# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_vbchem293S
_database_code_depnum_ccdc_archive 'CCDC 1831821'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            vbchem293S
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 N2 O5'
_chemical_formula_sum            'C21 H20 N2 O5'
_chemical_formula_weight         380.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.809(11)
_cell_length_b                   12.652(16)
_cell_length_c                   16.37(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.413(13)
_cell_angle_gamma                90
_cell_volume                     1824(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2471
_cell_measurement_theta_min      2.489
_cell_measurement_theta_max      28.234

_exptl_crystal_description       vbchem293S
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  char
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38543
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.489
_diffrn_reflns_theta_max         28.234
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4428
_reflns_number_gt                2471
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.8738P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4428
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1956
_refine_ls_R_factor_gt           0.1141
_refine_ls_wR_factor_ref         0.3356
_refine_ls_wR_factor_gt          0.2736
_refine_ls_goodness_of_fit_ref   1.547
_refine_ls_restrained_S_all      1.547
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6215(4) 1.1762(3) -0.0520(2) 0.0878(11) Uani 1 1 d . . . . .
O5 O 1.0991(4) 0.2847(3) 0.2113(2) 0.0801(10) Uani 1 1 d . . . . .
O4 O 1.2692(6) 0.2452(3) 0.1226(3) 0.1161(17) Uani 1 1 d . . . . .
O3 O 1.4408(5) 0.4149(4) 0.1713(3) 0.0952(14) Uani 1 1 d . . . . .
H15 H 1.484(10) 0.412(7) 0.211(5) 0.143 Uiso 1 1 d . U . . .
O2 O 0.8739(4) 0.8432(3) 0.2033(2) 0.0761(10) Uani 1 1 d . . . . .
N1 N 0.9363(4) 0.7603(3) 0.0877(2) 0.0607(10) Uani 1 1 d . . . . .
H8 H 0.9232 0.7617 0.0354 0.073 Uiso 1 1 calc R U . . .
N2 N 1.0899(4) 0.6497(3) -0.0192(2) 0.0593(9) Uani 1 1 d . . . . .
C1 C 0.5215(7) 1.2486(5) -0.0156(4) 0.0938(18) Uani 1 1 d . . . . .
H3 H 0.4299 1.2127 -0.0012 0.141 Uiso 1 1 calc R U . . .
H1 H 0.4976 1.3044 -0.0535 0.141 Uiso 1 1 calc R U . . .
H2 H 0.5692 1.2778 0.0327 0.141 Uiso 1 1 calc R U . . .
C2 C 0.6748(5) 1.0938(4) -0.0051(3) 0.0640(12) Uani 1 1 d . . . . .
C3 C 0.6385(6) 1.0766(4) 0.0740(3) 0.0723(13) Uani 1 1 d . . . . .
H7 H 0.5705 1.1210 0.0998 0.087 Uiso 1 1 calc R U . . .
C4 C 0.7032(6) 0.9928(4) 0.1154(3) 0.0705(13) Uani 1 1 d . . . . .
H6 H 0.6788 0.9818 0.1697 0.085 Uiso 1 1 calc R U . . .
C5 C 0.8023(5) 0.9252(3) 0.0792(3) 0.0548(10) Uani 1 1 d . . . . .
C8 C 0.8735(5) 0.8401(4) 0.1282(3) 0.0582(11) Uani 1 1 d . . . . .
C9 C 1.0208(5) 0.6744(3) 0.1187(3) 0.0558(10) Uani 1 1 d . . . . .
C14 C 1.1035(4) 0.6168(3) 0.0593(2) 0.0498(10) Uani 1 1 d . . . . .
C13 C 1.1928(4) 0.5297(3) 0.0843(2) 0.0508(10) Uani 1 1 d . . . . .
C12 C 1.1988(5) 0.5009(4) 0.1672(3) 0.0577(11) Uani 1 1 d . . . . .
C18 C 1.2929(5) 0.4076(4) 0.1975(3) 0.0680(13) Uani 1 1 d . . . . .
H14 H 1.2960 0.4098 0.2574 0.082 Uiso 1 1 calc R U . . .
