# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Z_215_0m
_database_code_depnum_ccdc_archive 'CCDC 1975296'
loop_
_audit_author_name
_audit_author_address
'Maja Morawiak'
;Institute of Organic Chemistry Polish Academy of Science
Poland
;
_audit_update_record             
;
2020-01-03 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 N O6'
_chemical_formula_sum            'C18 H21 N O6'
_chemical_formula_weight         347.36

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

_cell_length_a                   5.7158(8)
_cell_length_b                   16.615(2)
_cell_length_c                   19.036(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1807.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2566
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      68.42

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.558
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.803
_shelx_estimated_absorpt_T_min   0.663
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6630
_exptl_absorpt_correction_T_max  0.9460
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14421
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.531
_diffrn_reflns_theta_max         68.416
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3302
_reflns_number_gt                2566
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.708
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.1660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3302
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.4694(4) 0.81096(15) 1.01915(13) 0.0744(7) Uani 1 1 d . . . . .
O2 O 1.0413(5) 0.97636(15) 1.11320(12) 0.0758(7) Uani 1 1 d . . . . .
O3 O 1.0953(4) 0.99169(12) 0.87986(11) 0.0581(6) Uani 1 1 d . . . . .
O4 O 0.8169(6) 1.07379(19) 0.83895(16) 0.0911(9) Uani 1 1 d . . . . .
O5 O 1.2154(4) 1.10626(13) 0.96570(13) 0.0638(6) Uani 1 1 d . . . . .
O6 O 1.5730(5) 1.11264(16) 1.01243(14) 0.0771(7) Uani 1 1 d . . . . .
N1 N 0.7250(4) 0.87039(16) 0.93916(13) 0.0527(6) Uani 1 1 d . . . . .
C1 C 0.6509(6) 0.84374(19) 1.00199(18) 0.0556(8) Uani 1 1 d . . . . .
C2 C 0.8704(6) 0.87328(19) 1.03901(17) 0.0565(8) Uani 1 1 d . . . . .
C3 C 0.9502(6) 0.90103(18) 0.96477(16) 0.0494(7) Uani 1 1 d . . . . .
C4 C 0.9939(6) 0.98878(18) 0.94986(15) 0.0491(7) Uani 1 1 d . . . . .
C5 C 1.1725(6) 1.02871(18) 0.99769(18) 0.0552(8) Uani 1 1 d . . . . .
C6 C 1.0882(7) 1.0459(2) 1.07237(18) 0.0650(9) Uani 1 1 d . . . . .
H6A H 1.2061 1.0777 1.0963 0.078 Uiso 1 1 calc R U . . .
H6B H 0.9469 1.0780 1.0698 0.078 Uiso 1 1 calc R U . . .
C7 C 0.8286(8) 0.9371(2) 1.0939(2) 0.0681(10) Uani 1 1 d . . . . .
C8 C 0.6138(6) 0.8695(2) 0.87062(16) 0.0630(9) Uani 1 1 d . . . . .
H8A H 0.5606 0.9235 0.8596 0.076 Uiso 1 1 calc R U . . .
H8B H 0.4771 0.8350 0.8727 0.076 Uiso 1 1 calc R U . . .
C9 C 0.7705(6) 0.8408(2) 0.81233(16) 0.0572(8) Uani 1 1 d . . . . .
C10 C 0.7510(7) 0.8750(2) 0.74691(19) 0.0735(10) Uani 1 1 d . . . . .
H10 H 0.6409 0.9153 0.7394 0.088 Uiso 1 1 calc R U . . .
C11 C 0.8917(9) 0.8506(3) 0.6923(2) 0.0906(13) Uani 1 1 d . . . . .
