# 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. 
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#######################################################################

data_2ver0-21974_pps-192_auto
_database_code_depnum_ccdc_archive 'CCDC 2208381'
loop_
_audit_author_name
_audit_author_address
'Olga Bakulina'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2022-09-20 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_audit_creation_date             2022-09-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   13.2559(2)
_cell_length_b                   8.60080(10)
_cell_length_c                   14.9878(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.098(2)
_cell_angle_gamma                90
_cell_volume                     1657.31(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7128
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      69.0980
_cell_measurement_theta_min      3.9830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10828
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.199
_diffrn_reflns_theta_min         3.997
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2689
_reflns_number_total             3086
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3086
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.4920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.16793(7) 0.71185(10) 0.66021(6) 0.0218(2) Uani 1 1 d . . . . .
O2 O 0.39685(7) 0.81126(10) 0.63092(6) 0.0198(2) Uani 1 1 d . . . . .
O3 O 0.39109(8) 0.68911(11) 0.49701(6) 0.0280(2) Uani 1 1 d . . . . .
O4 O 0.47917(7) 0.67130(11) 0.88114(6) 0.0259(2) Uani 1 1 d . . . . .
N1 N 0.30578(8) 0.56767(12) 0.74865(7) 0.0181(2) Uani 1 1 d . . . . .
C1 C 0.24633(9) 0.63289(14) 0.67296(8) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.31432(9) 0.56721(14) 0.61061(8) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.38151(9) 0.49424(14) 0.70460(8) 0.0168(3) Uani 1 1 d . . . . .
H3 H 0.374390 0.378483 0.704321 0.020 Uiso 1 1 calc R U . . .
C4 C 0.49425(9) 0.54180(14) 0.73847(8) 0.0175(3) Uani 1 1 d . . . . .
C5 C 0.53551(10) 0.62564(15) 0.81931(9) 0.0207(3) Uani 1 1 d . . . . .
C6 C 0.41071(10) 0.55668(16) 0.90342(8) 0.0230(3) Uani 1 1 d . . . . .
H6A H 0.409848 0.566609 0.969041 0.028 Uiso 1 1 calc R U . . .
H6B H 0.436638 0.451521 0.893942 0.028 Uiso 1 1 calc R U . . .
C7 C 0.30210(10) 0.57609(15) 0.84446(8) 0.0206(3) Uani 1 1 d . . . . .
H7A H 0.256553 0.492997 0.858367 0.025 Uiso 1 1 calc R U . . .
H7B H 0.273481 0.677748 0.857183 0.025 Uiso 1 1 calc R U . . .
C8 C 0.63967(10) 0.67018(16) 0.84166(10) 0.0259(3) Uani 1 1 d . . . . .
H8 H 0.666293 0.729771 0.895629 0.031 Uiso 1 1 calc R U . . .
C9 C 0.70488(10) 0.62863(16) 0.78615(10) 0.0275(3) Uani 1 1 d . . . . .
H9 H 0.775452 0.661348 0.801351 0.033 Uiso 1 1 calc R U . . .
C10 C 0.66664(10) 0.53882(16) 0.70806(9) 0.0248(3) Uani 1 1 d . . . . .
H10 H 0.711519 0.505962 0.671039 0.030 Uiso 1 1 calc R U . . .
C11 C 0.56239(10) 0.49775(15) 0.68481(8) 0.0199(3) Uani 1 1 d . . . . .
H11 H 0.536395 0.437905 0.630822 0.024 Uiso 1 1 calc R U . . .
C12 C 0.25967(10) 0.45318(14) 0.53791(8) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.31299(10) 0.32876(15) 0.51117(8) 0.0211(3) Uani 1 1 d . . . . .
H13 H 0.384603 0.313653 0.539582 0.025 Uiso 1 1 calc R U . . .
C14 C 0.26195(11) 0.22679(15) 0.44323(9) 0.0236(3) Uani 1 1 d . . . . .
H14 H 0.298694 0.141950 0.425572 0.028 Uiso 1 1 calc R U . . .
C15 C 0.15738(11) 0.24840(15) 0.40098(9) 0.0241(3) Uani 1 1 d . . . . .
H15 H 0.122757 0.179035 0.354142 0.029 Uiso 1 1 calc R U . . .
C16 C 0.10384(11) 0.37122(17) 0.42734(9) 0.0253(3) Uani 1 1 d . . . . .
