# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_24ME_DMDE_SA_ATK_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2053801'
_audit_update_record             
;
2021-01-04 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N O4'
_chemical_formula_weight         273.28

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                   3.9964(3)
_cell_length_b                   38.647(3)
_cell_length_c                   8.7063(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.942(3)
_cell_angle_gamma                90
_cell_volume                     1331.77(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5731
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      28.15

_exptl_crystal_description       Needle
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   0.908
_exptl_transmission_factor_max   0.942
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.6
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   multi-scan
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18621
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.108
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3314
_reflns_number_gt                2419
_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+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3314
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.2032
_refine_ls_wR_factor_gt          0.1844
_refine_ls_goodness_of_fit_ref   1.262
_refine_ls_restrained_S_all      1.262
_refine_ls_shift/su_max          0.004
_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_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
O4 O 0.6330(4) 0.54003(3) 0.44549(16) 0.0514(4) Uani 1 1 d . . . . .
O2 O 0.8402(5) 0.69790(4) 0.48241(17) 0.0644(5) Uani 1 1 d . . . . .
N1 N 0.4960(4) 0.58447(4) 0.66377(16) 0.0370(4) Uani 1 1 d . . . . .
O3 O 0.8526(5) 0.58189(4) 0.31604(17) 0.0688(5) Uani 1 1 d . . . . .
O1 O 0.6849(6) 0.71593(4) 0.7000(2) 0.0894(7) Uani 1 1 d . . . . .
C9 C 0.6312(4) 0.59697(4) 0.54582(19) 0.0359(4) Uani 1 1 d . . . . .
C3 C 0.4986(4) 0.64350(5) 0.76953(19) 0.0360(4) Uani 1 1 d . . . . .
C7 C 0.6414(4) 0.65540(4) 0.63729(19) 0.0361(4) Uani 1 1 d . . . . .
C8 C 0.7058(5) 0.63203(4) 0.52752(19) 0.0379(4) Uani 1 1 d . . . . .
H8 H 0.7989 0.6394 0.4409 0.045 Uiso 1 1 calc R U . . .
C14 C 0.7202(5) 0.69294(5) 0.6146(2) 0.0426(4) Uani 1 1 d . . . . .
C12 C 0.7183(5) 0.57259(5) 0.4232(2) 0.0407(4) Uani 1 1 d . . . . .
C4 C 0.4301(4) 0.60719(5) 0.77581(19) 0.0359(4) Uani 1 1 d . . . . .
C2 C 0.4225(5) 0.66471(5) 0.8920(2) 0.0419(4) Uani 1 1 d . . . . .
H2 H 0.4641 0.6884 0.8889 0.050 Uiso 1 1 calc R U . . .
C5 C 0.2875(5) 0.59342(5) 0.9045(2) 0.0410(4) Uani 1 1 d . . . . .
C1 C 0.2884(5) 0.65109(6) 1.0153(2) 0.0453(5) Uani 1 1 d . . . . .
C13 C 0.7122(7) 0.51577(5) 0.3300(3) 0.0585(6) Uani 1 1 d . . . . .
H13A H 0.6095 0.5233 0.2293 0.088 Uiso 1 1 calc R U . . .
H13B H 0.6272 0.4933 0.3516 0.088 Uiso 1 1 calc R U . . .
H13C H 0.9528 0.5146 0.3322 0.088 Uiso 1 1 calc R U . . .
C11 C 0.2118(6) 0.55545(5) 0.9112(2) 0.0548(5) Uani 1 1 d . . . . .
H11A H 0.1126 0.5506 1.0031 0.082 Uiso 1 1 calc R U . . .
H11B H 0.4174 0.5425 0.9132 0.082 Uiso 1 1 calc R U . . .
H11C H 0.0570 0.5490 0.8214 0.082 Uiso 1 1 calc R U . . .
C6 C 0.2232(5) 0.61529(6) 1.0196(2) 0.0471(5) Uani 1 1 d . . . . .
H6 H 0.1330 0.6063 1.1040 0.057 Uiso 1 1 calc R U . . .
C10 C 0.2094(6) 0.67384(6) 1.1458(2) 0.0613(6) Uani 1 1 d . . . . .
H10A H 0.3105 0.6962 1.1374 0.092 Uiso 1 1 calc R U . . .
H10B H 0.2983 0.6635 1.2432 0.092 Uiso 1 1 calc R U . . .
H10C H -0.0310 0.6764 1.1401 0.092 Uiso 1 1 calc R U . . .
C15 C 0.9155(8) 0.73308(5) 0.4441(3) 0.0695(7) Uani 1 1 d . . . . .
H15A H 0.7094 0.7461 0.4249 0.104 Uiso 1 1 calc R U . . .
H15B H 1.0262 0.7333 0.3531 0.104 Uiso 1 1 calc R U . . .
H15C H 1.0611 0.7433 0.5290 0.104 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
O4 C12 1.325(2) . ?
O4 C13 1.441(2) . ?
O2 C14 1.321(2) . ?
O2 C15 1.441(2) . ?
N1 C9 1.316(2) . ?
N1 C4 1.365(2) . ?
O3 C12 1.194(2) . ?
O1 C14 1.179(2) . ?
C9 C8 1.401(2) . ?
C9 C12 1.501(2) . ?
C3 C2 1.411(2) . ?
C3 C7 1.430(2) . ?
C3 C4 1.432(3) . ?
C7 C8 1.365(2) . ?
C7 C14 1.503(2) . ?
C8 H8 0.9300 . ?
C4 C5 1.428(2) . ?
C2 C1 1.370(3) . ?
C2 H2 0.9300 . ?
C5 C6 1.362(3) . ?
C5 C11 1.501(3) . ?
C1 C6 1.409(3) . ?
C1 C10 1.504(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C6 H6 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C12 O4 C13 115.44(14) . . ?
C14 O2 C15 116.80(17) . . ?
C9 N1 C4 117.52(15) . . ?
N1 C9 C8 124.08(16) . . ?
N1 C9 C12 119.04(15) . . ?
C8 C9 C12 116.88(15) . . ?
C2 C3 C7 124.97(16) . . ?
C2 C3 C4 118.57(16) . . ?
C7 C3 C4 116.47(15) . . ?
C8 C7 C3 119.06(16) . . ?
C8 C7 C14 118.91(15) . . ?
C3 C7 C14 122.04(15) . . ?
C7 C8 C9 119.76(15) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
O1 C14 O2 121.97(18) . . ?
O1 C14 C7 126.78(18) . . ?
O2 C14 C7 111.24(15) . . ?
O3 C12 O4 123.58(17) . . ?
O3 C12 C9 122.71(17) . . ?
O4 C12 C9 113.71(15) . . ?
N1 C4 C5 117.28(16) . . ?
N1 C4 C3 123.11(15) . . ?
C5 C4 C3 119.61(16) . . ?
C1 C2 C3 121.17(18) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C6 C5 C4 118.83(18) . . ?
C6 C5 C11 121.23(17) . . ?
C4 C5 C11 119.94(17) . . ?
C2 C1 C6 119.45(17) . . ?
C2 C1 C10 120.87(19) . . ?
C6 C1 C10 119.68(18) . . ?
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 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C6 C1 122.37(17) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.112

