# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_shelxs
_database_code_depnum_ccdc_archive 'CCDC 1509399'
_audit_update_record             
;
2016-10-11 deposited with the CCDC.
2017-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N O6'
_chemical_formula_weight         281.26

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   P21

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

_cell_length_a                   9.785(2)
_cell_length_b                   11.295(2)
_cell_length_c                   11.879(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.63(3)
_cell_angle_gamma                90.00
_cell_volume                     1301.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4593
_cell_measurement_theta_min      1.8030
_cell_measurement_theta_max      31.1289

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18435
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         28.28
_reflns_number_total             5355
_reflns_number_gt                5234
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_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 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)+(0.0559P)²+0.4321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_chemical_absolute_configuration rm
_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(7)
_refine_ls_number_reflns         5355
_refine_ls_number_parameters     377
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
O10 O 0.95520(15) -0.05198(14) 1.02771(13) 0.0273(3) Uani 1 1 d . . .
H10 H 0.9058 -0.0402 1.0793 0.041 Uiso 1 1 calc R . .
O9 O 0.85789(15) 0.21235(14) 1.02550(13) 0.0287(3) Uani 1 1 d . . .
O2 O 0.17353(16) 0.35124(14) 0.39944(14) 0.0309(3) Uani 1 1 d . . .
O3 O -0.21098(15) 0.28760(14) 0.30733(13) 0.0283(3) Uani 1 1 d . . .
H3 H -0.1796 0.3352 0.2628 0.042 Uiso 1 1 calc R . .
O1 O 0.44723(15) -0.00425(15) 0.09246(13) 0.0293(3) Uani 1 1 d . . .
O6 O -0.15513(16) -0.05503(15) 0.22319(13) 0.0293(3) Uani 1 1 d . . .
H6 H -0.1465 -0.1265 0.2425 0.044 Uiso 1 1 calc R . .
O5 O 0.11010(17) 0.06288(16) 0.55562(13) 0.0324(3) Uani 1 1 d . . .
O4 O -0.03844(15) 0.29188(15) 0.49913(12) 0.0277(3) Uani 1 1 d . . .
H4 H -0.0938 0.3415 0.4660 0.041 Uiso 1 1 calc R . .
O7 O 0.46849(17) 0.27957(17) 0.54124(14) 0.0380(4) Uani 1 1 d . . .
O8 O 0.70385(16) -0.07840(15) 0.92481(14) 0.0345(4) Uani 1 1 d . . .
N2 N 1.06676(18) 0.18433(17) 0.96065(15) 0.0257(4) Uani 1 1 d . . .
C1 C 0.7648(2) 0.00244(19) 0.88439(17) 0.0248(4) Uani 1 1 d . . .
N1 N -0.1011(2) 0.02852(17) 0.45252(15) 0.0267(4) Uani 1 1 d . . .
C2 C 0.2094(2) 0.17572(19) 0.30205(17) 0.0237(4) Uani 1 1 d . . .
O12 O 1.14979(18) 0.21188(15) 0.73807(13) 0.0333(4) Uani 1 1 d . . .
H12 H 1.1387 0.1744 0.6765 0.050 Uiso 1 1 calc R . .
C3 C 0.4865(2) 0.1209(2) 0.66646(19) 0.0304(5) Uani 1 1 d . . .
H3A H 0.3928 0.1032 0.6400 0.037 Uiso 1 1 calc R . .
C4 C 0.1724(2) 0.0606(2) 0.26806(17) 0.0251(4) Uani 1 1 d . . .
H4A H 0.0932 0.0254 0.2923 0.030 Uiso 1 1 calc R . .
C5 C 0.4040(2) 0.1634(2) 0.19639(19) 0.0286(4) Uani 1 1 d . . .
H5 H 0.4830 0.1989 0.1719 0.034 Uiso 1 1 calc R . .
O11 O 1.06549(17) -0.10634(14) 0.83941(13) 0.0304(3) Uani 1 1 d . . .
H11 H 1.0799 -0.1402 0.9029 0.046 Uiso 1 1 calc R . .
C6 C 0.9146(2) 0.02589(18) 0.93596(16) 0.0226(4) Uani 1 1 d . . .
