# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

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#                 Cambridge Crystallographic Data Centre
#                                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
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_cu_20140416aa_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N2 O6'
_chemical_formula_weight         384.38
_chemical_absolute_configuration ad

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)   '

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

_cell_length_a                   11.9298(3)
_cell_length_b                   5.8381(2)
_cell_length_c                   13.6572(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.667(2)
_cell_angle_gamma                90.00
_cell_volume                     948.03(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1886
_cell_measurement_theta_min      7.45
_cell_measurement_theta_max      65.94

_exptl_crystal_description       block
_exptl_crystal_colour            'light gray'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8050
_exptl_absorpt_correction_T_max  0.8915
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4372
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         7.45
_diffrn_reflns_theta_max         65.00
_reflns_number_total             2492
_reflns_number_gt                2282
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0956P)²+0.3837P] 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   0.0(4)
_refine_ls_number_reflns         2492
_refine_ls_number_parameters     233
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1772
_refine_ls_wR_factor_gt          0.1697
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
C1 C 1.3581(4) 0.0615(11) 0.4323(3) 0.0769(14) Uani 1 1 d . . .
C2 C 1.3161(4) -0.1458(11) 0.4056(4) 0.0810(14) Uani 1 1 d . . .
H2 H 1.3459 -0.2293 0.3559 0.097 Uiso 1 1 calc R . .
C3 C 1.2280(4) -0.2310(10) 0.4539(3) 0.0700(11) Uani 1 1 d . . .
H3 H 1.1966 -0.3718 0.4354 0.084 Uiso 1 1 calc R . .
C4 C 1.1859(3) -0.1093(8) 0.5297(3) 0.0586(9) Uani 1 1 d . . .
C5 C 1.2305(4) 0.1029(9) 0.5548(3) 0.0717(11) Uani 1 1 d . . .
H5 H 1.2016 0.1875 0.6047 0.086 Uiso 1 1 calc R . .
C6 C 1.3184(4) 0.1897(10) 0.5055(4) 0.0792(13) Uani 1 1 d . . .
H6 H 1.3495 0.3320 0.5220 0.095 Uiso 1 1 calc R . .
C7 C 1.0916(3) -0.2136(8) 0.5803(3) 0.0552(9) Uani 1 1 d . . .
C8 C 1.0500(3) -0.0913(7) 0.6675(3) 0.0583(9) Uani 1 1 d . . .
H8A H 1.0235 0.0596 0.6468 0.070 Uiso 1 1 calc R . .
H8B H 1.1127 -0.0706 0.7166 0.070 Uiso 1 1 calc R . .
C9 C 0.9560(3) -0.2151(7) 0.7146(3) 0.0567(9) Uani 1 1 d . . .
H9 H 0.8954 -0.2473 0.6636 0.068 Uiso 1 1 calc R . .
C10 C 0.9901(4) -0.4381(8) 0.7660(3) 0.0669(10) Uani 1 1 d . . .
H10A H 1.0291 -0.5339 0.7217 0.080 Uiso 1 1 calc R . .
H10B H 0.9231 -0.5191 0.7823 0.080 Uiso 1 1 calc R . .
C11 C 1.0657(4) -0.3969(8) 0.8589(3) 0.0672(10) Uani 1 1 d . . .
H11A H 1.0762 -0.5393 0.8951 0.081 Uiso 1 1 calc R . .
H11B H 1.1388 -0.3446 0.8419 0.081 Uiso 1 1 calc R . .
C12 C 1.0149(3) -0.2209(9) 0.9222(3) 0.0627(9) Uani 1 1 d . . .
H12A H 0.9462 -0.2810 0.9455 0.075 Uiso 1 1 calc R . .
H12B H 1.0668 -0.1881 0.9789 0.075 Uiso 1 1 calc R . .
O6 O 0.99043(15) -0.0120(4) 0.86762(14) 0.040 Uani 1 1 d . . .
C13 C 0.8020(3) -0.0317(8) 0.7975(3) 0.0582(9) Uani 1 1 d . A .
C15 C 0.6719(2) 0.1867(7) 0.8745(3) 0.117(10) Uani 0.55(2) 1 d P A 1
H15A H 0.6147 0.0718 0.8583 0.141 Uiso 0.55(2) 1 calc PR A 1
H15B H 0.6645 0.3074 0.8256 0.141 Uiso 0.55(2) 1 calc PR A 1
C14 C 0.6610(2) 0.2839(7) 0.9778(3) 0.0642(11) Uani 1 1 d R . .
C17 C 0.6073(2) 0.1918(7) 1.0553(3) 0.0863(16) Uani 1 1 d R A .
H17 H 0.5751 0.0467 1.0505 0.104 Uiso 1 1 calc R . .
C18 C 0.6027(6) 0.321(2) 1.1402(5) 0.128 Uani 1 1 d . . .
H18 H 0.5660 0.2646 1.1927 0.154 Uiso 1 1 calc R A .
C19 C 0.6518(7) 0.531(3) 1.1465(7) 0.177 Uani 1 1 d . A .
H19 H 0.6487 0.6179 1.2033 0.213 Uiso 1 1 calc R . .
C20 C 0.7048(6) 0.6143(15) 1.0713(10) 0.160(5) Uani 1 1 d . . .
H20 H 0.7402 0.7561 1.0766 0.192 Uiso 1 1 calc R A .
C16 C 0.7064(4) 0.4910(12) 0.9880(6) 0.0963(18) Uani 1 1 d . A .
H16 H 0.7408 0.5537 0.9355 0.116 Uiso 1 1 calc R . .
C15' C 0.6631(8) 0.113(3) 0.8975(10) 0.061(4) Uani 0.45(2) 1 d P A 2
H15C H 0.6199 0.1670 0.8388 0.073 Uiso 0.45(2) 1 calc PR A 2
H15D H 0.6318 -0.0317 0.9172 0.073 Uiso 0.45(2) 1 calc PR A 2
N1 N 1.4543(4) 0.1529(13) 0.3821(4) 0.1009(19) Uani 1 1 d . . .
N2 N 0.9130(3) -0.0588(7) 0.7867(2) 0.064 Uani 1 1 d . . .
O1 O 1.4869(4) 0.3423(13) 0.4005(4) 0.127(2) Uani 1 1 d . . .
O2 O 1.4932(5) 0.0251(14) 0.3227(5) 0.151(3) Uani 1 1 d . . .
O3 O 1.0509(3) -0.3949(6) 0.5514(2) 0.0735(8) Uani 1 1 d . . .
O4 O 0.7302(2) -0.0968(9) 0.7375(2) 0.0882(12) Uani 1 1 d . . .
O5 O 0.7845(2) 0.0850(7) 0.87892(19) 0.0693(8) Uani 1 1 d . . .


