# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_2014507_0m
_database_code_depnum_ccdc_archive 'CCDC 1046766'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.	2022-06-14 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 O4'
_chemical_formula_weight         249.26


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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0946(6)
_cell_length_b                   9.7401(7)
_cell_length_c                   10.3943(8)
_cell_angle_alpha                62.776(5)
_cell_angle_beta                 77.724(5)
_cell_angle_gamma                74.122(6)
_cell_volume                     611.11(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            9968
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0730
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.56
_reflns_number_total             2837
_reflns_number_gt                1251
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0828P)²+0.0000P] 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_number_reflns         2782
_refine_ls_number_parameters     173
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1456
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1715
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_refine_ls_shift/su_max          0.005
_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
H1S H 0.898(7) 0.115(6) 0.354(4) 0.16(2) Uiso 1 1 d D . .
O1S O 0.9449(6) 0.0968(3) 0.2785(3) 0.0975(9) Uani 1 1 d D . .
O1 O 0.5788(3) 0.30963(19) 0.85991(17) 0.0512(5) Uani 1 1 d . . .
O2 O 0.6947(3) 0.1204(2) 0.7829(2) 0.0724(7) Uani 1 1 d . . .
O3 O 0.8585(3) 0.2270(2) 0.49183(19) 0.0675(6) Uani 1 1 d . . .
N1 N 0.6897(3) 0.6656(2) 0.4850(2) 0.0434(6) Uani 1 1 d . . .
C4 C 0.9296(4) 0.7629(3) 0.1138(3) 0.0559(8) Uani 1 1 d . . .
H3 H 0.9566 0.8508 0.0300 0.067 Uiso 1 1 calc R . .
C5 C 0.8345(4) 0.7816(3) 0.2352(3) 0.0515(7) Uani 1 1 d . . .
H4 H 0.8000 0.8810 0.2348 0.062 Uiso 1 1 calc R . .
C6 C 0.7891(4) 0.6503(3) 0.3602(2) 0.0410(6) Uani 1 1 d . . .
C1 C 0.8478(3) 0.4999(3) 0.3620(2) 0.0396(6) Uani 1 1 d . . .
C9 C 0.8072(4) 0.3590(3) 0.4927(3) 0.0434(6) Uani 1 1 d . . .
C8 C 0.7084(3) 0.3867(3) 0.6167(2) 0.0394(6) Uani 1 1 d . . .
C11 C 0.6617(4) 0.2574(3) 0.7582(3) 0.0450(7) Uani 1 1 d . . .
C12 C 0.5358(5) 0.1913(3) 1.0051(3) 0.0604(8) Uani 1 1 d . . .
H9 H 0.6548 0.1136 1.0388 0.072 Uiso 1 1 calc R . .
H10 H 0.4396 0.1377 1.0042 0.072 Uiso 1 1 calc R . .
C13 C 0.4578(6) 0.2703(4) 1.1026(3) 0.0871(12) Uani 1 1 d . . .
H12 H 0.5597 0.3111 1.1130 0.131 Uiso 1 1 calc R . .
H11 H 0.4130 0.1959 1.1962 0.131 Uiso 1 1 calc R . .
H13 H 0.3497 0.3554 1.0623 0.131 Uiso 1 1 calc R . .
C10 C 0.6152(5) 0.8237(3) 0.4841(3) 0.0633(9) Uani 1 1 d . . .
H7 H 0.5508 0.8129 0.5784 0.095 Uiso 1 1 calc R . .
H6 H 0.5231 0.8853 0.4127 0.095 Uiso 1 1 calc R . .
H5 H 0.7234 0.8754 0.4605 0.095 Uiso 1 1 calc R . .
C7 C 0.6541(4) 0.5379(3) 0.6046(2) 0.0417(6) Uani 1 1 d . . .
H8 H 0.5872 0.5527 0.6859 0.050 Uiso 1 1 calc R . .
C3 C 0.9861(4) 0.6165(3) 0.1131(3) 0.0563(8) Uani 1 1 d . . .
H2 H 1.0510 0.6061 0.0293 0.068 Uiso 1 1 calc R . .
C2 C 0.9471(4) 0.4863(3) 0.2353(3) 0.0499(7) Uani 1 1 d . . .
H1 H 0.9869 0.3875 0.2344 0.060 Uiso 1 1 calc R . .
H2S H 1.069(4) 0.089(11) 0.283(10) 0.35(5) Uiso 1 1 d 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
O1S H1S 0.856(19) . ?
O1S H2S 0.87(2) . ?
O1 C11 1.337(3) . ?
O1 C12 1.450(3) . ?
O2 C11 1.201(3) . ?
O3 C9 1.240(3) . ?
N1 C7 1.334(3) . ?
N1 C6 1.391(3) . ?
N1 C10 1.481(3) . ?
C4 C5 1.364(3) . ?
C4 C3 1.375(3) . ?
C4 H3 0.9300 . ?
C5 C6 1.398(3) . ?
C5 H4 0.9300 . ?