H16 H 0.032167 0.385652 0.398890 0.030 Uiso 1 1 calc R U . . .
C17 C 0.15466(10) 0.47387(16) 0.49547(8) 0.0226(3) Uani 1 1 d . . . . .
H17 H 0.117580 0.558356 0.513076 0.027 Uiso 1 1 calc R U . . .
C18 C 0.37125(9) 0.69345(14) 0.57120(8) 0.0183(3) Uani 1 1 d . . . . .
C19 C 0.45979(11) 0.93353(16) 0.60529(10) 0.0258(3) Uani 1 1 d . . . . .
H19A H 0.417852 0.995168 0.553620 0.031 Uiso 1 1 calc R U . . .
H19B H 0.519574 0.888066 0.585718 0.031 Uiso 1 1 calc R U . . .
C20 C 0.49761(11) 1.03540(17) 0.68832(11) 0.0312(3) Uani 1 1 d . . . . .
H20A H 0.536179 1.123759 0.671933 0.047 Uiso 1 1 calc R U . . .
H20B H 0.543343 0.975114 0.737407 0.047 Uiso 1 1 calc R U . . .
H20C H 0.437934 1.073693 0.709702 0.047 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 1.2171(15) . ?
O2 C18 1.3398(15) . ?
O2 C19 1.4511(15) . ?
O3 C18 1.2040(16) . ?
O4 C5 1.3813(15) . ?
O4 C6 1.4335(16) . ?
N1 C1 1.3368(16) . ?
N1 C3 1.4715(15) . ?
N1 C7 1.4504(15) . ?
C1 C2 1.5540(16) . ?
C2 C3 1.6001(16) . ?
C2 C12 1.5131(17) . ?
C2 C18 1.5212(17) . ?
C3 H3 1.0000 . ?
C3 C4 1.5129(17) . ?
C4 C5 1.4015(18) . ?
C4 C11 1.4002(17) . ?
C5 C8 1.3929(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5039(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 0.9500 . ?
C8 C9 1.385(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3861(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3939(18) . ?
C12 C17 1.3937(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3886(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3932(19) . ?
C17 H17 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.505(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C18 O2 C19 116.08(10) . . ?
C5 O4 C6 115.92(10) . . ?
C1 N1 C3 97.17(9) . . ?
C1 N1 C7 131.62(11) . . ?
C7 N1 C3 131.05(10) . . ?
O1 C1 N1 132.20(11) . . ?
O1 C1 C2 134.96(11) . . ?
N1 C1 C2 92.84(9) . . ?
C1 C2 C3 83.87(8) . . ?
C12 C2 C1 115.00(10) . . ?
C12 C2 C3 116.48(10) . . ?
C12 C2 C18 112.26(10) . . ?
C18 C2 C1 112.91(10) . . ?
C18 C2 C3 113.53(10) . . ?
N1 C3 C2 86.12(8) . . ?
N1 C3 H3 110.8 . . ?
N1 C3 C4 117.35(10) . . ?
C2 C3 H3 110.8 . . ?
C4 C3 C2 118.81(10) . . ?
C4 C3 H3 110.8 . . ?
C5 C4 C3 125.09(11) . . ?
C11 C4 C3 117.18(11) . . ?
C11 C4 C5 117.73(12) . . ?
O4 C5 C4 124.43(11) . . ?
O4 C5 C8 115.26(11) . . ?
C8 C5 C4 120.31(12) . . ?
O4 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
O4 C6 C7 110.89(11) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
N1 C7 C6 108.55(10) . . ?
N1 C7 H7A 110.0 . . ?
N1 C7 H7B 110.0 . . ?
C6 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C5 C8 H8 119.6 . . ?
C9 C8 C5 120.79(13) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.74(13) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.33(12) . . ?
C11 C10 H10 120.3 . . ?
C4 C11 H11 119.0 . . ?
C10 C11 C4 121.99(12) . . ?
C10 C11 H11 119.0 . . ?
C13 C12 C2 121.15(11) . . ?
C17 C12 C2 119.71(11) . . ?
C17 C12 C13 119.13(11) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.34(12) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.24(12) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.78(12) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.22(12) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.30(12) . . ?
C16 C17 H17 119.9 . . ?
O2 C18 C2 110.45(10) . . ?
O3 C18 O2 124.31(12) . . ?