_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 C2 1.349(9) . ?
C1 C6 1.365(7) . ?
C1 N1 1.482(6) . ?
C2 C3 1.378(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(7) . ?
C4 C7 1.497(6) . ?
C5 C6 1.387(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O3 1.217(6) . ?
C7 C8 1.506(5) . ?
C8 C9 1.521(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.466(5) . ?
C9 C10 1.518(6) . ?
C9 H9 0.9800 . ?
C10 C11 1.516(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.501(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O6 1.447(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O6 N2 1.408(4) . ?
C13 O4 1.198(5) . ?
C13 O5 1.335(5) . ?
C13 N2 1.354(5) . ?
C15 O5 1.466(4) . ?
C15 C14 1.5358 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 C16 1.328(8) . ?
C14 C17 1.3900 . ?
C14 C15' 1.484(14) . ?
C17 C18 1.390(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.357(17) . ?
C18 H18 0.9300 . ?
C19 C20 1.339(16) . ?
C19 H19 0.9300 . ?
C20 C16 1.348(11) . ?
C20 H20 0.9300 . ?
C16 H16 0.9300 . ?
C15' O5 1.500(10) . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?
N1 O1 1.192(9) . ?
N1 O2 1.222(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
C2 C1 C6 123.1(5) . . ?
C2 C1 N1 118.9(6) . . ?
C6 C1 N1 118.0(6) . . ?
C1 C2 C3 118.4(5) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 120.7(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 C7 122.6(4) . . ?
C3 C4 C7 117.9(4) . . ?
C4 C5 C6 119.9(5) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 118.5(5) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O3 C7 C4 120.0(4) . . ?
O3 C7 C8 121.3(4) . . ?
C4 C7 C8 118.7(4) . . ?
C7 C8 C9 114.2(3) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N2 C9 C10 108.5(3) . . ?
N2 C9 C8 107.4(3) . . ?
C10 C9 C8 115.1(3) . . ?
N2 C9 H9 108.6 . . ?
C10 C9 H9 108.6 . . ?
C8 C9 H9 108.6 . . ?
C9 C10 C11 111.7(4) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 110.5(3) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
O6 C12 C11 110.8(3) . . ?
O6 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
O6 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N2 O6 C12 109.4(3) . . ?
O4 C13 O5 125.5(4) . . ?
O4 C13 N2 122.7(4) . . ?
O5 C13 N2 111.7(3) . . ?
O5 C15 C14 104.90(17) . . ?
O5 C15 H15A 110.8 . . ?
C14 C15 H15A 110.8 . . ?
O5 C15 H15B 110.8 . . ?
C14 C15 H15B 110.8 . . ?
H15A C15 H15B 108.8 . . ?
C16 C14 C17 118.8(3) . . ?
C16 C14 C15' 131.2(7) . . ?
C17 C14 C15' 109.8(7) . . ?
C16 C14 C15 111.7(3) . . ?
C17 C14 C15 129.5 . . ?
C15' C14 C15 20.9(7) . . ?
C18 C17 C14 118.5(5) . . ?
C18 C17 H17 120.7 . . ?
C14 C17 H17 120.7 . . ?
C19 C18 C17 119.8(7) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 120.4(7) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C16 119.6(9) . . ?
C19 C20 H20 120.2 . . ?
C16 C20 H20 120.2 . . ?
C14 C16 C20 122.8(7) . . ?
C14 C16 H16 118.6 . . ?
C20 C16 H16 118.6 . . ?
C14 C15' O5 105.8(7) . . ?
C14 C15' H15C 110.6 . . ?
O5 C15' H15C 110.6 . . ?
C14 C15' H15D 110.6 . . ?
O5 C15' H15D 110.6 . . ?
H15C C15' H15D 108.7 . . ?
O1 N1 O2 124.8(6) . . ?
O1 N1 C1 119.2(7) . . ?
O2 N1 C1 115.9(7) . . ?
C13 N2 O6 118.5(3) . . ?
C13 N2 C9 123.0(3) . . ?
O6 N2 C9 113.9(3) . . ?
C13 O5 C15 112.1(3) . . ?
C13 O5 C15' 114.5(5) . . ?
C15 O5 C15' 21.3(7) . . ?