C6 C1 1.401(3) . ?
C1 C2 1.401(3) . ?
C1 C9 1.469(3) . ?
C9 C8 1.434(3) . ?
C8 C7 1.368(3) . ?
C8 C11 1.479(3) . ?
C12 C13 1.473(4) . ?
C12 H9 0.9700 . ?
C12 H10 0.9700 . ?
C13 H12 0.9600 . ?
C13 H11 0.9600 . ?
C13 H13 0.9600 . ?
C10 H7 0.9600 . ?
C10 H6 0.9600 . ?
C10 H5 0.9600 . ?
C7 H8 0.9300 . ?
C3 C2 1.367(3) . ?
C3 H2 0.9300 . ?
C2 H1 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
H1S O1S H2S 98(6) . . ?
C11 O1 C12 116.57(19) . . ?
C7 N1 C6 119.88(19) . . ?
C7 N1 C10 119.7(2) . . ?
C6 N1 C10 120.35(19) . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H3 119.4 . . ?
C3 C4 H3 119.4 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H4 120.2 . . ?
C6 C5 H4 120.2 . . ?
N1 C6 C5 121.0(2) . . ?
N1 C6 C1 119.0(2) . . ?
C5 C6 C1 120.0(2) . . ?
C2 C1 C6 118.4(2) . . ?
C2 C1 C9 120.2(2) . . ?
C6 C1 C9 121.4(2) . . ?
O3 C9 C8 124.2(2) . . ?
O3 C9 C1 120.5(2) . . ?
C8 C9 C1 115.3(2) . . ?
C7 C8 C9 119.3(2) . . ?
C7 C8 C11 118.4(2) . . ?
C9 C8 C11 122.3(2) . . ?
O2 C11 O1 122.6(2) . . ?
O2 C11 C8 125.5(2) . . ?
O1 C11 C8 112.0(2) . . ?
O1 C12 C13 108.4(2) . . ?
O1 C12 H9 110.0 . . ?
C13 C12 H9 110.0 . . ?
O1 C12 H10 110.0 . . ?
C13 C12 H10 110.0 . . ?
H9 C12 H10 108.4 . . ?
C12 C13 H12 109.5 . . ?
C12 C13 H11 109.5 . . ?
H12 C13 H11 109.5 . . ?
C12 C13 H13 109.5 . . ?
H12 C13 H13 109.5 . . ?
H11 C13 H13 109.5 . . ?
N1 C10 H7 109.5 . . ?
N1 C10 H6 109.5 . . ?
H7 C10 H6 109.5 . . ?
N1 C10 H5 109.5 . . ?
H7 C10 H5 109.5 . . ?
H6 C10 H5 109.5 . . ?
N1 C7 C8 125.1(2) . . ?
N1 C7 H8 117.5 . . ?
C8 C7 H8 117.5 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H2 120.0 . . ?
C4 C3 H2 120.0 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H1 119.6 . . ?
C1 C2 H1 119.6 . . ?

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
C3 C4 C5 C6 -1.6(4) . . . . ?
C7 N1 C6 C5 -177.7(2) . . . . ?
C10 N1 C6 C5 5.1(4) . . . . ?
C7 N1 C6 C1 0.9(4) . . . . ?
C10 N1 C6 C1 -176.3(2) . . . . ?
C4 C5 C6 N1 -179.1(2) . . . . ?
C4 C5 C6 C1 2.4(4) . . . . ?
N1 C6 C1 C2 179.8(2) . . . . ?
C5 C6 C1 C2 -1.7(4) . . . . ?
N1 C6 C1 C9 -0.2(4) . . . . ?
C5 C6 C1 C9 178.3(2) . . . . ?
C2 C1 C9 O3 -0.8(4) . . . . ?
C6 C1 C9 O3 179.2(3) . . . . ?
C2 C1 C9 C8 178.8(2) . . . . ?
C6 C1 C9 C8 -1.2(3) . . . . ?
O3 C9 C8 C7 -178.4(3) . . . . ?
C1 C9 C8 C7 2.1(3) . . . . ?
O3 C9 C8 C11 1.3(4) . . . . ?
C1 C9 C8 C11 -178.2(2) . . . . ?
C12 O1 C11 O2 2.1(4) . . . . ?
C12 O1 C11 C8 -177.0(2) . . . . ?
C7 C8 C11 O2 177.4(3) . . . . ?
C9 C8 C11 O2 -2.3(4) . . . . ?
C7 C8 C11 O1 -3.5(3) . . . . ?
C9 C8 C11 O1 176.8(2) . . . . ?
C11 O1 C12 C13 176.4(2) . . . . ?
C6 N1 C7 C8 0.1(4) . . . . ?
C10 N1 C7 C8 177.3(2) . . . . ?
C9 C8 C7 N1 -1.7(4) . . . . ?
C11 C8 C7 N1 178.6(2) . . . . ?
C5 C4 C3 C2 0.1(4) . . . . ?
C4 C3 C2 C1 0.6(4) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C9 C1 C2 C3 -179.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.041
