# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       ycheng2@bnu.edu.cn
_publ_contact_author_name        'Ying Cheng'
loop_
_publ_author_name
'Zhong-Xin Sun'
'Ying Cheng'

data_110402c_0m
_database_code_depnum_ccdc_archive 'CCDC 862111'
#TrackingRef '4a-110402c_0m.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C17 H15 N O4'

_chemical_formula_weight         297.30
_chemical_absolute_configuration unk

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           Orthorhombic

_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_

_symmetry_equiv_pos_as_xyz

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

_cell_length_a                   4.2571(7)

_cell_length_b                   14.425(2)

_cell_length_c                   23.481(4)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1441.9(4)

_cell_formula_units_Z            4

_cell_measurement_temperature    150(2)

_cell_measurement_reflns_used    2869

_cell_measurement_theta_min      2.24

_cell_measurement_theta_max      26.19

_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.32

_exptl_crystal_size_mid          0.28

_exptl_crystal_size_min          0.26

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.370

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             624

_exptl_absorpt_coefficient_mu    0.098

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9692

_exptl_absorpt_correction_T_max  0.9749

_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      150(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            8433

_diffrn_reflns_av_R_equivalents  0.0334

_diffrn_reflns_av_sigmaI/netI    0.0279

_diffrn_reflns_limit_h_min       -5

_diffrn_reflns_limit_h_max       5

_diffrn_reflns_limit_k_min       -17

_diffrn_reflns_limit_k_max       18

_diffrn_reflns_limit_l_min       -30

_diffrn_reflns_limit_l_max       14

_diffrn_reflns_theta_min         2.24

_diffrn_reflns_theta_max         27.55

_reflns_number_total             1985

_reflns_number_gt                1736

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_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^)+(0.0741P)^2^+0.2020P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   -2.0(17)

_refine_ls_number_reflns         1985

_refine_ls_number_parameters     200

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0521

_refine_ls_R_factor_gt           0.0440

_refine_ls_wR_factor_ref         0.1209

_refine_ls_wR_factor_gt          0.1157

_refine_ls_goodness_of_fit_ref   1.084

_refine_ls_restrained_S_all      1.084

_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

C1 C 0.9506(9) 0.1549(2) 0.05003(11) 0.0428(7) Uani 1 1 d . . .
H1A H 0.7511 0.1459 0.0300 0.064 Uiso 1 1 calc R . .
H1B H 1.0750 0.0979 0.0480 0.064 Uiso 1 1 calc R . .
H1C H 1.0674 0.2057 0.0322 0.064 Uiso 1 1 calc R . .
C2 C 0.7054(6) 0.25143(16) 0.11738(10) 0.0270(5) Uani 1 1 d . . .
C3 C 0.6522(7) 0.26887(15) 0.17971(10) 0.0272(5) Uani 1 1 d . . .
H3A H 0.8327 0.2445 0.2017 0.033 Uiso 1 1 calc R . .
H3B H 0.4613 0.2354 0.1923 0.033 Uiso 1 1 calc R . .
C4 C 0.6136(6) 0.37190(15) 0.19186(9) 0.0229(5) Uani 1 1 d . . .
H4 H 0.4475 0.3986 0.1666 0.027 Uiso 1 1 calc R . .
C5 C 0.5456(6) 0.39606(15) 0.25293(10) 0.0235(5) Uani 1 1 d . . .
C6 C 0.3710(6) 0.34137(17) 0.28973(10) 0.0289(5) Uani 1 1 d . . .
H6 H 0.2936 0.2830 0.2772 0.035 Uiso 1 1 calc R . .
C7 C 0.3084(7) 0.37131(18) 0.34476(11) 0.0329(6) Uani 1 1 d . . .
H7 H 0.1874 0.3336 0.3697 0.039 Uiso 1 1 calc R . .
C8 C 0.4216(8) 0.45582(18) 0.36343(10) 0.0361(6) Uani 1 1 d . . .
H8 H 0.3777 0.4761 0.4011 0.043 Uiso 1 1 calc R . .
C9 C 0.5980(7) 0.51075(17) 0.32761(10) 0.0327(6) Uani 1 1 d . . .
H9 H 0.6777 0.5685 0.3407 0.039 Uiso 1 1 calc R . .
C10 C 0.6593(6) 0.48131(16) 0.27209(9) 0.0248(5) Uani 1 1 d . . .
C11 C 0.8202(6) 0.54620(15) 0.23251(9) 0.0265(5) Uani 1 1 d . . .
C12 C 1.0025(6) 0.55557(16) 0.13127(10) 0.0261(5) Uani 1 1 d . . .
C13 C 1.1732(7) 0.63693(18) 0.13339(12) 0.0363(6) Uani 1 1 d . . .
H13 H 1.2379 0.6619 0.1689 0.044 Uiso 1 1 calc R . .
C14 C 1.2491(8) 0.68189(19) 0.08288(12) 0.0431(7) Uani 1 1 d . . .
H14 H 1.3647 0.7382 0.0842 0.052 Uiso 1 1 calc R . .
C15 C 1.1595(8) 0.64612(19) 0.03099(12) 0.0420(7) Uani 1 1 d . . .
H15 H 1.2125 0.6773 -0.0033 0.050 Uiso 1 1 calc R . .
C16 C 0.9903(9) 0.5637(2) 0.02960(12) 0.0449(8) Uani 1 1 d . . .
H16 H 0.9268 0.5387 -0.0060 0.054 Uiso 1 1 calc R . .
C17 C 0.9132(8) 0.51773(19) 0.07930(11) 0.0377(6) Uani 1 1 d . . .
H17 H 0.8004 0.4609 0.0780 0.045 Uiso 1 1 calc R . .
N1 N 0.9118(5) 0.50874(13) 0.18187(8) 0.0274(5) Uani 1 1 d . . .
O1 O 0.8890(5) 0.17749(12) 0.10897(7) 0.0363(5) Uani 1 1 d . . .
O2 O 0.5969(6) 0.29673(13) 0.07940(7) 0.0432(5) Uani 1 1 d . . .
O3 O 0.9158(4) 0.41077(10) 0.17733(7) 0.0246(4) Uani 1 1 d . . .
O4 O 0.8473(5) 0.62941(11) 0.24235(7) 0.0378(5) Uani 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