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
C6 C1 C2 C3 0.8(7) . . . . ?
N1 C1 C2 C3 178.9(4) . . . . ?
C1 C2 C3 C4 -1.8(7) . . . . ?
C2 C3 C4 C5 2.1(7) . . . . ?
C2 C3 C4 C7 -178.9(4) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
C7 C4 C5 C6 179.6(4) . . . . ?
C2 C1 C6 C5 -0.1(7) . . . . ?
N1 C1 C6 C5 -178.2(4) . . . . ?
C4 C5 C6 C1 0.4(7) . . . . ?
C5 C4 C7 O3 175.6(4) . . . . ?
C3 C4 C7 O3 -3.4(6) . . . . ?
C5 C4 C7 C8 -5.2(6) . . . . ?
C3 C4 C7 C8 175.8(4) . . . . ?
O3 C7 C8 C9 0.6(6) . . . . ?
C4 C7 C8 C9 -178.7(3) . . . . ?
C7 C8 C9 N2 -170.9(3) . . . . ?
C7 C8 C9 C10 68.1(4) . . . . ?
N2 C9 C10 C11 -50.3(4) . . . . ?
C8 C9 C10 C11 70.0(4) . . . . ?
C9 C10 C11 C12 50.3(5) . . . . ?
C10 C11 C12 O6 -54.9(5) . . . . ?
C11 C12 O6 N2 60.6(4) . . . . ?
O5 C15 C14 C16 84.0(3) . . . . ?
O5 C15 C14 C17 -99.8(2) . . . . ?
O5 C15 C14 C15' -77.9(12) . . . . ?
C16 C14 C17 C18 0.4(4) . . . . ?
C15' C14 C17 C18 176.3(7) . . . . ?
C15 C14 C17 C18 -175.6(4) . . . . ?
C14 C17 C18 C19 -1.1(8) . . . . ?
C17 C18 C19 C20 0.0(11) . . . . ?
C18 C19 C20 C16 1.9(12) . . . . ?
C17 C14 C16 C20 1.5(7) . . . . ?
C15' C14 C16 C20 -173.3(8) . . . . ?
C15 C14 C16 C20 178.2(5) . . . . ?
C19 C20 C16 C14 -2.7(10) . . . . ?
C16 C14 C15' O5 51.1(13) . . . . ?
C17 C14 C15' O5 -124.0(8) . . . . ?
C15 C14 C15' O5 73.7(12) . . . . ?
C2 C1 N1 O1 175.0(5) . . . . ?
C6 C1 N1 O1 -6.9(7) . . . . ?
C2 C1 N1 O2 -4.0(7) . . . . ?
C6 C1 N1 O2 174.2(5) . . . . ?
O4 C13 N2 O6 -169.6(4) . . . . ?
O5 C13 N2 O6 13.7(6) . . . . ?
O4 C13 N2 C9 -15.0(7) . . . . ?
O5 C13 N2 C9 168.3(4) . . . . ?
C12 O6 N2 C13 93.0(4) . . . . ?
C12 O6 N2 C9 -63.8(4) . . . . ?
C10 C9 N2 C13 -97.6(4) . . . . ?
C8 C9 N2 C13 137.4(4) . . . . ?
C10 C9 N2 O6 58.0(4) . . . . ?
C8 C9 N2 O6 -67.0(4) . . . . ?
O4 C13 O5 C15 -17.2(7) . . . . ?
N2 C13 O5 C15 159.3(4) . . . . ?
O4 C13 O5 C15' 5.8(10) . . . . ?
N2 C13 O5 C15' -177.6(8) . . . . ?
C14 C15 O5 C13 172.5(3) . . . . ?
C14 C15 O5 C15' 71.6(14) . . . . ?
C14 C15' O5 C13 -168.7(7) . . . . ?
C14 C15' O5 C15 -80.4(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        65.00
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 1013940'