C7 C 0.2505(2) -0.0036(2) 0.19872(17) 0.0257(4) Uani 1 1 d . . .
H7 H 0.2245 -0.0820 0.1761 0.031 Uiso 1 1 calc R . .
C8 C 0.3668(2) 0.0481(2) 0.16307(18) 0.0254(4) Uani 1 1 d . . .
C9 C 0.6964(2) 0.07708(19) 0.79074(18) 0.0250(4) Uani 1 1 d . . .
C10 C 0.3265(2) 0.22573(19) 0.26467(18) 0.0273(4) Uani 1 1 d . . .
H10A H 0.3529 0.3041 0.2869 0.033 Uiso 1 1 calc R . .
C11 C 1.1415(2) 0.0929(2) 0.90750(17) 0.0251(4) Uani 1 1 d . . .
H11A H 1.2018 0.0484 0.9677 0.030 Uiso 1 1 calc R . .
C12 C 0.6898(2) 0.2380(2) 0.65406(18) 0.0289(4) Uani 1 1 d . . .
H12A H 0.7357 0.2996 0.6196 0.035 Uiso 1 1 calc R . .
C13 C 0.9402(2) 0.15368(19) 0.97889(17) 0.0235(4) Uani 1 1 d . . .
C14 C 0.7612(2) 0.1694(2) 0.74013(18) 0.0273(4) Uani 1 1 d . . .
H14 H 0.8556 0.1858 0.7648 0.033 Uiso 1 1 calc R . .
C15 C -0.0007(2) 0.2094(2) 0.41907(17) 0.0234(4) Uani 1 1 d . . .
C16 C 0.5510(2) 0.2154(2) 0.61914(17) 0.0299(5) Uani 1 1 d . . .
C17 C -0.12406(19) 0.18779(19) 0.32360(17) 0.0233(4) Uani 1 1 d . . .
H17 H -0.0896 0.1654 0.2509 0.028 Uiso 1 1 calc R . .
C18 C 1.2291(2) 0.1422(2) 0.82292(19) 0.0305(5) Uani 1 1 d . . .
H18A H 1.3036 0.1915 0.8634 0.037 Uiso 1 1 calc R . .
H18B H 1.2725 0.0760 0.7861 0.037 Uiso 1 1 calc R . .
C19 C 1.0241(2) 0.01123(18) 0.85429(17) 0.0234(4) Uani 1 1 d . . .
H19 H 0.9858 0.0441 0.7785 0.028 Uiso 1 1 calc R . .
C20 C -0.2625(2) -0.0022(2) 0.27655(19) 0.0288(4) Uani 1 1 d . . .
H20A H -0.3149 -0.0648 0.3104 0.035 Uiso 1 1 calc R . .
H20B H -0.3268 0.0403 0.2190 0.035 Uiso 1 1 calc R . .
C21 C 0.4286(2) -0.1277(2) 0.0684(2) 0.0335(5) Uani 1 1 d . . .
H21A H 0.3365 -0.1409 0.0267 0.050 Uiso 1 1 calc R . .
H21B H 0.4379 -0.1723 0.1398 0.050 Uiso 1 1 calc R . .
H21C H 0.4985 -0.1546 0.0223 0.050 Uiso 1 1 calc R . .
C22 C 0.1331(2) 0.25091(19) 0.37434(17) 0.0243(4) Uani 1 1 d . . .
C23 C -0.2033(2) 0.08395(19) 0.36850(17) 0.0247(4) Uani 1 1 d . . .
H23 H -0.2800 0.1160 0.4075 0.030 Uiso 1 1 calc R . .
C24 C 0.0124(2) 0.0913(2) 0.48247(17) 0.0270(4) Uani 1 1 d . . .
C25 C 0.5577(2) 0.0530(2) 0.75149(19) 0.0296(4) Uani 1 1 d . . .
H25 H 0.5124 -0.0105 0.7836 0.036 Uiso 1 1 calc R . .
C26 C 0.5249(3) 0.3847(3) 0.4993(2) 0.0416(6) Uani 1 1 d . . .
H26A H 0.5962 0.3635 0.4523 0.062 Uiso 1 1 calc R . .
H26B H 0.5656 0.4335 0.5633 0.062 Uiso 1 1 calc R . .
