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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_111
_audit_block_doi                 10.5517/ccz8nnj
_database_code_depnum_ccdc_archive 'CCDC 902058'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tetlet.2012.10.018 2012
_audit_update_record             
;
2012-09-19 deposited with the CCDC.
2014-12-02 downloaded from the CCDC.
;
#TrackingRef 'Final CIF.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N2 O8'
_chemical_formula_weight         388.33

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

_cell_length_a                   5.830(3)
_cell_length_b                   9.556(4)
_cell_length_c                   31.119(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1733.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    771
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      22.42

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9882
_exptl_absorpt_correction_T_max  0.9929
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4171
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_sigmaI/netI    0.1081
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2858
_reflns_number_gt                1945
_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    'MERCURY 2.3'
_computing_publication_material  'ORTEP 3V.2'

_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)+(0.1000P)²+0.1428P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         2858
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1866
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002

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
O4 O 0.8586(7) 0.3524(5) -0.08415(13) 0.0264(11) Uani 1 1 d . . .
O3 O 0.5696(7) 0.4535(5) -0.11501(13) 0.0287(11) Uani 1 1 d . . .
O5 O 0.9190(7) 0.3388(4) 0.07324(12) 0.0200(10) Uani 1 1 d . . .
O1 O 0.0011(6) 0.6590(4) 0.04053(13) 0.0221(10) Uani 1 1 d . . .
O2 O -0.0264(7) 0.6612(4) -0.02921(13) 0.0243(11) Uani 1 1 d . . .
N1 N 0.0709(8) 0.6269(5) 0.00465(17) 0.0184(11) Uani 1 1 d . . .
N2 N 0.6731(8) 0.4113(5) -0.08332(15) 0.0186(12) Uani 1 1 d . . .
C6 C 0.5674(9) 0.4380(6) -0.04087(17) 0.0149(13) Uani 1 1 d . . .
C2 C 0.2815(9) 0.5422(6) 0.00097(18) 0.0147(13) Uani 1 1 d . . .
C4 C 0.5952(9) 0.4299(6) 0.03569(16) 0.0122(12) Uani 1 1 d . . .
C7 C 0.7376(9) 0.3989(6) 0.07448(18) 0.0151(13) Uani 1 1 d . . .
C5 C 0.6841(9) 0.3951(6) -0.00473(17) 0.0144(13) Uani 1 1 d . . .
H5 H 0.8193 0.3441 -0.0071 0.017 Uiso 1 1 calc R . .
C3 C 0.3910(9) 0.5041(6) 0.03873(18) 0.0134(13) Uani 1 1 d . . .
H3 H 0.3294 0.5276 0.0653 0.016 Uiso 1 1 calc R . .
C1 C 0.3669(9) 0.5106(6) -0.03914(18) 0.0162(13) Uani 1 1 d . . .
H1 H 0.2906 0.5377 -0.0640 0.019 Uiso 1 1 calc R . .
O6 O 0.6391(6) 0.4511(4) 0.10981(11) 0.0169(9) Uani 1 1 d . . .
C9 C 0.7278(10) 0.3177(6) 0.17429(18) 0.0207(14) Uani 1 1 d . . .
H9 H 0.5793 0.2823 0.1756 0.025 Uiso 1 1 calc R . .
C8 C 0.7680(9) 0.4493(6) 0.15061(17) 0.0154(13) Uani 1 1 d . . .
H8 H 0.9322 0.4586 0.1445 0.019 Uiso 1 1 calc R . .
C10 C 0.8918(12) 0.2490(7) 0.1935(2) 0.0312(17) Uani 1 1 d . . .
H10A H 1.0415 0.2825 0.1926 0.037 Uiso 1 1 calc R . .
H10B H 0.8591 0.1664 0.2081 0.037 Uiso 1 1 calc R . .
O7 O 0.2886(6) 0.5050(4) 0.18418(12) 0.0222(10) Uani 1 1 d . . .
O8 O 0.3527(6) 0.7116(4) 0.15383(13) 0.0222(10) Uani 1 1 d . . .
C13 C 0.7865(9) 0.6175(6) 0.21754(17) 0.0159(14) Uani 1 1 d . . .
H13A H 0.9300 0.5698 0.2235 0.019 Uiso 1 1 calc R . .
H13B H 0.6795 0.6062 0.2412 0.019 Uiso 1 1 calc R . .
C11 C 0.5439(9) 0.8057(6) 0.14343(18) 0.0195(14) Uani 1 1 d . . .
H11 H 0.5451 0.8318 0.1130 0.023 Uiso 1 1 calc R . .
C12 C 0.7601(9) 0.7263(6) 0.15630(18) 0.0153(13) Uani 1 1 d . . .
H12 H 0.8871 0.7270 0.1357 0.018 Uiso 1 1 calc R . .
C14 C 0.8171(9) 0.7719(6) 0.20281(18) 0.0175(14) Uani 1 1 d . . .
H14 H 0.9731 0.8083 0.2065 0.021 Uiso 1 1 calc R . .
C16 C 0.5363(11) 0.9329(6) 0.17254(18) 0.0221(14) Uani 1 1 d . . .
H16A H 0.3809 0.9678 0.1756 0.027 Uiso 1 1 calc R . .
H16B H 0.6333 1.0073 0.1616 0.027 Uiso 1 1 calc R . .
C15 C 0.6278(10) 0.8758(7) 0.21532(18) 0.0241(16) Uani 1 1 d . . .
H15A H 0.5069 0.8290 0.2312 0.029 Uiso 1 1 calc R . .
H15B H 0.6894 0.9508 0.2329 0.029 Uiso 1 1 calc R . .
C17 C 0.6829(9) 0.5821(6) 0.17294(17) 0.0147(13) Uani 1 1 d . . .
C18 C 0.4241(10) 0.5892(7) 0.17156(17) 0.0168(13) 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
O4 N2 1.220(6) . ?
O3 N2 1.224(6) . ?
O5 C7 1.204(6) . ?
O1 N1 1.227(6) . ?
O2 N1 1.241(6) . ?
N1 C2 1.475(7) . ?
N2 C6 1.480(7) . ?
C6 C1 1.360(8) . ?
C6 C5 1.377(7) . ?
C2 C1 1.377(8) . ?
C2 C3 1.386(8) . ?
C4 C3 1.389(7) . ?
C4 C5 1.400(7) . ?
C4 C7 1.495(7) . ?
C7 O6 1.337(6) . ?
O6 C8 1.475(6) . ?
C9 C10 1.305(8) . ?
C9 C8 1.476(8) . ?
C8 C17 1.530(8) . ?
O7 C18 1.194(7) . ?
O8 C18 1.358(7) . ?
O8 C11 1.469(7) . ?
C13 C17 1.551(7) . ?
C13 C14 1.555(8) . ?
C11 C16 1.516(8) . ?
C11 C12 1.525(8) . ?
C12 C17 1.539(8) . ?
C12 C14 1.548(8) . ?
C14 C15 1.534(8) . ?
C16 C15 1.535(8) . ?
C17 C18 1.511(8) . ?