H11 H 0.8783 0.8747 0.6484 0.109 Uiso 1 1 calc R U . . .
C12 C 1.0483(10) 0.7918(3) 0.7029(2) 0.1017(16) Uani 1 1 d . . . . .
H12 H 1.1429 0.7753 0.6658 0.122 Uiso 1 1 calc R U . . .
C13 C 1.0718(10) 0.7554(3) 0.7675(2) 0.0937(14) Uani 1 1 d . . . . .
C14 C 0.9297(8) 0.7795(2) 0.82229(18) 0.0729(10) Uani 1 1 d . . . . .
H14 H 0.9414 0.7543 0.8658 0.087 Uiso 1 1 calc R U . . .
C15 C 0.9998(7) 1.0404(2) 0.83107(18) 0.0676(10) Uani 1 1 d . . . . .
C16 C 1.1559(10) 1.0449(3) 0.7682(2) 0.0987(15) Uani 1 1 d . . . . .
H16A H 1.0849 1.0786 0.7332 0.148 Uiso 1 1 calc R U . . .
H16B H 1.1788 0.9919 0.7495 0.148 Uiso 1 1 calc R U . . .
H16C H 1.3042 1.0672 0.7817 0.148 Uiso 1 1 calc R U . . .
C17 C 1.4255(7) 1.1405(2) 0.97464(19) 0.0626(8) Uani 1 1 d . . . . .
C18 C 1.4498(9) 1.2147(2) 0.9321(2) 0.0923(13) Uani 1 1 d . . . . .
H18A H 1.6122 1.2290 0.9287 0.138 Uiso 1 1 calc R U . . .
H18B H 1.3650 1.2577 0.9541 0.138 Uiso 1 1 calc R U . . .
H18C H 1.3881 1.2055 0.8859 0.138 Uiso 1 1 calc R U . . .
H3 H 1.085(6) 0.8672(19) 0.9486(16) 0.058(9) Uiso 1 1 d . . . . .
H4 H 0.846(5) 1.0218(16) 0.9502(14) 0.035(7) Uiso 1 1 d . . . . .
H5 H 1.330(6) 0.9979(18) 0.9986(16) 0.055(8) Uiso 1 1 d . . . . .
H2 H 0.964(6) 0.827(2) 1.0521(19) 0.075(11) Uiso 1 1 d . . . . .
H13 H 1.197(10) 0.709(3) 0.778(2) 0.126(17) Uiso 1 1 d . . . . .
H7A H 0.708(7) 0.982(2) 1.0796(19) 0.068(10) Uiso 1 1 d . . . . .
H7B H 0.795(7) 0.911(2) 1.135(2) 0.077(11) Uiso 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
O1 C1 1.216(4) . ?
O2 C6 1.418(4) . ?
O2 C7 1.428(5) . ?
O3 C15 1.347(4) . ?
O3 C4 1.454(4) . ?
O4 C15 1.193(5) . ?
O5 C17 1.339(4) . ?
O5 C5 1.446(4) . ?
O6 C17 1.201(4) . ?
N1 C1 1.344(4) . ?
N1 C8 1.451(4) . ?
N1 C3 1.468(4) . ?
C1 C2 1.521(5) . ?
C2 C7 1.508(5) . ?
C2 C3 1.555(4) . ?
C2 H2 0.96(4) . ?
C3 C4 1.506(4) . ?
C3 H3 1.00(4) . ?
C4 C5 1.521(5) . ?
C4 H4 1.01(3) . ?
C5 C6 1.528(5) . ?
C5 H5 1.04(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 1.06(4) . ?
C7 H7B 0.91(4) . ?
C8 C9 1.504(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.374(5) . ?
C9 C14 1.379(5) . ?
C10 C11 1.375(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.339(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(6) . ?
C13 H13 1.07(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.494(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.482(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C6 O2 C7 113.1(3) . . ?
C15 O3 C4 119.3(3) . . ?
C17 O5 C5 118.4(3) . . ?
C1 N1 C8 131.2(3) . . ?
C1 N1 C3 95.5(2) . . ?
C8 N1 C3 133.3(3) . . ?
O1 C1 N1 130.9(3) . . ?
O1 C1 C2 136.4(3) . . ?
N1 C1 C2 92.6(3) . . ?
C7 C2 C1 114.7(3) . . ?
C7 C2 C3 117.9(3) . . ?
C1 C2 C3 85.2(2) . . ?
C7 C2 H2 118(2) . . ?
C1 C2 H2 109(2) . . ?
C3 C2 H2 108(2) . . ?
N1 C3 C4 114.7(3) . . ?
N1 C3 C2 86.7(2) . . ?
C4 C3 C2 120.5(3) . . ?
N1 C3 H3 112.2(18) . . ?
C4 C3 H3 111.0(19) . . ?
C2 C3 H3 109.7(18) . . ?
O3 C4 C3 105.7(2) . . ?
O3 C4 C5 105.5(3) . . ?
C3 C4 C5 114.9(3) . . ?
O3 C4 H4 108.8(15) . . ?
C3 C4 H4 112.8(16) . . ?