H26C H 0.4516 0.4293 0.4535 0.062 Uiso 1 1 calc R . .
H2 H 1.099(3) 0.250(3) 0.985(2) 0.038(8) Uiso 1 1 d . . .
H1 H -0.117(4) -0.043(4) 0.486(3) 0.081(12) Uiso 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
O10 C6 1.416(2) . ?
O10 H10 0.8400 . ?
O9 C13 1.230(3) . ?
O2 C22 1.224(3) . ?
O3 C17 1.410(2) . ?
O3 H3 0.8400 . ?
O1 C8 1.359(3) . ?
O1 C21 1.431(3) . ?
O6 C20 1.428(3) . ?
O6 H6 0.8400 . ?
O5 C24 1.246(3) . ?
O4 C15 1.415(3) . ?
O4 H4 0.8400 . ?
O7 C16 1.355(3) . ?
O7 C26 1.427(3) . ?
O8 C1 1.223(3) . ?
N2 C13 1.331(3) . ?
N2 C11 1.457(3) . ?
N2 H2 0.84(3) . ?
C1 C9 1.483(3) . ?
C1 C6 1.534(3) . ?
N1 C24 1.326(3) . ?
N1 C23 1.457(3) . ?
N1 H1 0.92(5) . ?
C2 C4 1.395(3) . ?
C2 C10 1.402(3) . ?
C2 C22 1.478(3) . ?
O12 C18 1.425(3) . ?
O12 H12 0.8400 . ?
C3 C25 1.381(3) . ?
C3 C16 1.396(3) . ?
C3 H3A 0.9500 . ?
C4 C7 1.398(3) . ?
C4 H4A 0.9500 . ?
C5 C10 1.375(3) . ?
C5 C8 1.396(3) . ?
C5 H5 0.9500 . ?
O11 C19 1.406(2) . ?
O11 H11 0.8400 . ?
C6 C13 1.540(3) . ?
C6 C19 1.547(3) . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C9 C14 1.397(3) . ?
C9 C25 1.402(3) . ?
C10 H10A 0.9500 . ?
C11 C18 1.511(3) . ?
C11 C19 1.542(3) . ?
C11 H11A 1.0000 . ?
C12 C16 1.390(3) . ?
C12 C14 1.394(3) . ?
C12 H12A 0.9500 . ?
C14 H14 0.9500 . ?
C15 C24 1.529(3) . ?
C15 C22 1.550(3) . ?
C15 C17 1.562(3) . ?
C17 C23 1.540(3) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19 1.0000 . ?
C20 C23 1.519(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C23 H23 1.0000 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C6 O10 H10 109.5 . . ?
C17 O3 H3 109.5 . . ?
C8 O1 C21 118.55(18) . . ?
C20 O6 H6 109.5 . . ?
C15 O4 H4 109.5 . . ?
C16 O7 C26 117.42(18) . . ?
C13 N2 C11 114.69(18) . . ?
C13 N2 H2 119(2) . . ?
C11 N2 H2 126(2) . . ?
O8 C1 C9 121.57(18) . . ?
O8 C1 C6 117.51(18) . . ?
C9 C1 C6 120.90(18) . . ?
C24 N1 C23 115.37(18) . . ?
C24 N1 H1 122(2) . . ?
C23 N1 H1 122(2) . . ?
C4 C2 C10 118.37(19) . . ?
C4 C2 C22 124.91(19) . . ?
C10 C2 C22 116.71(18) . . ?
C18 O12 H12 109.5 . . ?
C25 C3 C16 120.5(2) . . ?
C25 C3 H3A 119.8 . . ?
C16 C3 H3A 119.8 . . ?
C2 C4 C7 120.9(2) . . ?
C2 C4 H4A 119.6 . . ?
C7 C4 H4A 119.6 . . ?
C10 C5 C8 120.1(2) . . ?
C10 C5 H5 120.0 . . ?
C8 C5 H5 120.0 . . ?
C19 O11 H11 109.5 . . ?
O10 C6 C1 110.84(17) . . ?
O10 C6 C13 108.10(16) . . ?
C1 C6 C13 113.49(16) . . ?
O10 C6 C19 105.62(15) . . ?
C1 C6 C19 115.81(16) . . ?
C13 C6 C19 102.26(16) . . ?
