# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_mtk120n
_database_code_depnum_ccdc_archive 'CCDC 2211404'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universitaet zu Koeln
Germany
;
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H23 N O6'
_chemical_formula_sum            'C14 H23 N O6'
_chemical_formula_weight         301.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.0019(3)
_cell_length_b                   10.5127(4)
_cell_length_c                   17.2834(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1453.91(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    24294
_cell_measurement_theta_min      4.924
_cell_measurement_theta_max      71.96
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.900
_shelx_estimated_absorpt_T_min   0.841
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5505
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_detector_type            'Bruker Photon 100'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24294
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.924
_diffrn_reflns_theta_max         71.961
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2851
_reflns_number_gt                2825
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        
;
Bruker APEX 3
SADABS Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'

_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)+(0.0333P)²+0.3598P] 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_abs_structure_details 
;
 Flack x determined using 1179 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2851
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0646
_refine_ls_wR_factor_gt          0.0644
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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_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 0.30951(13) 0.46138(10) 0.11183(6) 0.0122(2) Uani 1 1 d . . . . .
O2 O 0.44757(14) 0.61152(11) 0.18369(6) 0.0161(2) Uani 1 1 d . . . . .
O3 O -0.05643(14) 0.55284(11) -0.01022(6) 0.0169(2) Uani 1 1 d . . . . .
O4 O 0.15707(15) 0.68831(11) 0.01134(7) 0.0187(3) Uani 1 1 d . . . . .
O5 O -0.28376(16) 0.68633(13) 0.27275(7) 0.0224(3) Uani 1 1 d . . . . .
H23 H -0.372(4) 0.662(2) 0.2482(15) 0.038(7) Uiso 1 1 d . . . . .
O6 O -0.01775(15) 0.76951(11) 0.33807(7) 0.0186(3) Uani 1 1 d . . . . .
H20 H -0.124(4) 0.783(3) 0.3347(16) 0.048(8) Uiso 1 1 d . . . . .
N1 N 0.16532(16) 0.61477(12) 0.16749(8) 0.0127(3) Uani 1 1 d . . . . .
C1 C 0.31937(19) 0.56683(14) 0.15625(9) 0.0111(3) Uani 1 1 d . . . . .
C2 C 0.01978(18) 0.58361(13) 0.11923(9) 0.0116(3) Uani 1 1 d . . . . .
H5 H -0.014518 0.492800 0.125933 0.014 Uiso 1 1 calc R U . . .
C3 C 0.05226(19) 0.61503(15) 0.03432(9) 0.0131(3) Uani 1 1 d . . . . .
C4 C -0.0556(2) 0.58650(18) -0.09205(9) 0.0215(4) Uani 1 1 d . . . . .
H11 H -0.045838 0.680000 -0.097211 0.026 Uiso 1 1 calc R U . . .
H18 H -0.162851 0.560289 -0.115697 0.026 Uiso 1 1 calc R U . . .
C5 C 0.0852(2) 0.52457(18) -0.13466(10) 0.0251(4) Uani 1 1 d . . . . .
H17 H 0.191874 0.553556 -0.113080 0.038 Uiso 1 1 calc R U . . .
H21 H 0.079350 0.547552 -0.189540 0.038 Uiso 1 1 calc R U . . .
H22 H 0.076687 0.431994 -0.129278 0.038 Uiso 1 1 calc R U . . .
C6 C -0.11007(19) 0.67518(14) 0.15473(9) 0.0127(3) Uani 1 1 d . . . . .
H2 H -0.212601 0.688845 0.122711 0.015 Uiso 1 1 calc R U . . .
C7 C -0.14301(19) 0.62769(15) 0.23812(9) 0.0147(3) Uani 1 1 d . . . . .
H1 H -0.153752 0.532936 0.239363 0.018 Uiso 1 1 calc R U . . .
C8 C 0.0174(2) 0.67236(15) 0.28357(9) 0.0136(3) Uani 1 1 d . . . . .
H8 H 0.073280 0.598469 0.309213 0.016 Uiso 1 1 calc R U . . .
C9 C 0.12618(19) 0.72467(14) 0.21745(9) 0.0127(3) Uani 1 1 d . . . . .
H7 H 0.224561 0.776607 0.234031 0.015 Uiso 1 1 calc R U . . .
C10 C -0.00379(19) 0.79525(14) 0.16871(9) 0.0146(3) Uani 1 1 d . . . . .
H4 H 0.043254 0.831200 0.120454 0.018 Uiso 1 1 calc R U . . .
H9 H -0.064023 0.861768 0.198144 0.018 Uiso 1 1 calc R U . . .
C11 C 0.45835(19) 0.40646(14) 0.07303(8) 0.0127(3) Uani 1 1 d . . . . .
C12 C 0.3840(2) 0.29263(16) 0.03100(10) 0.0181(3) Uani 1 1 d . . . . .
