# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
_publ_author_address
'Graham Bodwell'
;
Department of Chemistry
Memorial University of Newfoundland
St. Johns, NL, A1B 3X7
;
'Louise N. Dawe'
;
Department of Chemistry and
C-CART X-Ray Diffraction Laboratory
Memorial University of Newfoundland
St. Johns, NL, A1B 3X7, Canada
;
'David O. Miller'
;
Department of Chemistry
Memorial University of Newfoundland
St. Johns, NL, A1B 3X7, Canada
;
_publ_contact_author_address     
;
Add Later
;
_publ_contact_author_email       gbodwell@mun.ca
_publ_contact_author_fax         '(709) 864-3702'
_publ_contact_author_phone       '(709) 864-8406'
#TrackingRef '- AAK-4-70 CIF 2010.cif'

# SUBMISSION DETAILS

_publ_contact_author_name        'Prof. Graham Bodwell'
_publ_section_title              
;
'Add Later'
;

data_AAK-4-70
_database_code_depnum_ccdc_archive 'CCDC 828370'

_publ_section_abstract           
;
Please see full paper.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H18 N2 O5'
_chemical_formula_sum            'C25 H18 N2 O5'
_chemical_formula_weight         426.43

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   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   16.814(4)
_cell_length_b                   13.493(3)
_cell_length_c                   8.7591(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.732(5)
_cell_angle_gamma                90.00
_cell_volume                     1952.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    7975
_cell_measurement_theta_min      1.9487
_cell_measurement_theta_max      32.5311

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_process_details   '(T. Higashi, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 14.63
_diffrn_reflns_number            18140
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         26.49
_reflns_number_total             4040
_reflns_number_gt                3488
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXL-97 (Acta Cryst., 2008, A64, 112-122)'
_computing_structure_refinement  'SHELXL-97 (Acta Cryst., 2008, A64, 112-122)'
_computing_molecular_graphics    'CrystalStructure3.7.0(Rigaku/MSC Inc.,2005)'
_computing_publication_material  'CrystalStructure3.7.0(Rigaku/MSC Inc.,2005)'