C8 C7 C4 119.6(2) . . ?
C8 C7 H7 120.2 . . ?
C4 C7 H7 120.2 . . ?
O1 C8 C7 124.7(2) . . ?
O1 C8 C5 115.45(19) . . ?
C7 C8 C5 119.8(2) . . ?
C14 C9 C25 118.4(2) . . ?
C14 C9 C1 124.19(18) . . ?
C25 C9 C1 117.39(19) . . ?
C5 C10 C2 121.2(2) . . ?
C5 C10 H10A 119.4 . . ?
C2 C10 H10A 119.4 . . ?
N2 C11 C18 112.86(19) . . ?
N2 C11 C19 102.23(16) . . ?
C18 C11 C19 113.92(18) . . ?
N2 C11 H11A 109.2 . . ?
C18 C11 H11A 109.2 . . ?
C19 C11 H11A 109.2 . . ?
C16 C12 C14 119.4(2) . . ?
C16 C12 H12A 120.3 . . ?
C14 C12 H12A 120.3 . . ?
O9 C13 N2 127.7(2) . . ?
O9 C13 C6 124.52(19) . . ?
N2 C13 C6 107.68(18) . . ?
C12 C14 C9 121.26(19) . . ?
C12 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
O4 C15 C24 104.81(16) . . ?
O4 C15 C22 109.83(17) . . ?
C24 C15 C22 114.42(17) . . ?
O4 C15 C17 110.22(16) . . ?
C24 C15 C17 103.14(17) . . ?
C22 C15 C17 113.90(16) . . ?
O7 C16 C12 125.2(2) . . ?
O7 C16 C3 115.06(19) . . ?
C12 C16 C3 119.8(2) . . ?
O3 C17 C23 109.51(16) . . ?
O3 C17 C15 111.62(17) . . ?
C23 C17 C15 104.12(16) . . ?
O3 C17 H17 110.5 . . ?
C23 C17 H17 110.5 . . ?
C15 C17 H17 110.5 . . ?
O12 C18 C11 111.74(18) . . ?
O12 C18 H18A 109.3 . . ?
C11 C18 H18A 109.3 . . ?
O12 C18 H18B 109.3 . . ?
C11 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
O11 C19 C11 113.88(16) . . ?
O11 C19 C6 114.52(17) . . ?
C11 C19 C6 102.67(16) . . ?
O11 C19 H19 108.5 . . ?
C11 C19 H19 108.5 . . ?
C6 C19 H19 108.5 . . ?
O6 C20 C23 110.77(17) . . ?
O6 C20 H20A 109.5 . . ?
C23 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
C23 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 C2 120.12(19) . . ?
O2 C22 C15 117.18(19) . . ?
C2 C22 C15 122.69(18) . . ?
N1 C23 C20 112.26(18) . . ?
N1 C23 C17 103.46(16) . . ?
C20 C23 C17 113.59(17) . . ?
N1 C23 H23 109.1 . . ?
C20 C23 H23 109.1 . . ?
C17 C23 H23 109.1 . . ?
O5 C24 N1 126.0(2) . . ?
O5 C24 C15 125.1(2) . . ?
N1 C24 C15 108.79(18) . . ?
C3 C25 C9 120.5(2) . . ?
C3 C25 H25 119.7 . . ?
C9 C25 H25 119.7 . . ?
O7 C26 H26A 109.5 . . ?
O7 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O7 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_shelxs
_database_code_depnum_ccdc_archive 'CCDC 1509400'
_audit_update_record             
;
2016-10-11 deposited with the CCDC.
2017-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 O6'
_chemical_formula_weight         320.30

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 21'

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

_cell_length_a                   7.4743(15)
_cell_length_b                   9.2516(19)
_cell_length_c                   10.829(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.25(3)
_cell_angle_gamma                90.00
_cell_volume                     748.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    2208
_cell_measurement_theta_min      2.2014
_cell_measurement_theta_max      30.9287

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.44
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9526
_exptl_absorpt_correction_T_max  0.9526
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(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            6392
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         30.96
_reflns_number_total             3900
_reflns_number_gt                3833
_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 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)+(0.0521P)²+0.0936P] 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
_chemical_absolute_configuration rm
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(6)
_refine_ls_number_reflns         3900
_refine_ls_number_parameters     214
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.003
_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
N2 N 0.18098(12) 0.14016(11) 0.47970(8) 0.01970(18) Uani 1 1 d . . .