C19 C 1.2212(6) 0.3035(4) 0.1716(3) 0.0698(13) Uani 1 1 d . . . . .
C20 C 1.0179(7) 0.1856(4) 0.1942(3) 0.0849(16) Uani 1 1 d . . . . .
H17 H 0.9576 0.1920 0.1441 0.102 Uiso 1 1 calc R U . . .
H16 H 1.0898 0.1283 0.1878 0.102 Uiso 1 1 calc R U . . .
C21 C 0.9219(10) 0.1643(6) 0.2613(4) 0.128(3) Uani 1 1 d . . . . .
H20 H 0.9830 0.1546 0.3101 0.192 Uiso 1 1 calc R U . . .
H19 H 0.8642 0.1013 0.2503 0.192 Uiso 1 1 calc R U . . .
H18 H 0.8539 0.2227 0.2686 0.192 Uiso 1 1 calc R U . . .
C15 C 1.1660(5) 0.5971(4) -0.0735(3) 0.0657(12) Uani 1 1 d . . . . .
H13 H 1.1581 0.6185 -0.1277 0.079 Uiso 1 1 calc R U . . .
C16 C 1.2580(5) 0.5107(4) -0.0542(3) 0.0660(13) Uani 1 1 d . . . . .
H12 H 1.3100 0.4762 -0.0951 0.079 Uiso 1 1 calc R U . . .
C17 C 1.2716(5) 0.4776(4) 0.0229(3) 0.0612(11) Uani 1 1 d . . . . .
H11 H 1.3333 0.4200 0.0359 0.073 Uiso 1 1 calc R U . . .
C7 C 0.7730(6) 1.0274(4) -0.0423(3) 0.0761(14) Uani 1 1 d . . . . .
H4 H 0.7982 1.0394 -0.0964 0.091 Uiso 1 1 calc R U . . .
C6 C 0.8353(6) 0.9429(4) -0.0011(3) 0.0699(13) Uani 1 1 d . . . . .
H5 H 0.9003 0.8973 -0.0278 0.084 Uiso 1 1 calc R U . . .
C10 C 1.0274(5) 0.6442(4) 0.1977(3) 0.0635(12) Uani 1 1 d . . . . .
H9 H 0.9730 0.6807 0.2366 0.076 Uiso 1 1 calc R U . . .
C11 C 1.1174(6) 0.5569(4) 0.2204(3) 0.0686(12) Uani 1 1 d . . . . .
H10 H 1.1210 0.5369 0.2751 0.082 Uiso 1 1 calc R U . . .


_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 C2 1.371(6) . ?
O1 C1 1.412(7) . ?
O5 C19 1.293(6) . ?
O5 C20 1.467(7) . ?
O4 C19 1.177(6) . ?
O3 C18 1.385(6) . ?
O3 H15 0.74(8) . ?
O2 C8 1.230(5) . ?
N1 C8 1.336(5) . ?
N1 C9 1.405(6) . ?
N1 H8 0.8600 . ?
N2 C15 1.308(6) . ?
N2 C14 1.354(5) . ?
C1 H3 0.9600 . ?
C1 H1 0.9600 . ?
C1 H2 0.9600 . ?
C2 C3 1.358(7) . ?
C2 C7 1.361(7) . ?
C3 C4 1.375(7) . ?
C3 H7 0.9300 . ?
C4 C5 1.368(6) . ?
C4 H6 0.9300 . ?
C5 C6 1.372(7) . ?
C5 C8 1.473(7) . ?
C9 C10 1.349(6) . ?
C9 C14 1.428(6) . ?
C14 C13 1.409(6) . ?
C13 C17 1.401(6) . ?
C13 C12 1.404(6) . ?
C12 C11 1.345(6) . ?
C12 C18 1.519(7) . ?
C18 C19 1.516(8) . ?
C18 H14 0.9800 . ?
C20 C21 1.429(8) . ?
C20 H17 0.9700 . ?
C20 H16 0.9700 . ?
C21 H20 0.9600 . ?
C21 H19 0.9600 . ?
C21 H18 0.9600 . ?
C15 C16 1.392(7) . ?
C15 H13 0.9300 . ?
C16 C17 1.333(6) . ?
C16 H12 0.9300 . ?
