# 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/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_psy-01
_database_code_depnum_ccdc_archive 'CCDC 1032943'
_audit_update_record             
;
2014-11-06 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 N O4'
_chemical_formula_sum            'C13 H17 N O4'
_chemical_formula_weight         251.28
_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           monoclinic
_symmetry_space_group_name_H-M   'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'

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

_cell_length_a                   7.4735(6)
_cell_length_b                   23.4154(11)
_cell_length_c                   7.4325(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.242(3)
_cell_angle_gamma                90.00
_cell_volume                     1271.07(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6201
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.4

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9438
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_process_details   'Higashi, T. (1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4614
_diffrn_reflns_av_R_equivalents  0.0963
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1123
_reflns_number_gt                1024
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0890P)²+0.7097P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.055(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1123
_refine_ls_number_parameters     164
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1543
_refine_ls_wR_factor_gt          0.1505
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.003
_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 0.4657(7) 0.29586(19) 0.7727(8) 0.0615(13) Uani 1 1 d . . .
C2 C 0.2873(8) 0.3255(2) 0.7584(8) 0.0658(13) Uani 1 1 d . . .
H2A H 0.2751 0.3393 0.8782 0.079 Uiso 1 1 calc R . .
H2B H 0.1869 0.2995 0.7121 0.079 Uiso 1 1 calc R . .
C3 C 0.2854(7) 0.37560(19) 0.6246(6) 0.0533(11) Uani 1 1 d . . .
H3A H 0.1760 0.3983 0.6201 0.064 Uiso 1 1 calc R . .
H3B H 0.3909 0.3998 0.6686 0.064 Uiso 1 1 calc R . .
C4 C 0.2894(5) 0.35419(16) 0.4321(6) 0.0417(9) Uani 1 1 d . . .
H4 H 0.1754 0.3328 0.3902 0.050 Uiso 1 1 calc R . .
C5 C 0.2865(5) 0.40304(18) 0.2923(5) 0.0444(9) Uani 1 1 d . . .
H5 H 0.3031 0.3868 0.1754 0.053 Uiso 1 1 calc R . .
C6 C 0.4327(8) 0.4466(2) 0.3562(7) 0.0690(14) Uani 1 1 d . . .
H6 H 0.3981 0.4825 0.3908 0.083 Uiso 1 1 calc R . .
C7 C 0.6100(10) 0.4366(4) 0.3659(10) 0.096(2) Uani 1 1 d . . .
H7 H 0.6920 0.4664 0.4019 0.115 Uiso 1 1 calc R . .
C8 C 0.6854(8) 0.3800(4) 0.3221(10) 0.103(3) Uani 1 1 d . . .
H8A H 0.6396 0.3717 0.1927 0.123 Uiso 1 1 calc R . .
H8B H 0.8176 0.3828 0.3428 0.123 Uiso 1 1 calc R . .
C9 C 0.6376(6) 0.3320(3) 0.4322(7) 0.0719(17) Uani 1 1 d . . .
C10 C 0.4470(6) 0.3114(2) 0.4293(6) 0.0561(13) Uani 1 1 d . . .
H10 H 0.4098 0.2883 0.3176 0.067 Uiso 1 1 calc R . .
C11 C 0.4914(8) 0.2696(2) 0.5911(9) 0.0749(18) Uani 1 1 d . . .
H11 H 0.4130 0.2358 0.5632 0.090 Uiso 1 1 calc R . .
C12 C 0.0639(9) 0.46524(19) 0.1152(7) 0.0632(13) Uani 1 1 d . . .
H12A H 0.1571 0.4947 0.1280 0.076 Uiso 1 1 calc R . .
H12B H -0.0519 0.4837 0.1166 0.076 Uiso 1 1 calc R . .
C13 C -0.0977(9) 0.3996(3) -0.0990(9) 0.0822(17) Uani 1 1 d . . .
H13A H -0.0992 0.3822 -0.2163 0.123 Uiso 1 1 calc R . .
H13B H -0.2098 0.4202 -0.1043 0.123 Uiso 1 1 calc R . .
H13C H -0.0857 0.3705 -0.0062 0.123 Uiso 1 1 calc R . .
N1 N 0.7622(7) 0.2998(4) 0.5214(8) 0.098(2) Uani 1 1 d . . .
O1 O 0.5871(6) 0.29369(19) 0.9087(6) 0.0823(13) Uani 1 1 d . . .
O2 O 0.6761(7) 0.2537(3) 0.5998(8) 0.1036(18) Uani 1 1 d . . .
O3 O 0.1072(4) 0.42780(12) 0.2657(4) 0.0513(8) Uani 1 1 d . . .
O4 O 0.0512(6) 0.43754(15) -0.0554(5) 0.0691(11) 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
C1 O1 1.207(6) . ?
C1 C2 1.487(8) . ?
C1 C11 1.532(9) . ?
C2 C3 1.537(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.522(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.542(5) . ?
C4 C10 1.550(6) . ?
C4 H4 0.9800 . ?
C5 O3 1.434(5) . ?
C5 C6 1.497(7) . ?
C5 H5 0.9800 . ?
C6 C7 1.333(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.503(12) . ?
C7 H7 0.9300 . ?
C8 C9 1.477(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.270(8) . ?
C9 C10 1.500(7) . ?
C10 C11 1.532(8) . ?
C10 H10 0.9800 . ?
C11 O2 1.418(7) . ?
C11 H11 0.9800 . ?
C12 O3 1.404(5) . ?
C12 O4 1.409(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O4 1.407(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 O2 1.443(10) . ?