O1 O 0.18559(12) 0.35554(10) 0.24555(8) 0.02620(18) Uani 1 1 d . . .
O2 O -0.17953(12) 0.16722(11) 0.11813(8) 0.0294(2) Uani 1 1 d . . .
O4 O -0.08771(12) 0.26284(12) 0.46105(8) 0.02866(19) Uani 1 1 d . . .
O5 O 0.27095(14) 0.02885(12) 0.17791(8) 0.0339(2) Uani 1 1 d . . .
O6 O 0.42662(12) 0.28416(10) 0.48360(8) 0.02604(18) Uani 1 1 d . . .
O3 O -0.09743(14) -0.01043(11) 0.29227(9) 0.0335(2) Uani 1 1 d . . .
C1 C 0.02428(14) 0.18354(13) 0.41945(10) 0.0209(2) Uani 1 1 d . . .
C2 C 0.35169(14) 0.17570(13) 0.68026(10) 0.0208(2) Uani 1 1 d . . .
C3 C 0.28196(15) 0.24043(12) 0.55936(10) 0.0210(2) Uani 1 1 d . . .
H3A H 0.2056 0.3263 0.5768 0.025 Uiso 1 1 calc R . .
C4 C 0.33384(16) 0.03055(13) 0.71027(10) 0.0247(2) Uani 1 1 d . . .
H4 H 0.2746 -0.0337 0.6538 0.030 Uiso 1 1 calc R . .
C5 C -0.05373(15) 0.20993(13) 0.18520(10) 0.0224(2) Uani 1 1 d . . .
C6 C 0.40326(17) -0.02088(15) 0.82392(11) 0.0289(2) Uani 1 1 d . . .
H6 H 0.3911 -0.1201 0.8445 0.035 Uiso 1 1 calc R . .
C7 C 0.30672(15) 0.06702(13) 0.39992(9) 0.0219(2) Uani 1 1 d . . .
H7 H 0.3313 -0.0336 0.4298 0.026 Uiso 1 1 calc R . .
C8 C 0.20917(16) 0.06464(13) 0.27406(10) 0.0235(2) Uani 1 1 d . . .
C9 C 0.44038(16) 0.26879(14) 0.76372(10) 0.0255(2) Uani 1 1 d . . .
H9 H 0.4537 0.3679 0.7431 0.031 Uiso 1 1 calc R . .
N1 N 0.03168(14) 0.33434(12) 0.16878(9) 0.0261(2) Uani 1 1 d . . .
C10 C 0.50932(17) 0.21797(15) 0.87660(11) 0.0286(2) Uani 1 1 d . . .
H10 H 0.5694 0.2820 0.9329 0.034 Uiso 1 1 calc R . .
C11 C 0.01407(15) 0.11210(12) 0.29128(10) 0.0216(2) Uani 1 1 d . . .
C12 C 0.48979(17) 0.07270(16) 0.90661(10) 0.0292(3) Uani 1 1 d . . .
H12 H 0.5358 0.0375 0.9839 0.035 Uiso 1 1 calc R . .
C13 C 0.47732(16) 0.16083(15) 0.41313(11) 0.0276(2) Uani 1 1 d . . .
H13A H 0.5753 0.1069 0.4567 0.033 Uiso 1 1 calc R . .
H13B H 0.5178 0.1906 0.3310 0.033 Uiso 1 1 calc R . .
C14 C 0.17263(19) 0.49118(15) 0.31140(13) 0.0317(3) Uani 1 1 d . . .
H14A H 0.1617 0.5708 0.2519 0.048 Uiso 1 1 calc R . .
H14B H 0.2804 0.5050 0.3646 0.048 Uiso 1 1 calc R . .
H14C H 0.0670 0.4895 0.3622 0.048 Uiso 1 1 calc R . .
C15 C 0.0232(2) 0.4157(2) 0.05356(14) 0.0434(4) Uani 1 1 d . . .
H15A H 0.1322 0.3982 0.0084 0.065 Uiso 1 1 calc R . .
H15B H 0.0131 0.5190 0.0717 0.065 Uiso 1 1 calc R . .