C1 0.057(2) 0.0389(14) 0.0321(13) -0.0046(11) 0.0141(14) 0.0045(15)
C2 0.0311(13) 0.0231(11) 0.0269(11) -0.0019(9) 0.0005(10) -0.0038(11)
C3 0.0293(13) 0.0221(11) 0.0302(12) 0.0003(9) 0.0032(10) 0.0009(10)
C4 0.0223(11) 0.0204(10) 0.0259(11) -0.0022(8) -0.0022(10) 0.0016(10)
C5 0.0223(11) 0.0236(10) 0.0246(11) -0.0013(9) -0.0023(10) 0.0062(9)
C6 0.0266(12) 0.0278(12) 0.0323(12) 0.0007(10) -0.0005(11) -0.0010(11)
C7 0.0351(14) 0.0336(13) 0.0299(12) 0.0058(10) 0.0033(11) 0.0058(12)
C8 0.0488(16) 0.0371(13) 0.0225(11) -0.0013(10) 0.0022(12) 0.0108(14)
C9 0.0467(16) 0.0248(11) 0.0266(11) -0.0027(9) -0.0042(12) 0.0069(12)
C10 0.0258(12) 0.0219(10) 0.0268(11) -0.0011(9) -0.0020(10) 0.0052(10)
C11 0.0297(12) 0.0224(11) 0.0272(11) -0.0019(9) -0.0039(10) 0.0033(10)
C12 0.0232(12) 0.0251(11) 0.0301(11) 0.0013(9) 0.0020(10) 0.0053(10)
C13 0.0363(15) 0.0331(13) 0.0396(13) -0.0020(11) 0.0001(12) -0.0059(13)
C14 0.0491(17) 0.0325(14) 0.0476(16) 0.0039(12) 0.0089(15) -0.0092(14)
C15 0.0509(18) 0.0370(14) 0.0381(14) 0.0087(11) 0.0063(13) -0.0013(14)
C16 0.063(2) 0.0410(15) 0.0302(13) -0.0012(11) 0.0037(14) -0.0048(15)
C17 0.0485(17) 0.0318(12) 0.0328(13) -0.0025(11) 0.0025(13) -0.0070(13)
N1 0.0330(11) 0.0186(9) 0.0305(10) -0.0016(7) 0.0029(9) 0.0007(9)
O1 0.0515(12) 0.0272(8) 0.0304(9) 0.0002(7) 0.0118(9) 0.0086(10)
O2 0.0624(14) 0.0379(10) 0.0292(9) -0.0064(8) -0.0100(10) 0.0115(11)
O3 0.0233(8) 0.0178(7) 0.0328(8) -0.0030(6) 0.0021(7) 0.0019(7)
O4 0.0571(13) 0.0215(8) 0.0348(9) -0.0044(7) 0.0017(9) -0.0014(9)

_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 O1 1.446(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.198(3) . ?
C2 O1 1.337(3) . ?
C2 C3 1.502(3) . ?
C3 C4 1.522(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.444(3) . ?
C4 C5 1.504(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.386(3) . ?
C5 C10 1.396(3) . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.486(3) . ?
C11 O4 1.228(3) . ?
C11 N1 1.363(3) . ?
C12 C13 1.381(3) . ?
C12 C17 1.390(3) . ?
C12 N1 1.420(3) . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N1 O3 1.417(2) . ?

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

O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 123.4(2) . . ?
O2 C2 C3 125.1(2) . . ?
O1 C2 C3 111.4(2) . . ?
C2 C3 C4 111.25(19) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O3 C4 C5 107.87(19) . . ?
O3 C4 C3 103.81(19) . . ?
C5 C4 C3 115.20(19) . . ?
O3 C4 H4 109.9 . . ?
C5 C4 H4 109.9 . . ?
C3 C4 H4 109.9 . . ?
C6 C5 C10 119.1(2) . . ?
C6 C5 C4 124.4(2) . . ?
C10 C5 C4 116.4(2) . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C5 120.3(2) . . ?
C9 C10 C11 118.6(2) . . ?
C5 C10 C11 120.9(2) . . ?
O4 C11 N1 121.6(2) . . ?
O4 C11 C10 122.8(2) . . ?
N1 C11 C10 115.3(2) . . ?
C13 C12 C17 120.6(2) . . ?
C13 C12 N1 121.1(2) . . ?
C17 C12 N1 118.2(2) . . ?
C12 C13 C14 119.2(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.0(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C12 119.2(3) . . ?
C16 C17 H17 120.4 . . ?
C12 C17 H17 120.4 . . ?
C11 N1 O3 117.67(19) . . ?
C11 N1 C12 128.2(2) . . ?
O3 N1 C12 114.09(18) . . ?
C2 O1 C1 115.3(2) . . ?
N1 O3 C4 111.03(17) . . ?

_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        27.55

_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.239

_refine_diff_density_min         -0.251

_refine_diff_density_rms         0.049