# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_depaolis1_a
_database_code_depnum_ccdc_archive 'CCDC 2162117'
loop_
_audit_author_name
_audit_author_address
'Jean-Francois Lohier'
;ENSICAEN
France
;
_audit_update_record             
;
2022-03-25 deposited with the CCDC.	2023-01-27 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         'C20 H19 N O5'
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   14.8529(12)
_cell_length_b                   20.5937(18)
_cell_length_c                   5.5853(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1708.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      39.44

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   0.6432
_exptl_transmission_factor_max   0.7477
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    0.099
_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   'Sadabs 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19211
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.916
_diffrn_reflns_theta_max         29.572
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4754
_reflns_number_gt                4581
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.991

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0515P)²+0.2190P] 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_abs_structure_details 
;
 Flack x determined using 1845 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4754
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
O3 O 0.47855(7) 0.48439(5) 0.7350(2) 0.0205(2) Uani 1 1 d . . . . .
O4 O 0.64787(8) 0.44400(5) 0.0768(3) 0.0258(3) Uani 1 1 d . . . . .
O1 O 0.36830(7) 0.39953(5) 0.3312(2) 0.0213(2) Uani 1 1 d . . . . .
O2 O 0.28701(8) 0.40611(7) 0.6714(2) 0.0278(3) Uani 1 1 d . . . . .
O5 O 0.68193(8) 0.50780(7) -0.2182(3) 0.0324(3) Uani 1 1 d . . . . .
N1 N 0.65372(8) 0.49795(7) -0.0151(3) 0.0211(3) Uani 1 1 d . . . . .
C5 C 0.50412(9) 0.45968(7) 0.5502(3) 0.0149(3) Uani 1 1 d . . . . .
C4 C 0.54607(10) 0.39242(7) 0.5518(3) 0.0179(3) Uani 1 1 d . . . . .
H4A H 0.609879 0.395980 0.601365 0.021 Uiso 1 1 calc R U . . .
H4B H 0.544712 0.374454 0.387482 0.021 Uiso 1 1 calc R U . . .
C15 C 0.55613(10) 0.55212(7) 0.2897(3) 0.0178(3) Uani 1 1 d . . . . .
C16 C 0.62770(10) 0.55476(7) 0.1282(3) 0.0196(3) Uani 1 1 d . . . . .
C6 C 0.49166(9) 0.49513(7) 0.3105(3) 0.0155(3) Uani 1 1 d . . . . .
H6 H 0.503914 0.464014 0.176992 0.019 Uiso 1 1 calc R U . . .
C7 C 0.39222(10) 0.51698(7) 0.2968(3) 0.0207(3) Uani 1 1 d . . . . .
H7A H 0.373827 0.535778 0.452443 0.025 Uiso 1 1 calc R U . . .
H7B H 0.385707 0.551009 0.172831 0.025 Uiso 1 1 calc R U . . .
C9 C 0.55682(11) 0.28641(7) 0.7684(3) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.34524(10) 0.38080(8) 0.5543(3) 0.0224(3) Uani 1 1 d . . . . .
C3 C 0.49692(10) 0.34523(7) 0.7223(3) 0.0200(3) Uani 1 1 d . . . . .
H3 H 0.488070 0.368094 0.878492 0.024 Uiso 1 1 calc R U . . .
C17 C 0.68042(11) 0.60958(8) 0.0938(4) 0.0285(4) Uani 1 1 d . . . . .
H17 H 0.726557 0.609858 -0.023982 0.034 Uiso 1 1 calc R U . . .
C8 C 0.33120(10) 0.45961(8) 0.2360(3) 0.0220(3) Uani 1 1 d . . . . .
H8A H 0.270594 0.467031 0.304511 0.026 Uiso 1 1 calc R U . . .
H8B H 0.324981 0.456003 0.060025 0.026 Uiso 1 1 calc R U . . .
C10 C 0.60820(12) 0.28452(9) 0.9752(3) 0.0270(4) Uani 1 1 d . . . . .
H10 H 0.604178 0.319277 1.086529 0.032 Uiso 1 1 calc R U . . .
C11 C 0.66556(13) 0.23277(10) 1.0231(4) 0.0318(4) Uani 1 1 d . . . . .
H11 H 0.699250 0.232080 1.167629 0.038 Uiso 1 1 calc R U . . .
C14 C 0.56585(13) 0.23555(9) 0.6068(4) 0.0310(4) Uani 1 1 d . . . . .
H14 H 0.531684 0.235783 0.463029 0.037 Uiso 1 1 calc R U . . .
C20 C 0.54191(12) 0.60798(8) 0.4268(3) 0.0283(4) Uani 1 1 d . . . . .
H20 H 0.494136 0.608736 0.539858 0.034 Uiso 1 1 calc R U . . .
C2 C 0.40330(12) 0.32447(9) 0.6299(4) 0.0314(4) Uani 1 1 d . . . . .
H2A H 0.411221 0.294874 0.491825 0.038 Uiso 1 1 calc R U . . .
H2B H 0.371913 0.300032 0.757691 0.038 Uiso 1 1 calc R U . . .
C19 C 0.59622(14) 0.66236(9) 0.4009(4) 0.0359(4) Uani 1 1 d . . . . .
H19 H 0.586151 0.699208 0.499660 0.043 Uiso 1 1 calc R U . . .
C13 C 0.62435(14) 0.18424(9) 0.6530(4) 0.0367(4) Uani 1 1 d . . . . .
H13 H 0.630318 0.150096 0.539761 0.044 Uiso 1 1 calc R U . . .
C12 C 0.67376(12) 0.18262(8) 0.8623(4) 0.0316(4) Uani 1 1 d . . . . .
H12 H 0.712957 0.147253 0.894818 0.038 Uiso 1 1 calc R U . . .
C18 C 0.66476(13) 0.66373(8) 0.2335(4) 0.0356(4) Uani 1 1 d . . . . .
H18 H 0.700727 0.701539 0.214802 0.043 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
O3 C5 1.2119(17) . ?
O4 N1 1.2270(18) . ?
O1 C1 1.349(2) . ?
O1 C8 1.4551(19) . ?
O2 C1 1.203(2) . ?
O5 N1 1.226(2) . ?
N1 C16 1.469(2) . ?
C5 C4 1.519(2) . ?
C5 C6 1.536(2) . ?
C4 C3 1.544(2) . ?
C15 C16 1.396(2) . ?
C15 C20 1.398(2) . ?
C15 C6 1.5190(19) . ?
C16 C17 1.387(2) . ?
C6 C7 1.546(2) . ?
C7 C8 1.527(2) . ?
C9 C10 1.385(2) . ?
C9 C14 1.389(2) . ?
C9 C3 1.525(2) . ?
C1 C2 1.506(2) . ?
C3 C2 1.544(2) . ?
C17 C18 1.381(3) . ?
C10 C11 1.390(2) . ?
C11 C12 1.374(3) . ?
C14 C13 1.392(3) . ?
C20 C19 1.388(3) . ?
C19 C18 1.382(3) . ?
C13 C12 1.381(3) . ?