H15C H -0.0815 0.3845 0.0030 0.065 Uiso 1 1 calc R . .
H1 H -0.168(3) 0.006(3) 0.223(2) 0.057(6) Uiso 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
N2 C1 1.3778(14) . ?
N2 C3 1.4571(14) . ?
N2 C7 1.4668(14) . ?
O1 N1 1.4063(13) . ?
O1 C14 1.4484(17) . ?
O2 C5 1.2304(14) . ?
O4 C1 1.2130(15) . ?
O5 C8 1.2020(15) . ?
O6 C13 1.4320(16) . ?
O6 C3 1.4407(15) . ?
O3 C11 1.4073(14) . ?
O3 H1 0.91(2) . ?
C1 C11 1.5365(15) . ?
C2 C4 1.3893(17) . ?
C2 C9 1.3967(16) . ?
C2 C3 1.5135(15) . ?
C3 H3A 1.0000 . ?
C4 C6 1.4000(16) . ?
C4 H4 0.9500 . ?
C5 N1 1.3315(16) . ?
C5 C11 1.5329(15) . ?
C6 C12 1.3872(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.5204(15) . ?
C7 C13 1.5444(17) . ?
C7 H7 1.0000 . ?
C8 C11 1.5413(17) . ?
C9 C10 1.3897(16) . ?
C9 H9 0.9500 . ?
N1 C15 1.4562(16) . ?
C10 C12 1.392(2) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 N2 C3 120.38(10) . . ?
C1 N2 C7 114.08(9) . . ?
C3 N2 C7 108.27(9) . . ?
N1 O1 C14 110.05(10) . . ?
C13 O6 C3 107.46(9) . . ?
C11 O3 H1 100.5(15) . . ?
O4 C1 N2 125.91(10) . . ?
O4 C1 C11 125.81(10) . . ?
N2 C1 C11 108.27(10) . . ?
C4 C2 C9 119.48(10) . . ?
C4 C2 C3 123.50(10) . . ?
C9 C2 C3 117.02(11) . . ?
O6 C3 N2 102.97(8) . . ?
O6 C3 C2 111.29(9) . . ?
N2 C3 C2 114.39(9) . . ?
O6 C3 H3A 109.3 . . ?
N2 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C2 C4 C6 119.90(11) . . ?
C2 C4 H4 120.0 . . ?
C6 C4 H4 120.0 . . ?
O2 C5 N1 123.92(11) . . ?
O2 C5 C11 118.37(11) . . ?
N1 C5 C11 117.67(10) . . ?
C12 C6 C4 120.17(12) . . ?
C12 C6 H6 119.9 . . ?
C4 C6 H6 119.9 . . ?
N2 C7 C8 103.82(9) . . ?
N2 C7 C13 103.41(9) . . ?
C8 C7 C13 117.15(10) . . ?
N2 C7 H7 110.6 . . ?
C8 C7 H7 110.6 . . ?
C13 C7 H7 110.6 . . ?
O5 C8 C7 126.40(11) . . ?
O5 C8 C11 125.51(10) . . ?
C7 C8 C11 108.06(9) . . ?
C10 C9 C2 120.71(12) . . ?
C10 C9 H9 119.6 . . ?
C2 C9 H9 119.6 . . ?
C5 N1 O1 115.28(9) . . ?
C5 N1 C15 123.78(11) . . ?
O1 N1 C15 116.21(11) . . ?
C9 C10 C12 119.57(11) . . ?
C9 C10 H10 120.2 . . ?
C12 C10 H10 120.2 . . ?
O3 C11 C5 107.63(9) . . ?
O3 C11 C1 110.36(9) . . ?
C5 C11 C1 115.23(10) . . ?
O3 C11 C8 109.56(10) . . ?
C5 C11 C8 111.35(9) . . ?
C1 C11 C8 102.61(9) . . ?
C6 C12 C10 120.16(11) . . ?
C6 C12 H12 119.9 . . ?
C10 C12 H12 119.9 . . ?
O6 C13 C7 105.21(9) . . ?
O6 C13 H13A 110.7 . . ?
C7 C13 H13A 110.7 . . ?
O6 C13 H13B 110.7 . . ?
C7 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.895
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.043