C5 C4 H4 108.8(15) . . ?
O5 C5 C4 104.5(3) . . ?
O5 C5 C6 106.2(3) . . ?
C4 C5 C6 115.3(3) . . ?
O5 C5 H5 107.5(18) . . ?
C4 C5 H5 112.2(17) . . ?
C6 C5 H5 110.6(18) . . ?
O2 C6 C5 114.7(3) . . ?
O2 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
O2 C6 H6B 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
O2 C7 C2 111.4(3) . . ?
O2 C7 H7A 107.2(19) . . ?
C2 C7 H7A 115(2) . . ?
O2 C7 H7B 100(3) . . ?
C2 C7 H7B 107(2) . . ?
H7A C7 H7B 115(3) . . ?
N1 C8 C9 113.9(3) . . ?
N1 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C14 119.0(3) . . ?
C10 C9 C8 119.3(3) . . ?
C14 C9 C8 121.8(3) . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 119.5(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 121.3(4) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C14 119.4(4) . . ?
C12 C13 H13 123(3) . . ?
C14 C13 H13 117(3) . . ?
C9 C14 C13 119.9(4) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
O4 C15 O3 123.2(3) . . ?
O4 C15 C16 126.9(4) . . ?
O3 C15 C16 109.9(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 O5 122.8(3) . . ?
O6 C17 C18 125.6(4) . . ?
O5 C17 C18 111.6(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C8 N1 C1 O1 0.4(6) . . . . ?
C3 N1 C1 O1 179.4(4) . . . . ?
C8 N1 C1 C2 -177.6(3) . . . . ?
C3 N1 C1 C2 1.4(3) . . . . ?
O1 C1 C2 C7 -60.6(5) . . . . ?
N1 C1 C2 C7 117.2(3) . . . . ?
O1 C1 C2 C3 -179.1(4) . . . . ?
N1 C1 C2 C3 -1.3(2) . . . . ?
C1 N1 C3 C4 -123.5(3) . . . . ?
C8 N1 C3 C4 55.5(4) . . . . ?
C1 N1 C3 C2 -1.3(3) . . . . ?
C8 N1 C3 C2 177.6(3) . . . . ?
C7 C2 C3 N1 -114.2(3) . . . . ?
C1 C2 C3 N1 1.2(2) . . . . ?
C7 C2 C3 C4 2.6(5) . . . . ?
C1 C2 C3 C4 118.1(3) . . . . ?
C15 O3 C4 C3 127.5(3) . . . . ?
C15 O3 C4 C5 -110.4(3) . . . . ?
N1 C3 C4 O3 -86.3(3) . . . . ?
C2 C3 C4 O3 172.4(3) . . . . ?
N1 C3 C4 C5 157.9(3) . . . . ?
C2 C3 C4 C5 56.5(4) . . . . ?
C17 O5 C5 C4 -150.9(3) . . . . ?
C17 O5 C5 C6 86.8(4) . . . . ?
O3 C4 C5 O5 53.9(3) . . . . ?
C3 C4 C5 O5 169.9(3) . . . . ?
O3 C4 C5 C6 170.0(2) . . . . ?
C3 C4 C5 C6 -74.0(4) . . . . ?
C7 O2 C6 C5 -74.7(4) . . . . ?
O5 C5 C6 O2 -178.7(3) . . . . ?
C4 C5 C6 O2 66.1(4) . . . . ?
C6 O2 C7 C2 91.4(4) . . . . ?
C1 C2 C7 O2 -165.0(3) . . . . ?
C3 C2 C7 O2 -67.0(4) . . . . ?
C1 N1 C8 C9 -133.4(3) . . . . ?
C3 N1 C8 C9 48.0(5) . . . . ?
N1 C8 C9 C10 -144.4(3) . . . . ?
N1 C8 C9 C14 37.2(5) . . . . ?
C14 C9 C10 C11 -1.8(6) . . . . ?
C8 C9 C10 C11 179.7(4) . . . . ?
C9 C10 C11 C12 0.8(7) . . . . ?
C10 C11 C12 C13 -0.2(8) . . . . ?
C11 C12 C13 C14 0.6(8) . . . . ?
C10 C9 C14 C13 2.2(6) . . . . ?
C8 C9 C14 C13 -179.4(4) . . . . ?
C12 C13 C14 C9 -1.6(7) . . . . ?
C4 O3 C15 O4 -10.2(5) . . . . ?
C4 O3 C15 C16 169.8(3) . . . . ?
C5 O5 C17 O6 -6.0(5) . . . . ?
C5 O5 C17 C18 173.5(3) . . . . ?

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
C7 H7A O6 1.06(4) 2.63(4) 3.611(5) 155(3) 1_455
C4 H4 O6 1.01(3) 2.47(3) 3.383(4) 150(2) 1_455
C6 H6B O6 0.97 2.47 3.347(5) 150.7 1_455

_refine_diff_density_max         0.119
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.032

_shelxl_version_number           2014-3

