 0.0488(8) 0.0348(7) 0.0008(6) 0.0041(6) 0.0080(6)
O1 0.0835(10) 0.0995(11) 0.0360(7) -0.0036(6) -0.0048(6) 0.0311(8)
O2 0.0586(7) 0.0792(9) 0.0414(6) 0.0047(6) 0.0055(5) 0.0199(6)
C1 0.0598(10) 0.0488(9) 0.0316(7) -0.0011(6) 0.0014(7) 0.0047(8)
C2 0.0475(8) 0.0423(8) 0.0360(8) -0.0014(6) 0.0007(6) -0.0027(7)
C3 0.0473(8) 0.0487(9) 0.0356(8) -0.0003(6) 0.0054(6) -0.0005(7)
C4 0.0499(9) 0.0413(8) 0.0345(8) -0.0001(6) 0.0031(6) -0.0026(7)
C5 0.0438(8) 0.0441(8) 0.0352(8) 0.0008(6) 0.0043(6) 0.0004(7)
C6 0.0579(10) 0.0452(9) 0.0413(8) 0.0016(7) 0.0044(7) -0.0053(7)
C7 0.0617(10) 0.0585(10) 0.0432(9) -0.0050(8) -0.0030(8) -0.0076(8)
C8 0.0614(11) 0.0665(11) 0.0348(8) 0.0070(8) -0.0005(7) 0.0017(9)
C9 0.0695(11) 0.0538(10) 0.0484(10) 0.0135(8) 0.0012(8) -0.0071(9)
C10 0.0610(10) 0.0480(9) 0.0442(9) 0.0024(7) -0.0023(7) -0.0093(8)
C11 0.0626(11) 0.0609(11) 0.0443(9) 0.0021(8) 0.0094(8) 0.0201(9)
C12 0.0571(12) 0.1032(18) 0.0869(15) -0.0052(13) 0.0166(11) 0.0101(11)
C13 0.1022(18) 0.0620(13) 0.1133(19) 0.0067(13) 0.0289(15) 0.0286(13)
C14 0.1075(19) 0.144(2) 0.0528(12) 0.0067(13) 0.0234(12) 0.0666(18)
C15 0.0491(9) 0.0506(9) 0.0366(8) -0.0007(7) 0.0021(7) -0.0012(7)
C16 0.0705(13) 0.0926(15) 0.0602(12) 0.0131(11) 0.0089(10) 0.0321(12)

_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
N1 C1 1.3597(19) . ?
N1 C4 1.3952(19) . ?
N1 C11 1.492(2) . ?
O1 C15 1.2014(18) . ?
O2 C15 1.330(2) . ?
O2 C16 1.442(2) . ?
C1 C2 1.361(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.414(2) . ?
C2 C15 1.454(2) . ?
C3 C4 1.362(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.492(2) . ?
C5 C6 1.383(2) . ?
C5 C10 1.385(2) . ?
C6 C7 1.384(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C13 1.508(3) . ?
C11 C14 1.519(3) . ?
C11 C12 1.520(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C1 N1 C4 107.70(13) . . ?
C1 N1 C11 123.96(13) . . ?
C4 N1 C11 128.32(13) . . ?
C15 O2 C16 115.14(13) . . ?
N1 C1 C2 109.88(13) . . ?
N1 C1 H1 125.1 . . ?
C2 C1 H1 125.1 . . ?
C1 C2 C3 106.53(13) . . ?
C1 C2 C15 122.37(14) . . ?
C3 C2 C15 130.96(14) . . ?
C4 C3 C2 108.10(13) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
C3 C4 N1 107.79(13) . . ?
C3 C4 C5 125.36(14) . . ?
N1 C4 C5 126.83(14) . . ?
C6 C5 C10 118.00(14) . . ?
C6 C5 C4 119.87(13) . . ?
C10 C5 C4 121.76(14) . . ?
C5 C6 C7 120.91(15) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 120.24(16) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.65(15) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 120.12(16) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 121.07(15) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
N1 C11 C13 109.42(16) . . ?
N1 C11 C14 109.79(14) . . ?
C13 C11 C14 109.15(18) . . ?
N1 C11 C12 109.12(14) . . ?
C13 C11 C12 111.35(18) . . ?
C14 C11 C12 107.98(19) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 O2 121.92(15) . . ?
O1 C15 C2 124.66(15) . . ?
O2 C15 C2 113.38(13) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C4 N1 C1 C2 0.25(18) . . . . ?
C11 N1 C1 C2 -178.20(15) . . . . ?
N1 C1 C2 C3 0.19(18) . . . . ?
N1 C1 C2 C15 176.28(14) . . . . ?
C1 C2 C3 C4 -0.57(18) . . . . ?
C15 C2 C3 C4 -176.19(16) . . . . ?
C2 C3 C4 N1 0.72(17) . . . . ?
C2 C3 C4 C5 179.17(14) . . . . ?
C1 N1 C4 C3 -0.61(17) . . . . ?
C11 N1 C4 C3 177.75(15) . . . . ?
C1 N1 C4 C5 -179.03(15) . . . . ?
C11 N1 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 -80.3(2) . . . . ?
N1 C4 C5 C6 97.87(19) . . . . ?
C3 C4 C5 C10 92.5(2) . . . . ?
N1 C4 C5 C10 -89.3(2) . . . . ?
C10 C5 C6 C7 -0.2(2) . . . . ?
C4 C5 C6 C7 172.88(15) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 C9 C10 C5 0.3(3) . . . . ?
C6 C5 C10 C9 0.0(3) . . . . ?
C4 C5 C10 C9 -172.89(16) . . . . ?
C1 N1 C11 C13 -116.97(19) . . . . ?
C4 N1 C11 C13 64.9(2) . . . . ?
C1 N1 C11 C14 2.8(3) . . . . ?
C4 N1 C11 C14 -175.32(19) . . . . ?
C1 N1 C11 C12 120.97(18) . . . . ?
C4 N1 C11 C12 -57.2(2) . . . . ?
C16 O2 C15 O1 -0.1(3) . . . . ?
C16 O2 C15 C2 177.79(16) . . . . ?
C1 C2 C15 O1 12.4(3) . . . . ?
C3 C2 C15 O1 -172.53(17) . . . . ?
C1 C2 C15 O2 -165.36(15) . . . . ?
C3 C2 C15 O2 9.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 955843'