_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^)+(0.0370P)^2^+1.8023P] 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         4040
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0992
_refine_ls_wR_factor_ref         0.1859
_refine_ls_wR_factor_gt          0.1784
_refine_ls_goodness_of_fit_ref   1.305
_refine_ls_restrained_S_all      1.305
_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 -0.00208(13) 0.61823(17) 0.8470(3) 0.0388(6) Uani 1 1 d . . .
O2 O -0.00339(14) 0.58796(18) 0.5996(3) 0.0435(6) Uani 1 1 d . . .
O3 O 0.38353(15) 0.4039(2) 0.7007(3) 0.0563(7) Uani 1 1 d . . .
O4 O 0.4620(2) 0.9069(3) 1.1823(5) 0.0872(11) Uani 1 1 d . . .
O5 O 0.51152(19) 0.8059(3) 1.3664(4) 0.0836(11) Uani 1 1 d . . .
N1 N 0.14419(17) 0.5009(2) 0.6507(3) 0.0386(7) Uani 1 1 d . . .
N2 N 0.4649(2) 0.8257(3) 1.2463(5) 0.0633(10) Uani 1 1 d . . .
C1 C 0.0345(2) 0.5837(2) 0.7321(4) 0.0360(7) Uani 1 1 d . . .
C2 C 0.1162(2) 0.5442(2) 0.7734(4) 0.0357(7) Uani 1 1 d . . .
C3 C 0.21211(19) 0.4334(3) 0.6966(4) 0.0368(8) Uani 1 1 d . . .
H3 H 0.1943 0.3761 0.7544 0.044 Uiso 1 1 calc R . .
C4 C 0.2450(2) 0.3951(2) 0.5577(4) 0.0381(8) Uani 1 1 d . . .
C5 C 0.1950(2) 0.3698(3) 0.4186(4) 0.0424(8) Uani 1 1 d . . .
H5 H 0.1380 0.3747 0.4102 0.051 Uiso 1 1 calc R . .
C6 C 0.2266(2) 0.3375(3) 0.2913(4) 0.0454(9) Uani 1 1 d . . .
H6 H 0.1914 0.3200 0.1973 0.055 Uiso 1 1 calc R . .
C7 C 0.3092(2) 0.3313(3) 0.3024(4) 0.0493(9) Uani 1 1 d . . .
H7 H 0.3311 0.3110 0.2151 0.059 Uiso 1 1 calc R . .
C8 C 0.3602(2) 0.3546(3) 0.4407(4) 0.0518(10) Uani 1 1 d . . .
H8 H 0.4172 0.3494 0.4487 0.062 Uiso 1 1 calc R . .
C9 C 0.3281(2) 0.3855(3) 0.5678(4) 0.0443(9) Uani 1 1 d . . .
C10 C 0.3533(2) 0.4272(3) 0.8381(4) 0.0478(9) Uani 1 1 d . . .
H10A H 0.3957 0.4628 0.9114 0.057 Uiso 1 1 calc R . .
H10B H 0.3409 0.3650 0.8887 0.057 Uiso 1 1 calc R . .
C11 C 0.2776(2) 0.4908(3) 0.8043(4) 0.0387(8) Uani 1 1 d . . .
H11 H 0.2903 0.5520 0.7489 0.046 Uiso 1 1 calc R . .
C12 C 0.2485(2) 0.5225(3) 0.9541(4) 0.0385(8) Uani 1 1 d . . .
H12 H 0.2537 0.4641 1.0254 0.046 Uiso 1 1 calc R . .
C13 C 0.1600(2) 0.5532(2) 0.9193(4) 0.0359(7) Uani 1 1 d . . .
C14 C 0.1196(2) 0.5910(2) 1.0394(4) 0.0368(8) Uani 1 1 d . . .
C15 C 0.1543(2) 0.5962(3) 1.1976(4) 0.0430(9) Uani 1 1 d . . .
H15 H 0.2090 0.5767 1.2306 0.052 Uiso 1 1 calc R . .
C16 C 0.1110(2) 0.6287(3) 1.3059(4) 0.0466(9) Uani 1 1 d . . .
H16 H 0.1362 0.6318 1.4123 0.056 Uiso 1 1 calc R . .
C17 C 0.0309(2) 0.6572(3) 1.2618(4) 0.0479(9) Uani 1 1 d . . .
H17 H 0.0015 0.6793 1.3381 0.057 Uiso 1 1 calc R . .
C18 C -0.0066(2) 0.6536(3) 1.1077(4) 0.0414(8) Uani 1 1 d . . .
H18 H -0.0614 0.6731 1.0759 0.050 Uiso 1 1 calc R . .
C19 C 0.0390(2) 0.6203(3) 1.0007(4) 0.0386(8) Uani 1 1 d . . .
C20 C 0.3047(2) 0.6040(3) 1.0334(4) 0.0381(8) Uani 1 1 d . . .
C21 C 0.2938(2) 0.7018(3) 0.9851(4) 0.0424(8) Uani 1 1 d . . .
H21 H 0.2499 0.7185 0.9043 0.051 Uiso 1 1 calc R . .
C22 C 0.3462(2) 0.7758(3) 1.0531(4) 0.0475(9) Uani 1 1 d . . .
H22 H 0.3389 0.8428 1.0200 0.057 Uiso 1 1 calc R . .
C23 C 0.4092(2) 0.7485(3) 1.1703(4) 0.0478(9) Uani 1 1 d . . .
C24 C 0.4223(2) 0.6528(3) 1.2210(4) 0.0501(10) Uani 1 1 d . . .
H24 H 0.4664 0.6366 1.3018 0.060 Uiso 1 1 calc R . .
C25 C 0.3694(2) 0.5804(3) 1.1510(4) 0.0454(9) Uani 1 1 d . . .
H25 H 0.3774 0.5135 1.1840 0.055 Uiso 1 1 calc R . .
H1 H 0.107(2) 0.484(3) 0.571(4) 0.047 Uiso 1 1 d . . .

