# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_corn

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H26 N2 O5'
_chemical_formula_sum            'C25 H26 N2 O5'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         434.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 unk

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                   8.2328(2)
_cell_length_b                   12.2627(2)
_cell_length_c                   21.8139(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2202.25(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4605
_cell_measurement_theta_min      3.6014
_cell_measurement_theta_max      72.2011
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_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. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8398
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.05
_diffrn_reflns_theta_max         72.34
_reflns_number_total             4239
_reflns_number_gt                4009
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0538P)²+0.0362P] 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     SHELXL
_refine_ls_extinction_coef       0.0038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(15)
_refine_ls_number_reflns         4239
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_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
O1 O 0.22880(12) 0.36440(8) 0.13636(4) 0.0258(2) Uani 1 1 d . . .
O2 O 0.23677(16) 0.52904(9) 0.08958(5) 0.0352(3) Uani 1 1 d . . .
O3 O -0.10372(16) 0.46954(8) 0.18404(5) 0.0336(3) Uani 1 1 d . . .
O4 O -0.25671(14) 0.15061(9) 0.14417(5) 0.0336(3) Uani 1 1 d . . .
O5 O -0.15352(14) 0.12286(8) 0.23738(5) 0.0297(2) Uani 1 1 d . . .
N1 N 0.08136(16) 0.39008(10) 0.05166(5) 0.0264(3) Uani 1 1 d . . .
N2 N -0.14933(15) 0.29293(9) 0.20292(5) 0.0215(3) Uani 1 1 d . . .
C1 C 0.33356(18) 0.35838(13) 0.29213(7) 0.0282(3) Uani 1 1 d . . .
H1A H 0.3037 0.4316 0.3009 0.034 Uiso 1 1 calc R . .
C2 C 0.3513(2) 0.28404(15) 0.33969(8) 0.0359(4) Uani 1 1 d . . .
H2A H 0.3331 0.3063 0.3808 0.043 Uiso 1 1 calc R . .
C3 C 0.3954(2) 0.17773(15) 0.32717(8) 0.0383(4) Uani 1 1 d . . .
H3A H 0.4085 0.1270 0.3597 0.046 Uiso 1 1 calc R . .
C4 C 0.4207(2) 0.14494(14) 0.26706(8) 0.0351(4) Uani 1 1 d . . .
H4A H 0.4505 0.0717 0.2585 0.042 Uiso 1 1 calc R . .
C5 C 0.40279(19) 0.21853(13) 0.21972(7) 0.0295(3) Uani 1 1 d . . .
H5A H 0.4202 0.1956 0.1786 0.035 Uiso 1 1 calc R . .
C6 C 0.35931(17) 0.32629(12) 0.23176(7) 0.0242(3) Uani 1 1 d . . .
C7 C 0.3430(2) 0.40745(12) 0.18073(7) 0.0281(3) Uani 1 1 d . . .
H7A H 0.3033 0.4779 0.1970 0.034 Uiso 1 1 calc R . .
H7B H 0.4499 0.4198 0.1611 0.034 Uiso 1 1 calc R . .
C8 C 0.18421(19) 0.43684(12) 0.09245(7) 0.0249(3) Uani 1 1 d . . .
C9 C -0.03077(18) 0.30005(12) 0.06596(6) 0.0247(3) Uani 1 1 d . . .
H9A H 0.0164 0.2408 0.0919 0.030 Uiso 1 1 calc R . .
C10 C -0.0819(2) 0.26465(15) 0.00129(7) 0.0351(4) Uani 1 1 d . . .
H10A H -0.1921 0.2323 0.0014 0.042 Uiso 1 1 calc R . .
H10B H -0.0044 0.2112 -0.0161 0.042 Uiso 1 1 calc R . .
C11 C -0.0787(2) 0.37335(16) -0.03511(7) 0.0424(4) Uani 1 1 d . . .
H11A H 0.0035 0.3713 -0.0682 0.051 Uiso 1 1 calc R . .
H11B H -0.1864 0.3899 -0.0530 0.051 Uiso 1 1 calc R . .
C12 C -0.0328(2) 0.45631(15) 0.01451(7) 0.0333(4) Uani 1 1 d . . .