O3 C18 C2 125.25(11) . . ?
O2 C19 H19A 110.2 . . ?
O2 C19 H19B 110.2 . . ?
O2 C19 C20 107.47(11) . . ?
H19A C19 H19B 108.5 . . ?
C20 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 C1 C2 C3 -179.45(15) . . . . ?
O1 C1 C2 C12 -63.04(19) . . . . ?
O1 C1 C2 C18 67.56(18) . . . . ?
O4 C5 C8 C9 178.64(12) . . . . ?
O4 C6 C7 N1 56.76(13) . . . . ?
N1 C1 C2 C3 -0.32(9) . . . . ?
N1 C1 C2 C12 116.08(11) . . . . ?
N1 C1 C2 C18 -113.31(10) . . . . ?
N1 C3 C4 C5 13.21(17) . . . . ?
N1 C3 C4 C11 -167.07(11) . . . . ?
C1 N1 C3 C2 -0.34(9) . . . . ?
C1 N1 C3 C4 120.24(11) . . . . ?
C1 N1 C7 C6 -150.37(13) . . . . ?
C1 C2 C3 N1 0.29(8) . . . . ?
C1 C2 C3 C4 -118.94(11) . . . . ?
C1 C2 C12 C13 -145.89(11) . . . . ?
C1 C2 C12 C17 35.30(16) . . . . ?
C1 C2 C18 O2 33.11(13) . . . . ?
C1 C2 C18 O3 -147.04(12) . . . . ?
C2 C3 C4 C5 114.61(13) . . . . ?
C2 C3 C4 C11 -65.67(14) . . . . ?
C2 C12 C13 C14 -178.91(11) . . . . ?
C2 C12 C17 C16 178.93(11) . . . . ?
C3 N1 C1 O1 179.51(14) . . . . ?
C3 N1 C1 C2 0.35(10) . . . . ?
C3 N1 C7 C6 24.05(18) . . . . ?
C3 C2 C12 C13 -50.12(15) . . . . ?
C3 C2 C12 C17 131.07(12) . . . . ?
C3 C2 C18 O2 -60.19(13) . . . . ?
C3 C2 C18 O3 119.66(13) . . . . ?
C3 C4 C5 O4 2.6(2) . . . . ?
C3 C4 C5 C8 -176.74(12) . . . . ?
C3 C4 C11 C10 178.20(11) . . . . ?
C4 C5 C8 C9 -2.0(2) . . . . ?
C5 O4 C6 C7 -95.32(13) . . . . ?
C5 C4 C11 C10 -2.06(18) . . . . ?
C5 C8 C9 C10 -1.3(2) . . . . ?
C6 O4 C5 C4 43.78(17) . . . . ?
C6 O4 C5 C8 -136.85(12) . . . . ?
C7 N1 C1 O1 -4.7(2) . . . . ?
C7 N1 C1 C2 176.11(13) . . . . ?
C7 N1 C3 C2 -176.14(13) . . . . ?
C7 N1 C3 C4 -55.55(17) . . . . ?
C8 C9 C10 C11 2.7(2) . . . . ?
C9 C10 C11 C4 -1.07(19) . . . . ?
C11 C4 C5 O4 -177.11(11) . . . . ?
C11 C4 C5 C8 3.54(18) . . . . ?
C12 C2 C3 N1 -114.63(11) . . . . ?
C12 C2 C3 C4 126.14(12) . . . . ?
C12 C2 C18 O2 165.08(10) . . . . ?
C12 C2 C18 O3 -15.07(17) . . . . ?
C12 C13 C14 C15 0.32(19) . . . . ?
C13 C12 C17 C16 0.09(18) . . . . ?
C13 C14 C15 C16 -0.54(19) . . . . ?
C14 C15 C16 C17 0.54(19) . . . . ?
C15 C16 C17 C12 -0.3(2) . . . . ?
C17 C12 C13 C14 -0.09(18) . . . . ?
C18 O2 C19 C20 -168.70(11) . . . . ?
C18 C2 C3 N1 112.64(10) . . . . ?
C18 C2 C3 C4 -6.59(15) . . . . ?
C18 C2 C12 C13 83.19(14) . . . . ?
C18 C2 C12 C17 -95.62(13) . . . . ?
C19 O2 C18 O3 -5.15(18) . . . . ?
C19 O2 C18 C2 174.70(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
