# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 N O5'
_chemical_formula_weight         364.36

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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.86050(10)
_cell_length_b                   11.8631(2)
_cell_length_c                   14.0648(3)
_cell_angle_alpha                73.4260(10)
_cell_angle_beta                 83.0680(10)
_cell_angle_gamma                82.1040(10)
_cell_volume                     924.90(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             382
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8926
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         27.88
_reflns_number_total             4290
_reflns_number_gt                3436
_reflns_threshold_expression     >2sigma(I)

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

_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^)+(0.0924P)^2^+0.1502P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4290
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1487
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.400
_refine_ls_shift/su_mean         0.030

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 0.4703(2) 0.54487(10) 0.09407(8) 0.0555(3) Uani 1 1 d . . .
O2 O 1.2946(2) 0.12192(11) -0.10543(9) 0.0614(3) Uani 1 1 d . . .
O1 O 1.2084(2) 0.35376(11) 0.26507(9) 0.0599(3) Uani 1 1 d . . .
N1 N 0.8511(2) 0.38982(10) 0.07570(9) 0.0443(3) Uani 1 1 d . . .
H1A H 0.7356 0.4200 0.0409 0.053 Uiso 1 1 calc R . .
C5 C 1.1192(2) 0.34824(12) 0.19368(11) 0.0440(3) Uani 1 1 d . . .
C6 C 0.8818(2) 0.41152(12) 0.16307(10) 0.0417(3) Uani 1 1 d . . .
C7 C 0.7397(3) 0.47830(12) 0.21416(10) 0.0432(3) Uani 1 1 d . . .
O3 O 0.7726(3) 0.37938(12) 0.38145(9) 0.0747(4) Uani 1 1 d . . .
C9 C 1.2006(2) 0.28608(12) 0.11891(10) 0.0432(3) Uani 1 1 d . . .
C10 C 1.4231(3) 0.15656(13) 0.03230(12) 0.0510(4) Uani 1 1 d . . .
H10A H 1.5539 0.1048 0.0246 0.061 Uiso 1 1 calc R . .
C11 C 1.0343(2) 0.31143(11) 0.05047(10) 0.0410(3) Uani 1 1 d . . .
C12 C 1.2156(3) 0.05950(13) -0.24248(11) 0.0485(3) Uani 1 1 d . . .
O4 O 0.8496(3) 0.56719(12) 0.33201(10) 0.0728(4) Uani 1 1 d . . .
C14 C 0.7971(3) 0.48155(14) 0.31402(12) 0.0514(4) Uani 1 1 d . . .
C15 C 1.2510(3) 0.18130(13) -0.03445(11) 0.0478(3) Uani 1 1 d . . .
C16 C 1.0537(3) 0.26038(12) -0.02725(11) 0.0459(3) Uani 1 1 d . . .
H16A H 0.9416 0.2776 -0.0724 0.055 Uiso 1 1 calc R . .
C17 C 0.5272(3) 0.54722(13) 0.17441(11) 0.0459(3) Uani 1 1 d . . .
C18 C 1.3982(3) 0.20879(13) 0.10893(11) 0.0480(3) Uani 1 1 d . . .
H18A H 1.5112 0.1929 0.1534 0.058 Uiso 1 1 calc R . .
C19 C 1.1276(3) 0.13792(15) -0.17624(13) 0.0548(4) Uani 1 1 d . . .
H19A H 1.1083 0.2199 -0.2153 0.066 Uiso 1 1 calc R . .
H19B H 0.9792 0.1167 -0.1421 0.066 Uiso 1 1 calc R . .
C20 C 1.0858(3) -0.02471(16) -0.25174(13) 0.0589(4) Uani 1 1 d . . .
H20A H 0.9421 -0.0337 -0.2160 0.071 Uiso 1 1 calc R . .