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
O1 0.0381(13) 0.0444(13) 0.0336(12) -0.0038(10) 0.0058(10) 0.0012(10)
O2 0.0399(14) 0.0526(15) 0.0351(13) -0.0025(11) -0.0004(11) 0.0037(11)
O3 0.0357(14) 0.082(2) 0.0489(15) -0.0180(14) 0.0009(12) 0.0065(13)
O4 0.068(2) 0.061(2) 0.129(3) -0.022(2) 0.009(2) -0.0176(18)
O5 0.059(2) 0.100(3) 0.083(2) -0.034(2) -0.0100(18) -0.0181(18)
N1 0.0364(16) 0.0473(18) 0.0290(15) -0.0046(12) -0.0020(12) 0.0057(13)
N2 0.041(2) 0.073(3) 0.078(3) -0.030(2) 0.0151(19) -0.0080(19)
C1 0.0379(18) 0.0365(18) 0.0336(18) -0.0044(14) 0.0067(14) -0.0026(14)
C2 0.0371(18) 0.0392(19) 0.0295(17) 0.0029(14) 0.0030(14) 0.0006(14)
C3 0.0362(18) 0.0407(19) 0.0313(17) 0.0005(14) 0.0009(14) 0.0026(14)
C4 0.0402(19) 0.0364(18) 0.0371(18) 0.0032(15) 0.0055(15) 0.0040(15)
C5 0.042(2) 0.045(2) 0.0385(19) -0.0018(16) 0.0020(15) 0.0047(16)
C6 0.052(2) 0.043(2) 0.0382(19) 0.0010(16) 0.0022(16) 0.0072(17)
C7 0.060(2) 0.047(2) 0.043(2) -0.0009(17) 0.0148(18) 0.0063(19)
C8 0.046(2) 0.062(3) 0.050(2) -0.0050(19) 0.0151(18) 0.0059(19)
C9 0.041(2) 0.050(2) 0.040(2) -0.0032(16) 0.0024(16) 0.0014(16)
C10 0.043(2) 0.058(2) 0.0386(19) -0.0089(17) -0.0022(16) 0.0065(18)
C11 0.0401(19) 0.0413(19) 0.0326(17) 0.0024(14) 0.0017(14) -0.0014(15)
C12 0.0384(19) 0.0440(19) 0.0314(17) 0.0025(15) 0.0025(14) -0.0010(15)
C13 0.0368(18) 0.0386(18) 0.0318(17) 0.0021(14) 0.0049(14) -0.0048(15)
C14 0.0413(19) 0.0387(19) 0.0299(17) 0.0007(14) 0.0059(14) -0.0061(15)
C15 0.054(2) 0.045(2) 0.0296(18) -0.0011(15) 0.0068(16) -0.0074(17)
C16 0.062(2) 0.048(2) 0.0283(18) 0.0014(15) 0.0048(16) -0.0104(18)
C17 0.067(3) 0.040(2) 0.040(2) -0.0022(16) 0.0191(18) -0.0062(18)
C18 0.044(2) 0.0383(19) 0.043(2) -0.0025(16) 0.0124(16) -0.0011(16)
C19 0.046(2) 0.0380(18) 0.0314(17) 0.0002(14) 0.0049(15) -0.0053(15)
C20 0.0388(19) 0.046(2) 0.0287(17) -0.0028(15) 0.0043(14) -0.0005(15)
C21 0.043(2) 0.051(2) 0.0328(18) -0.0008(16) 0.0046(15) 0.0022(17)
C22 0.045(2) 0.049(2) 0.051(2) -0.0078(18) 0.0152(17) -0.0027(17)
C23 0.040(2) 0.056(2) 0.048(2) -0.0157(18) 0.0106(17) -0.0106(18)
C24 0.041(2) 0.067(3) 0.039(2) -0.0111(19) -0.0004(16) 0.0013(19)
C25 0.043(2) 0.051(2) 0.0384(19) -0.0013(17) -0.0021(16) 0.0002(17)