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 C2 125.6(6) . . ?
O1 C1 C11 120.6(5) . . ?
C2 C1 C11 113.7(4) . . ?
C1 C2 C3 106.7(4) . . ?
C1 C2 H2A 110.4 . . ?
C3 C2 H2A 110.4 . . ?
C1 C2 H2B 110.4 . . ?
C3 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C4 C3 C2 110.9(4) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C5 112.9(3) . . ?
C3 C4 C10 113.1(3) . . ?
C5 C4 C10 111.9(4) . . ?
C3 C4 H4 106.1 . . ?
C5 C4 H4 106.1 . . ?
C10 C4 H4 106.1 . . ?
O3 C5 C6 111.5(4) . . ?
O3 C5 C4 105.8(3) . . ?
C6 C5 C4 112.8(4) . . ?
O3 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
C7 C6 C5 123.2(6) . . ?
C7 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C6 C7 C8 123.9(6) . . ?
C6 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C9 C8 C7 113.9(5) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
N1 C9 C8 120.3(6) . . ?
N1 C9 C10 113.9(6) . . ?
C8 C9 C10 125.3(5) . . ?
C9 C10 C11 98.5(4) . . ?
C9 C10 C4 120.9(4) . . ?
C11 C10 C4 116.2(4) . . ?
C9 C10 H10 106.7 . . ?
C11 C10 H10 106.7 . . ?
C4 C10 H10 106.7 . . ?
O2 C11 C1 111.6(4) . . ?
O2 C11 C10 104.5(6) . . ?
C1 C11 C10 112.8(4) . . ?
O2 C11 H11 109.3 . . ?
C1 C11 H11 109.3 . . ?
C10 C11 H11 109.3 . . ?
O3 C12 O4 112.9(3) . . ?
O3 C12 H12A 109.0 . . ?
O4 C12 H12A 109.0 . . ?
O3 C12 H12B 109.0 . . ?
O4 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 N1 O2 108.4(5) . . ?
C11 O2 N1 107.3(5) . . ?
C12 O3 C5 114.4(4) . . ?
C13 O4 C12 113.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 113.4(6) . . . . ?
C11 C1 C2 C3 -63.4(6) . . . . ?
C1 C2 C3 C4 64.5(6) . . . . ?
C2 C3 C4 C5 179.7(4) . . . . ?
C2 C3 C4 C10 -52.1(5) . . . . ?
C3 C4 C5 O3 -69.3(4) . . . . ?
C10 C4 C5 O3 161.8(3) . . . . ?
C3 C4 C5 C6 52.7(5) . . . . ?
C10 C4 C5 C6 -76.2(5) . . . . ?
O3 C5 C6 C7 -170.2(5) . . . . ?
C4 C5 C6 C7 71.0(7) . . . . ?
C5 C6 C7 C8 -2.8(10) . . . . ?
C6 C7 C8 C9 -56.7(9) . . . . ?
C7 C8 C9 N1 -126.8(6) . . . . ?
C7 C8 C9 C10 62.5(8) . . . . ?
N1 C9 C10 C11 17.6(5) . . . . ?
C8 C9 C10 C11 -171.2(6) . . . . ?
N1 C9 C10 C4 145.1(5) . . . . ?
C8 C9 C10 C4 -43.7(7) . . . . ?
C3 C4 C10 C9 -81.7(5) . . . . ?
C5 C4 C10 C9 47.0(5) . . . . ?
C3 C4 C10 C11 37.3(5) . . . . ?
C5 C4 C10 C11 166.1(4) . . . . ?
O1 C1 C11 O2 -10.4(8) . . . . ?
C2 C1 C11 O2 166.5(5) . . . . ?
O1 C1 C11 C10 -127.8(5) . . . . ?
C2 C1 C11 C10 49.1(6) . . . . ?
C9 C10 C11 O2 -25.4(5) . . . . ?
C4 C10 C11 O2 -156.1(4) . . . . ?
C9 C10 C11 C1 96.1(5) . . . . ?
C4 C10 C11 C1 -34.6(6) . . . . ?
C8 C9 N1 O2 -174.1(5) . . . . ?
C10 C9 N1 O2 -2.5(6) . . . . ?
C1 C11 O2 N1 -96.1(6) . . . . ?
C10 C11 O2 N1 26.1(5) . . . . ?
C9 N1 O2 C11 -15.6(6) . . . . ?
O4 C12 O3 C5 66.1(5) . . . . ?
C6 C5 O3 C12 69.7(5) . . . . ?
C4 C5 O3 C12 -167.4(3) . . . . ?
O3 C12 O4 C13 67.2(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.068