C21 C 0.3829(3) 0.6210(2) 0.23446(16) 0.0718(5) Uani 1 1 d . . .
H21A H 0.2501 0.6609 0.2001 0.108 Uiso 1 1 calc R . .
H21B H 0.4728 0.6785 0.2435 0.108 Uiso 1 1 calc R . .
H21C H 0.3333 0.5711 0.2983 0.108 Uiso 1 1 calc R . .
C22 C 1.4293(3) 0.06981(17) -0.29570(13) 0.0627(4) Uani 1 1 d . . .
H22A H 1.5193 0.1261 -0.2903 0.075 Uiso 1 1 calc R . .
C23 C 1.3799(4) -0.08520(18) -0.36553(14) 0.0708(5) Uani 1 1 d . . .
H23A H 1.4351 -0.1339 -0.4065 0.085 Uiso 1 1 calc R . .
C24 C 1.1675(4) -0.09600(17) -0.31382(15) 0.0688(5) Uani 1 1 d . . .
H24A H 1.0773 -0.1516 -0.3204 0.083 Uiso 1 1 calc R . .
C25 C 1.5113(4) -0.0022(2) -0.35665(14) 0.0719(5) Uani 1 1 d . . .
H25A H 1.6558 0.0055 -0.3918 0.086 Uiso 1 1 calc R . .
C26 C 0.8420(9) 0.3689(3) 0.47973(18) 0.1440(17) Uani 1 1 d . . .
H26A H 0.8173 0.4312 0.5088 0.173 Uiso 1 1 calc R . .
C27 C 0.9412(11) 0.2653(4) 0.5235(3) 0.195(3) Uani 1 1 d . . .
H27A H 0.9800 0.2653 0.5879 0.292 Uiso 1 1 calc R . .
H27B H 1.0795 0.2474 0.4840 0.292 Uiso 1 1 calc R . .
H27C H 0.8376 0.2068 0.5310 0.292 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
O5 0.0588(6) 0.0611(7) 0.0467(6) -0.0170(5) -0.0147(5) 0.0069(5)
O2 0.0672(7) 0.0630(7) 0.0595(7) -0.0324(6) -0.0234(6) 0.0232(5)
O1 0.0656(7) 0.0654(7) 0.0560(7) -0.0255(5) -0.0243(6) 0.0032(5)
N1 0.0464(6) 0.0462(6) 0.0412(6) -0.0153(5) -0.0118(5) 0.0060(5)
C5 0.0488(7) 0.0397(7) 0.0439(7) -0.0098(5) -0.0120(6) -0.0026(5)
C6 0.0477(7) 0.0383(6) 0.0393(7) -0.0096(5) -0.0083(5) -0.0030(5)
C7 0.0500(7) 0.0414(7) 0.0392(7) -0.0123(5) -0.0076(6) -0.0020(5)
O3 0.1238(12) 0.0623(8) 0.0394(6) -0.0122(5) -0.0176(7) -0.0089(7)
C9 0.0466(7) 0.0403(7) 0.0430(7) -0.0105(5) -0.0098(6) -0.0017(5)
C10 0.0494(8) 0.0471(8) 0.0546(9) -0.0150(6) -0.0123(7) 0.0105(6)
C11 0.0452(7) 0.0361(6) 0.0396(7) -0.0083(5) -0.0067(5) 0.0005(5)
C12 0.0569(8) 0.0441(7) 0.0438(7) -0.0122(6) -0.0114(6) 0.0032(6)
O4 0.0933(10) 0.0645(8) 0.0747(8) -0.0353(7) -0.0244(7) -0.0072(7)
C14 0.0584(9) 0.0523(8) 0.0469(8) -0.0194(6) -0.0116(7) 0.0016(6)
C15 0.0562(8) 0.0426(7) 0.0443(7) -0.0144(6) -0.0102(6) 0.0058(6)
C16 0.0509(8) 0.0444(7) 0.0419(7) -0.0127(6) -0.0131(6) 0.0061(6)
C17 0.0492(7) 0.0455(7) 0.0435(7) -0.0139(6) -0.0057(6) -0.0010(6)
C18 0.0480(7) 0.0460(7) 0.0495(8) -0.0110(6) -0.0165(6) 0.0029(6)
C19 0.0580(9) 0.0539(9) 0.0541(9) -0.0205(7) -0.0145(7) 0.0093(7)
C20 0.0632(10) 0.0601(10) 0.0556(9) -0.0175(7) -0.0060(8) -0.0098(7)
C21 0.0615(10) 0.0883(13) 0.0740(12) -0.0446(10) -0.0148(9) 0.0196(9)
C22 0.0663(10) 0.0680(11) 0.0612(10) -0.0276(8) -0.0029(8) -0.0136(8)
C23 0.0945(14) 0.0712(11) 0.0535(10) -0.0313(9) -0.0117(10) 0.0027(10)
C24 0.0909(14) 0.0587(10) 0.0649(11) -0.0232(8) -0.0133(10) -0.0159(9)
C25 0.0690(11) 0.0928(14) 0.0581(10) -0.0330(10) 0.0050(9) -0.0064(10)
C26 0.290(5) 0.0956(19) 0.0519(13) -0.0255(12) -0.069(2) 0.020(2)
C27 0.348(7) 0.142(3) 0.107(2) -0.035(2) -0.139(4) 0.036(4)