H12A H 0.0137 0.5261 -0.0015 0.040 Uiso 1 1 calc R . .
C13 C -0.1773(2) 0.47052(14) 0.05867(7) 0.0347(4) Uani 1 1 d . . .
H13A H -0.2803 0.4797 0.0359 0.042 Uiso 1 1 calc R . .
H13B H -0.1611 0.5341 0.0859 0.042 Uiso 1 1 calc R . .
C14 C -0.17670(18) 0.36262(13) 0.09556(6) 0.0253(3) Uani 1 1 d . . .
H14A H -0.2807 0.3218 0.0897 0.030 Uiso 1 1 calc R . .
C15 C -0.14300(18) 0.38205(11) 0.16318(7) 0.0235(3) Uani 1 1 d . . .
C16 C -0.19302(17) 0.18601(12) 0.18958(7) 0.0249(3) Uani 1 1 d . . .
C17 C -0.0576(2) 0.18442(12) 0.28143(7) 0.0285(3) Uani 1 1 d . . .
H17A H 0.0594 0.1676 0.2769 0.034 Uiso 1 1 calc R . .
H17B H -0.0916 0.1673 0.3239 0.034 Uiso 1 1 calc R . .
C18 C -0.09126(17) 0.30380(11) 0.26624(6) 0.0206(3) Uani 1 1 d . . .
H18A H 0.0126 0.3460 0.2669 0.025 Uiso 1 1 calc R . .
C19 C -0.21584(17) 0.35839(13) 0.30835(6) 0.0251(3) Uani 1 1 d . . .
H19A H -0.2448 0.4311 0.2919 0.030 Uiso 1 1 calc R . .
H19B H -0.3158 0.3137 0.3101 0.030 Uiso 1 1 calc R . .
C20 C -0.14527(17) 0.37021(12) 0.37185(6) 0.0230(3) Uani 1 1 d . . .
C21 C -0.1849(2) 0.29780(13) 0.41817(7) 0.0355(4) Uani 1 1 d . . .
H21A H -0.2656 0.2438 0.4112 0.043 Uiso 1 1 calc R . .
C22 C -0.1079(3) 0.30328(15) 0.47459(8) 0.0450(5) Uani 1 1 d . . .
H22A H -0.1361 0.2531 0.5060 0.054 Uiso 1 1 calc R . .
C23 C 0.0100(2) 0.38157(15) 0.48542(7) 0.0402(4) Uani 1 1 d . . .
H23A H 0.0640 0.3844 0.5239 0.048 Uiso 1 1 calc R . .
C24 C 0.0483(2) 0.45517(14) 0.44003(8) 0.0364(4) Uani 1 1 d . . .
H24A H 0.1276 0.5099 0.4474 0.044 Uiso 1 1 calc R . .
C25 C -0.0289(2) 0.44970(12) 0.38341(7) 0.0286(3) Uani 1 1 d . . .
H25A H -0.0018 0.5008 0.3523 0.034 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
O1 C8 1.3570(17) . ?
O1 C7 1.4491(17) . ?
O2 C8 1.2122(18) . ?
O3 C15 1.2094(18) . ?
O4 C16 1.2020(18) . ?
O5 C16 1.3390(18) . ?
O5 C17 1.4548(18) . ?
N1 C8 1.356(2) . ?
N1 C9 1.4725(19) . ?
N1 C12 1.4829(19) . ?
N2 C16 1.3903(18) . ?
N2 C15 1.3959(18) . ?
N2 C18 1.4677(17) . ?
C1 C2 1.389(2) . ?
C1 C6 1.391(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.381(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.379(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.394(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.499(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C10 1.535(2) . ?
C9 C14 1.5650(19) . ?
C9 H9A 1.0000 . ?
C10 C11 1.552(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.533(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.541(2) . ?
C12 H12A 1.0000 . ?
C13 C14 1.549(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.520(2) . ?
C14 H14A 1.0000 . ?
C17 C18 1.526(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5310(19) . ?
C18 H18A 1.0000 . ?
C19 C20 1.5089(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.384(2) . ?
C20 C25 1.390(2) . ?
C21 C22 1.386(2) . ?
C21 H21A 0.9500 . ?
C22 C23 1.385(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.376(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.390(2) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?