_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 C1 1.356(4) . ?
O1 C19 1.394(4) . ?
O2 C1 1.217(4) . ?
O3 C9 1.372(4) . ?
O3 C10 1.426(4) . ?
O4 N2 1.227(5) . ?
O5 N2 1.219(5) . ?
N1 C2 1.380(4) . ?
N1 C3 1.458(4) . ?
N1 H1 0.88(4) . ?
N2 C23 1.475(5) . ?
C1 C2 1.454(4) . ?
C2 C13 1.357(4) . ?
C3 C4 1.518(5) . ?
C3 C11 1.522(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.388(4) . ?
C4 C9 1.389(5) . ?
C5 C6 1.392(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(5) . ?
C8 H8 0.9500 . ?
C10 C11 1.518(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.544(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.519(5) . ?
C12 C20 1.530(5) . ?
C12 H12 1.0000 . ?
C13 C14 1.447(4) . ?
C14 C19 1.392(5) . ?
C14 C15 1.402(4) . ?
C15 C16 1.371(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(5) . ?
C18 H18 0.9500 . ?
C20 C21 1.388(5) . ?
C20 C25 1.388(4) . ?
C21 C22 1.390(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.369(6) . ?
C24 C25 1.386(5) . ?
C24 H24 0.9500 . ?
C25 H25 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
C1 O1 C19 120.8(3) . . ?
C9 O3 C10 117.6(3) . . ?
C2 N1 C3 114.4(3) . . ?
C2 N1 H1 116(2) . . ?
C3 N1 H1 117(2) . . ?
O5 N2 O4 123.7(4) . . ?
O5 N2 C23 119.1(4) . . ?
O4 N2 C23 117.2(4) . . ?
O2 C1 O1 117.5(3) . . ?
O2 C1 C2 123.9(3) . . ?
O1 C1 C2 118.7(3) . . ?
C13 C2 N1 124.6(3) . . ?
C13 C2 C1 121.6(3) . . ?
N1 C2 C1 113.9(3) . . ?
N1 C3 C4 112.1(3) . . ?
N1 C3 C11 107.0(3) . . ?
C4 C3 C11 109.9(3) . . ?
N1 C3 H3 109.3 . . ?
C4 C3 H3 109.3 . . ?
C11 C3 H3 109.3 . . ?
C5 C4 C9 118.1(3) . . ?
C5 C4 C3 122.4(3) . . ?
C9 C4 C3 119.5(3) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.1(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 119.9(4) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
O3 C9 C4 123.6(3) . . ?
O3 C9 C8 115.5(3) . . ?
C4 C9 C8 120.9(3) . . ?
O3 C10 C11 112.2(3) . . ?
O3 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
O3 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 C3 108.5(3) . . ?
C10 C11 C12 112.2(3) . . ?
C3 C11 C12 111.1(3) . . ?
C10 C11 H11 108.3 . . ?
C3 C11 H11 108.3 . . ?
C12 C11 H11 108.3 . . ?
C13 C12 C20 113.2(3) . . ?
C13 C12 C11 111.0(3) . . ?
C20 C12 C11 108.5(3) . . ?
C13 C12 H12 108.0 . . ?
C20 C12 H12 108.0 . . ?
C11 C12 H12 108.0 . . ?
C2 C13 C14 118.0(3) . . ?
C2 C13 C12 120.3(3) . . ?
C14 C13 C12 121.7(3) . . ?
C19 C14 C15 115.7(3) . . ?
C19 C14 C13 119.4(3) . . ?
C15 C14 C13 124.8(3) . . ?
C16 C15 C14 121.6(4) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 117.5(3) . . ?
C17 C18 H18 121.2 . . ?
C19 C18 H18 121.2 . . ?
C18 C19 C14 124.1(3) . . ?
C18 C19 O1 114.9(3) . . ?
C14 C19 O1 121.0(3) . . ?
C21 C20 C25 119.0(3) . . ?
C21 C20 C12 120.6(3) . . ?
C25 C20 C12 120.3(3) . . ?
C20 C21 C22 121.0(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 117.6(4) . . ?
C23 C22 H22 121.2 . . ?
C21 C22 H22 121.2 . . ?
C24 C23 C22 123.2(3) . . ?
C24 C23 N2 118.0(4) . . ?
C22 C23 N2 118.8(4) . . ?
C23 C24 C25 118.0(3) . . ?
C23 C24 H24 121.0 . . ?
C25 C24 H24 121.0 . . ?
C24 C25 C20 121.1(4) . . ?
C24 C25 H25 119.4 . . ?
C20 C25 H25 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.049