_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
O5 C17 1.2250(18) . ?
O2 C15 1.3595(18) . ?
O2 C19 1.4359(19) . ?
O1 C5 1.2082(17) . ?
N1 C6 1.3622(18) . ?
N1 C11 1.4019(17) . ?
C5 C9 1.450(2) . ?
C5 C6 1.5351(19) . ?
C6 C7 1.355(2) . ?
C7 C17 1.469(2) . ?
C7 C14 1.495(2) . ?
O3 C14 1.322(2) . ?
O3 C26 1.454(2) . ?
C9 C18 1.394(2) . ?
C9 C11 1.3953(19) . ?
C10 C18 1.373(2) . ?
C10 C15 1.405(2) . ?
C11 C16 1.3797(19) . ?
C12 C20 1.379(2) . ?
C12 C22 1.381(2) . ?
C12 C19 1.499(2) . ?
O4 C14 1.201(2) . ?
C15 C16 1.398(2) . ?
C17 C21 1.497(2) . ?
C20 C24 1.384(3) . ?
C22 C25 1.379(3) . ?
C23 C24 1.367(3) . ?
C23 C25 1.371(3) . ?
C26 C27 1.298(5) . ?

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
C15 O2 C19 118.95(12) . . ?
C6 N1 C11 110.47(11) . . ?
O1 C5 C9 130.72(14) . . ?
O1 C5 C6 124.79(14) . . ?
C9 C5 C6 104.50(11) . . ?
C7 C6 N1 128.51(13) . . ?
C7 C6 C5 124.76(13) . . ?
N1 C6 C5 106.70(12) . . ?
C6 C7 C17 121.61(13) . . ?
C6 C7 C14 119.72(13) . . ?
C17 C7 C14 118.66(13) . . ?
C14 O3 C26 116.21(18) . . ?
C18 C9 C11 120.13(13) . . ?
C18 C9 C5 131.84(13) . . ?
C11 C9 C5 107.99(12) . . ?
C18 C10 C15 120.00(13) . . ?
C16 C11 C9 122.47(13) . . ?
C16 C11 N1 127.35(12) . . ?
C9 C11 N1 110.14(12) . . ?
C20 C12 C22 118.36(15) . . ?
C20 C12 C19 120.94(15) . . ?
C22 C12 C19 120.71(15) . . ?
O4 C14 O3 124.03(15) . . ?
O4 C14 C7 124.57(15) . . ?
O3 C14 C7 111.33(13) . . ?
O2 C15 C16 123.81(14) . . ?
O2 C15 C10 114.03(13) . . ?
C16 C15 C10 122.16(14) . . ?
C11 C16 C15 116.31(13) . . ?
O5 C17 C7 120.92(13) . . ?
O5 C17 C21 120.88(14) . . ?
C7 C17 C21 118.20(14) . . ?
C10 C18 C9 118.90(13) . . ?
O2 C19 C12 107.49(12) . . ?
C12 C20 C24 120.55(17) . . ?
C25 C22 C12 120.95(17) . . ?
C24 C23 C25 119.67(17) . . ?
C23 C24 C20 120.38(18) . . ?
C23 C25 C22 120.09(18) . . ?
C27 C26 O3 114.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.081
_database_code_depnum_ccdc_archive 'CCDC 945431'