C17 H11 0.9300 . ?
C7 C6 1.371(7) . ?
C7 H4 0.9300 . ?
C6 H5 0.9300 . ?
C10 C11 1.404(7) . ?
C10 H9 0.9300 . ?
C11 H10 0.9300 . ?

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
C2 O1 C1 117.7(4) . . ?
C19 O5 C20 118.0(4) . . ?
C18 O3 H15 101(7) . . ?
C8 N1 C9 128.8(4) . . ?
C8 N1 H8 115.6 . . ?
C9 N1 H8 115.6 . . ?
C15 N2 C14 117.0(4) . . ?
O1 C1 H3 109.5 . . ?
O1 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
O1 C1 H2 109.5 . . ?
H3 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
C3 C2 C7 119.7(5) . . ?
C3 C2 O1 124.8(5) . . ?
C7 C2 O1 115.6(4) . . ?
C2 C3 C4 119.3(5) . . ?
C2 C3 H7 120.4 . . ?
C4 C3 H7 120.4 . . ?
C5 C4 C3 122.0(5) . . ?
C5 C4 H6 119.0 . . ?
C3 C4 H6 119.0 . . ?
C4 C5 C6 117.7(4) . . ?
C4 C5 C8 119.2(4) . . ?
C6 C5 C8 123.0(4) . . ?
O2 C8 N1 122.0(4) . . ?
O2 C8 C5 120.8(4) . . ?
N1 C8 C5 117.2(4) . . ?
C10 C9 N1 125.2(4) . . ?
C10 C9 C14 119.8(4) . . ?
N1 C9 C14 115.1(4) . . ?
N2 C14 C13 123.5(4) . . ?
N2 C14 C9 117.0(4) . . ?
C13 C14 C9 119.5(4) . . ?
C17 C13 C12 124.3(4) . . ?
C17 C13 C14 116.3(4) . . ?
C12 C13 C14 119.4(4) . . ?
C11 C12 C13 118.8(4) . . ?
C11 C12 C18 119.5(4) . . ?
C13 C12 C18 121.7(4) . . ?
O3 C18 C19 111.1(4) . . ?
O3 C18 C12 110.9(4) . . ?
C19 C18 C12 111.3(4) . . ?
O3 C18 H14 107.8 . . ?
C19 C18 H14 107.8 . . ?
C12 C18 H14 107.8 . . ?
O4 C19 O5 123.0(5) . . ?
O4 C19 C18 125.5(5) . . ?
O5 C19 C18 111.5(4) . . ?
C21 C20 O5 108.0(5) . . ?
C21 C20 H17 110.1 . . ?
O5 C20 H17 110.1 . . ?
C21 C20 H16 110.1 . . ?
O5 C20 H16 110.1 . . ?
H17 C20 H16 108.4 . . ?
C20 C21 H20 109.5 . . ?
C20 C21 H19 109.5 . . ?
H20 C21 H19 109.5 . . ?
C20 C21 H18 109.5 . . ?
H20 C21 H18 109.5 . . ?
H19 C21 H18 109.5 . . ?
N2 C15 C16 123.4(4) . . ?
N2 C15 H13 118.3 . . ?
C16 C15 H13 118.3 . . ?
C17 C16 C15 120.0(4) . . ?
C17 C16 H12 120.0 . . ?
C15 C16 H12 120.0 . . ?
C16 C17 C13 119.8(4) . . ?
C16 C17 H11 120.1 . . ?
C13 C17 H11 120.1 . . ?
C2 C7 C6 120.8(5) . . ?
C2 C7 H4 119.6 . . ?
C6 C7 H4 119.6 . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H5 119.7 . . ?
C5 C6 H5 119.7 . . ?
C9 C10 C11 119.2(4) . . ?
C9 C10 H9 120.4 . . ?
C11 C10 H9 120.4 . . ?
C12 C11 C10 123.3(4) . . ?
C12 C11 H10 118.4 . . ?
C10 C11 H10 118.4 . . ?

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
C1 O1 C2 C3 0.1(7) . . . . ?
C1 O1 C2 C7 -178.7(5) . . . . ?
C7 C2 C3 C4 0.8(8) . . . . ?