H12 H 0.292545 0.321183 -0.002505 0.027 Uiso 1 1 calc R U . . .
H15 H 0.340878 0.231585 0.068929 0.027 Uiso 1 1 calc R U . . .
H19 H 0.470502 0.251793 -0.000504 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5881(2) 0.36440(15) 0.13206(10) 0.0162(3) Uani 1 1 d . . . . .
H3 H 0.636565 0.439390 0.157178 0.024 Uiso 1 1 calc R U . . .
H6 H 0.676546 0.316341 0.105902 0.024 Uiso 1 1 calc R U . . .
H10 H 0.534791 0.310366 0.171118 0.024 Uiso 1 1 calc R U . . .
C14 C 0.5265(2) 0.50332(16) 0.01598(10) 0.0205(4) Uani 1 1 d . . . . .
H13 H 0.617937 0.465117 -0.013713 0.031 Uiso 1 1 calc R U . . .
H14 H 0.568186 0.577640 0.044240 0.031 Uiso 1 1 calc R U . . .
H16 H 0.437250 0.529704 -0.019388 0.031 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 C1 1.3507(18) . ?
O1 C11 1.4838(17) . ?
O2 C1 1.2240(19) . ?
O3 C3 1.3328(19) . ?
O3 C4 1.4579(19) . ?
O4 C3 1.206(2) . ?
O5 C7 1.417(2) . ?
O5 H23 0.86(3) . ?
O6 C8 1.4176(18) . ?
O6 H20 0.86(3) . ?
N1 C1 1.346(2) . ?
N1 C2 1.4694(19) . ?
N1 C9 1.4760(19) . ?
C2 C3 1.527(2) . ?
C2 C6 1.544(2) . ?
C2 H5 1.0000 . ?
C4 C5 1.495(3) . ?
C4 H11 0.9900 . ?
C4 H18 0.9900 . ?
C5 H17 0.9800 . ?
C5 H21 0.9800 . ?
C5 H22 0.9800 . ?
C6 C10 1.541(2) . ?
C6 C7 1.548(2) . ?
C6 H2 1.0000 . ?
C7 C8 1.576(2) . ?
C7 H1 1.0000 . ?
C8 C9 1.538(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.530(2) . ?
C9 H7 1.0000 . ?
C10 H4 0.9900 . ?
C10 H9 0.9900 . ?
C11 C14 1.519(2) . ?
C11 C12 1.521(2) . ?
C11 C13 1.521(2) . ?
C12 H12 0.9800 . ?
C12 H15 0.9800 . ?
C12 H19 0.9800 . ?
C13 H3 0.9800 . ?
C13 H6 0.9800 . ?
C13 H10 0.9800 . ?
C14 H13 0.9800 . ?
C14 H14 0.9800 . ?
C14 H16 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 O1 C11 121.96(11) . . ?
C3 O3 C4 115.98(13) . . ?
C7 O5 H23 108.4(17) . . ?
C8 O6 H20 105.7(19) . . ?
C1 N1 C2 124.09(13) . . ?
C1 N1 C9 124.89(13) . . ?
C2 N1 C9 109.78(12) . . ?
O2 C1 N1 124.61(14) . . ?
O2 C1 O1 125.74(13) . . ?
N1 C1 O1 109.63(12) . . ?
N1 C2 C3 111.25(12) . . ?
N1 C2 C6 99.72(11) . . ?
C3 C2 C6 111.21(12) . . ?
N1 C2 H5 111.4 . . ?
C3 C2 H5 111.4 . . ?
C6 C2 H5 111.4 . . ?
O4 C3 O3 125.24(15) . . ?
O4 C3 C2 124.97(14) . . ?
O3 C3 C2 109.75(13) . . ?
O3 C4 C5 112.07(14) . . ?
O3 C4 H11 109.2 . . ?
C5 C4 H11 109.2 . . ?
O3 C4 H18 109.2 . . ?
C5 C4 H18 109.2 . . ?
H11 C4 H18 107.9 . . ?
C4 C5 H17 109.5 . . ?
C4 C5 H21 109.5 . . ?
H17 C5 H21 109.5 . . ?
C4 C5 H22 109.5 . . ?
H17 C5 H22 109.5 . . ?
H21 C5 H22 109.5 . . ?
C10 C6 C2 101.64(12) . . ?
C10 C6 C7 102.25(12) . . ?
C2 C6 C7 106.47(12) . . ?
C10 C6 H2 115.0 . . ?
C2 C6 H2 115.0 . . ?
C7 C6 H2 115.0 . . ?
O5 C7 C6 112.85(13) . . ?
O5 C7 C8 107.88(12) . . ?
C6 C7 C8 103.25(12) . . ?
O5 C7 H1 110.9 . . ?
C6 C7 H1 110.9 . . ?
C8 C7 H1 110.9 . . ?