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 N1 O2 123.7(5) . . ?
O1 N1 C2 118.9(5) . . ?
O2 N1 C2 117.4(5) . . ?
O4 N2 O3 124.9(5) . . ?
O4 N2 C6 117.9(5) . . ?
O3 N2 C6 117.2(5) . . ?
C1 C6 C5 123.0(5) . . ?
C1 C6 N2 118.8(5) . . ?
C5 C6 N2 118.2(5) . . ?
C1 C2 C3 123.0(5) . . ?
C1 C2 N1 119.5(5) . . ?
C3 C2 N1 117.5(5) . . ?
C3 C4 C5 119.9(5) . . ?
C3 C4 C7 121.5(5) . . ?
C5 C4 C7 118.2(5) . . ?
O5 C7 O6 125.6(5) . . ?
O5 C7 C4 123.8(5) . . ?
O6 C7 C4 110.6(5) . . ?
C6 C5 C4 118.7(5) . . ?
C2 C3 C4 118.1(5) . . ?
C6 C1 C2 117.3(5) . . ?
C7 O6 C8 119.0(4) . . ?
C10 C9 C8 122.8(6) . . ?
C9 C8 O6 111.0(4) . . ?
C9 C8 C17 115.4(5) . . ?
O6 C8 C17 102.5(4) . . ?
C18 O8 C11 112.6(4) . . ?
C17 C13 C14 89.3(4) . . ?
O8 C11 C16 109.7(4) . . ?
O8 C11 C12 105.3(4) . . ?
C16 C11 C12 105.4(5) . . ?
C11 C12 C17 107.0(4) . . ?
C11 C12 C14 106.4(5) . . ?
C17 C12 C14 90.0(4) . . ?
C15 C14 C12 105.4(5) . . ?
C15 C14 C13 117.1(5) . . ?
C12 C14 C13 89.1(4) . . ?
C11 C16 C15 102.9(5) . . ?
C16 C15 C14 105.1(5) . . ?
C18 C17 C8 110.4(5) . . ?
C18 C17 C12 104.0(5) . . ?
C8 C17 C12 119.7(4) . . ?
C18 C17 C13 113.9(5) . . ?
C8 C17 C13 117.5(5) . . ?
C12 C17 C13 89.5(4) . . ?
O7 C18 O8 120.7(5) . . ?
O7 C18 C17 128.4(6) . . ?
O8 C18 C17 110.9(5) . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.144