O1 C2 C3 C4 -178.0(5) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
C3 C4 C5 C8 177.0(4) . . . . ?
C9 N1 C8 O2 -5.7(7) . . . . ?
C9 N1 C8 C5 174.6(4) . . . . ?
C4 C5 C8 O2 -17.0(6) . . . . ?
C6 C5 C8 O2 160.3(4) . . . . ?
C4 C5 C8 N1 162.8(4) . . . . ?
C6 C5 C8 N1 -19.9(6) . . . . ?
C8 N1 C9 C10 15.1(7) . . . . ?
C8 N1 C9 C14 -165.3(4) . . . . ?
C15 N2 C14 C13 -0.6(6) . . . . ?
C15 N2 C14 C9 179.8(4) . . . . ?
C10 C9 C14 N2 178.7(4) . . . . ?
N1 C9 C14 N2 -0.9(5) . . . . ?
C10 C9 C14 C13 -0.9(6) . . . . ?
N1 C9 C14 C13 179.5(3) . . . . ?
N2 C14 C13 C17 0.9(6) . . . . ?
C9 C14 C13 C17 -179.5(4) . . . . ?
N2 C14 C13 C12 -179.4(4) . . . . ?
C9 C14 C13 C12 0.1(5) . . . . ?
C17 C13 C12 C11 -179.7(4) . . . . ?
C14 C13 C12 C11 0.6(6) . . . . ?
C17 C13 C12 C18 -0.5(6) . . . . ?
C14 C13 C12 C18 179.8(4) . . . . ?
C11 C12 C18 O3 -129.0(5) . . . . ?
C13 C12 C18 O3 51.8(6) . . . . ?
C11 C12 C18 C19 106.9(5) . . . . ?
C13 C12 C18 C19 -72.3(5) . . . . ?
C20 O5 C19 O4 0.3(8) . . . . ?
C20 O5 C19 C18 -178.8(4) . . . . ?
O3 C18 C19 O4 -14.4(7) . . . . ?
C12 C18 C19 O4 109.6(6) . . . . ?
O3 C18 C19 O5 164.7(4) . . . . ?
C12 C18 C19 O5 -71.2(5) . . . . ?
C19 O5 C20 C21 160.6(6) . . . . ?
C14 N2 C15 C16 0.0(7) . . . . ?
N2 C15 C16 C17 0.2(7) . . . . ?
C15 C16 C17 C13 0.2(7) . . . . ?
C12 C13 C17 C16 179.7(4) . . . . ?
C14 C13 C17 C16 -0.7(6) . . . . ?
C3 C2 C7 C6 0.3(8) . . . . ?
O1 C2 C7 C6 179.2(4) . . . . ?
C2 C7 C6 C5 -1.5(8) . . . . ?
C4 C5 C6 C7 1.6(7) . . . . ?
C8 C5 C6 C7 -175.8(4) . . . . ?
N1 C9 C10 C11 -179.6(4) . . . . ?
C14 C9 C10 C11 0.8(6) . . . . ?
C13 C12 C11 C10 -0.8(7) . . . . ?
C18 C12 C11 C10 -180.0(4) . . . . ?
C9 C10 C11 C12 0.0(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H9 O2 0.93 2.29 2.861(7) 118.8 .
C21 H18 O2 0.96 2.57 3.510(10) 166.0 2_645
C1 H3 O4 0.96 2.53 3.210(8) 127.5 1_465
O3 H15 O2 0.74(8) 2.06(8) 2.746(5) 155(9) 2_745
C1 H2 O3 0.96 3.09 3.794(9) 131.3 1_465
C1 H2 O3 0.96 3.09 3.794(9) 131.3 1_465
C1 H2 O3 0.96 3.09 3.794(9) 131.3 1_465
O3 H15 O2 0.74(8) 2.06(8) 2.746(5) 155(9) 2_745
C1 H3 O4 0.96 2.53 3.210(8) 127.5 1_465
C21 H18 O2 0.96 2.57 3.510(10) 166.0 2_645
C10 H9 O2 0.93 2.29 2.861(7) 118.8 .

_refine_diff_density_max         0.514
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.167