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 C8 118.99(13) . . ?
O5 N1 O4 124.14(15) . . ?
O5 N1 C16 117.51(14) . . ?
O4 N1 C16 118.33(14) . . ?
O3 C5 C4 120.43(13) . . ?
O3 C5 C6 120.32(13) . . ?
C4 C5 C6 119.22(12) . . ?
C5 C4 C3 112.57(12) . . ?
C16 C15 C20 115.92(14) . . ?
C16 C15 C6 124.04(13) . . ?
C20 C15 C6 119.92(14) . . ?
C17 C16 C15 123.45(15) . . ?
C17 C16 N1 115.11(15) . . ?
C15 C16 N1 121.43(13) . . ?
C15 C6 C5 110.97(12) . . ?
C15 C6 C7 111.94(12) . . ?
C5 C6 C7 107.25(12) . . ?
C8 C7 C6 110.67(12) . . ?
C10 C9 C14 117.87(15) . . ?
C10 C9 C3 118.99(14) . . ?
C14 C9 C3 123.07(15) . . ?
O2 C1 O1 124.11(16) . . ?
O2 C1 C2 126.38(17) . . ?
O1 C1 C2 109.50(15) . . ?
C9 C3 C2 111.23(13) . . ?
C9 C3 C4 109.17(12) . . ?
C2 C3 C4 113.20(14) . . ?
C18 C17 C16 118.95(18) . . ?
O1 C8 C7 110.59(11) . . ?
C9 C10 C11 121.30(16) . . ?
C12 C11 C10 120.32(18) . . ?
C9 C14 C13 120.81(18) . . ?
C19 C20 C15 121.28(17) . . ?
C1 C2 C3 113.35(14) . . ?
C18 C19 C20 121.00(17) . . ?
C12 C13 C14 120.46(17) . . ?
C11 C12 C13 119.22(16) . . ?
C17 C18 C19 119.32(16) . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.039