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
C8 O1 C7 114.11(11) . . ?
C16 O5 C17 110.24(11) . . ?
C8 N1 C9 124.73(12) . . ?
C8 N1 C12 121.51(13) . . ?
C9 N1 C12 97.42(12) . . ?
C16 N2 C15 128.16(12) . . ?
C16 N2 C18 111.53(11) . . ?
C15 N2 C18 120.08(11) . . ?
C2 C1 C6 120.38(15) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C1 C2 C3 119.98(16) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 120.02(16) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 120.12(16) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 120.45(15) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C1 C6 C5 119.06(14) . . ?
C1 C6 C7 120.10(14) . . ?
C5 C6 C7 120.83(14) . . ?
O1 C7 C6 108.18(12) . . ?
O1 C7 H7A 110.1 . . ?
C6 C7 H7A 110.1 . . ?
O1 C7 H7B 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
O2 C8 O1 123.41(14) . . ?
O2 C8 N1 125.70(14) . . ?
O1 C8 N1 110.81(13) . . ?
N1 C9 C10 100.91(12) . . ?
N1 C9 C14 101.60(11) . . ?
C10 C9 C14 107.89(12) . . ?
N1 C9 H9A 114.9 . . ?
C10 C9 H9A 114.9 . . ?
C14 C9 H9A 114.9 . . ?
C9 C10 C11 102.87(13) . . ?
C9 C10 H10A 111.2 . . ?
C11 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
C11 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
C12 C11 C10 102.30(12) . . ?
C12 C11 H11A 111.3 . . ?
C10 C11 H11A 111.3 . . ?
C12 C11 H11B 111.3 . . ?
C10 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
N1 C12 C11 100.29(13) . . ?
N1 C12 C13 102.10(11) . . ?
C11 C12 C13 109.03(15) . . ?
N1 C12 H12A 114.6 . . ?
C11 C12 H12A 114.6 . . ?
C13 C12 H12A 114.6 . . ?
C12 C13 C14 103.06(13) . . ?
C12 C13 H13A 111.2 . . ?
C14 C13 H13A 111.2 . . ?
C12 C13 H13B 111.2 . . ?
C14 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
C15 C14 C13 111.78(13) . . ?
C15 C14 C9 109.71(12) . . ?
C13 C14 C9 101.94(12) . . ?
C15 C14 H14A 111.0 . . ?
C13 C14 H14A 111.0 . . ?
C9 C14 H14A 111.0 . . ?
O3 C15 N2 118.08(13) . . ?
O3 C15 C14 123.58(13) . . ?
N2 C15 C14 118.24(12) . . ?
O4 C16 O5 122.60(14) . . ?
O4 C16 N2 128.76(14) . . ?
O5 C16 N2 108.64(12) . . ?
O5 C17 C18 104.83(11) . . ?
O5 C17 H17A 110.8 . . ?
C18 C17 H17A 110.8 . . ?
O5 C17 H17B 110.8 . . ?
C18 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
N2 C18 C17 100.15(10) . . ?
N2 C18 C19 112.71(11) . . ?
C17 C18 C19 114.25(12) . . ?
N2 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
C20 C19 C18 109.56(11) . . ?
C20 C19 H19A 109.8 . . ?
C18 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
C18 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C21 C20 C25 118.68(14) . . ?
C21 C20 C19 121.18(14) . . ?
C25 C20 C19 119.95(13) . . ?
C20 C21 C22 120.62(16) . . ?
C20 C21 H21A 119.7 . . ?
C22 C21 H21A 119.7 . . ?
C23 C22 C21 120.35(16) . . ?
C23 C22 H22A 119.8 . . ?
C21 C22 H22A 119.8 . . ?
C24 C23 C22 119.48(15) . . ?
C24 C23 H23A 120.3 . . ?
C22 C23 H23A 120.3 . . ?
C23 C24 C25 120.18(16) . . ?
C23 C24 H24A 119.9 . . ?
C25 C24 H24A 119.9 . . ?
C20 C25 C24 120.66(15) . . ?
C20 C25 H25A 119.7 . . ?
C24 C25 H25A 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        72.34
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.031

_database_code_depnum_ccdc_archive 'CCDC 954104'