O6 C8 C9 110.38(12) . . ?
O6 C8 C7 112.61(13) . . ?
C9 C8 C7 101.37(12) . . ?
O6 C8 H8 110.7 . . ?
C9 C8 H8 110.7 . . ?
C7 C8 H8 110.7 . . ?
N1 C9 C10 101.63(12) . . ?
N1 C9 C8 105.96(12) . . ?
C10 C9 C8 101.40(12) . . ?
N1 C9 H7 115.3 . . ?
C10 C9 H7 115.3 . . ?
C8 C9 H7 115.3 . . ?
C9 C10 C6 93.68(12) . . ?
C9 C10 H4 113.0 . . ?
C6 C10 H4 113.0 . . ?
C9 C10 H9 113.0 . . ?
C6 C10 H9 113.0 . . ?
H4 C10 H9 110.4 . . ?
O1 C11 C14 108.70(12) . . ?
O1 C11 C12 101.99(12) . . ?
C14 C11 C12 110.97(13) . . ?
O1 C11 C13 110.97(11) . . ?
C14 C11 C13 112.66(13) . . ?
C12 C11 C13 111.02(13) . . ?
C11 C12 H12 109.5 . . ?
C11 C12 H15 109.5 . . ?
H12 C12 H15 109.5 . . ?
C11 C12 H19 109.5 . . ?
H12 C12 H19 109.5 . . ?
H15 C12 H19 109.5 . . ?
C11 C13 H3 109.5 . . ?
C11 C13 H6 109.5 . . ?
H3 C13 H6 109.5 . . ?
C11 C13 H10 109.5 . . ?
H3 C13 H10 109.5 . . ?
H6 C13 H10 109.5 . . ?
C11 C14 H13 109.5 . . ?
C11 C14 H14 109.5 . . ?
H13 C14 H14 109.5 . . ?
C11 C14 H16 109.5 . . ?
H13 C14 H16 109.5 . . ?
H14 C14 H16 109.5 . . ?

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
C2 N1 C1 O2 162.89(14) . . . . ?
C9 N1 C1 O2 -3.0(2) . . . . ?
C2 N1 C1 O1 -18.4(2) . . . . ?
C9 N1 C1 O1 175.65(13) . . . . ?
C11 O1 C1 O2 -17.3(2) . . . . ?
C11 O1 C1 N1 164.06(12) . . . . ?
C1 N1 C2 C3 -57.31(18) . . . . ?
C9 N1 C2 C3 110.46(14) . . . . ?
C1 N1 C2 C6 -174.72(13) . . . . ?
C9 N1 C2 C6 -6.95(15) . . . . ?
C4 O3 C3 O4 -5.8(2) . . . . ?
C4 O3 C3 C2 172.03(13) . . . . ?
N1 C2 C3 O4 -20.7(2) . . . . ?
C6 C2 C3 O4 89.49(18) . . . . ?
N1 C2 C3 O3 161.51(12) . . . . ?
C6 C2 C3 O3 -88.30(15) . . . . ?
C3 O3 C4 C5 79.06(18) . . . . ?
N1 C2 C6 C10 39.68(14) . . . . ?
C3 C2 C6 C10 -77.77(14) . . . . ?
N1 C2 C6 C7 -66.99(14) . . . . ?
C3 C2 C6 C7 175.56(12) . . . . ?
C10 C6 C7 O5 85.77(15) . . . . ?
C2 C6 C7 O5 -168.00(12) . . . . ?
C10 C6 C7 C8 -30.44(14) . . . . ?
C2 C6 C7 C8 75.79(13) . . . . ?
O5 C7 C8 O6 -8.01(17) . . . . ?
C6 C7 C8 O6 111.68(14) . . . . ?
O5 C7 C8 C9 -125.95(13) . . . . ?
C6 C7 C8 C9 -6.26(14) . . . . ?
C1 N1 C9 C10 139.31(15) . . . . ?
C2 N1 C9 C10 -28.34(15) . . . . ?
C1 N1 C9 C8 -115.10(16) . . . . ?
C2 N1 C9 C8 77.25(15) . . . . ?
O6 C8 C9 N1 175.99(12) . . . . ?
C7 C8 C9 N1 -64.47(14) . . . . ?
O6 C8 C9 C10 -78.25(14) . . . . ?
C7 C8 C9 C10 41.29(14) . . . . ?
N1 C9 C10 C6 49.97(13) . . . . ?
C8 C9 C10 C6 -59.17(13) . . . . ?
C2 C6 C10 C9 -55.47(13) . . . . ?
C7 C6 C10 C9 54.46(13) . . . . ?
C1 O1 C11 C14 -62.42(17) . . . . ?
C1 O1 C11 C12 -179.69(13) . . . . ?
C1 O1 C11 C13 62.01(17) . . . . ?

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.041

