# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc2dr32c
_database_code_depnum_ccdc_archive 'CCDC 2226732'
loop_
_audit_author_name
_audit_author_address
'clement denhez'
;Universite de Reims Champagne Ardenne, Institut de Chimie Moleculaire de Reims
France
;
_audit_update_record             
;
2022-12-15 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H28 N2 O6'
_chemical_formula_weight         476.51

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   11.6688(4)
_cell_length_b                   7.6572(2)
_cell_length_c                   13.4891(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.345(2)
_cell_angle_gamma                90
_cell_volume                     1181.71(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      72.11

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.144
_exptl_absorpt_coefficient_mu    0.781
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6326
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38819
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.342
_diffrn_reflns_theta_max         72.198
_diffrn_reflns_theta_full        67.679
_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 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4648
_reflns_number_gt                4265
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.998

_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0367P)²+0.4035P] 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 1809 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4648
_refine_ls_number_parameters     316
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.61576(13) 0.3394(2) 0.61269(11) 0.0169(3) Uani 1 1 d . . . . .
O2 O 0.51876(14) 0.4965(2) 0.48068(13) 0.0232(4) Uani 1 1 d . . . . .
O6 O 0.83808(18) 0.3569(3) 0.16377(15) 0.0427(5) Uani 1 1 d . . . . .
O3 O 1.00503(18) 0.1414(3) 0.60891(18) 0.0466(6) Uani 1 1 d . . . . .
N2 N 0.7539(2) 0.3831(3) 0.20327(17) 0.0315(5) Uani 1 1 d . . . . .
O5 O 0.66102(19) 0.4447(4) 0.16100(14) 0.0479(6) Uani 1 1 d . . . . .
N1 N 0.9908(2) 0.1528(3) 0.5171(2) 0.0357(6) Uani 1 1 d . . . . .
O4 O 1.0638(2) 0.1084(3) 0.4680(2) 0.0561(7) Uani 1 1 d . . . . .
C21 C 0.59794(19) 0.4024(3) 0.51774(17) 0.0176(5) Uani 1 1 d . . . . .
C10 C 0.56831(18) 0.4453(3) 0.76628(16) 0.0146(4) Uani 1 1 d . . . . .
C9 C 0.53052(19) 0.3762(3) 0.67169(17) 0.0162(5) Uani 1 1 d . . . . .
C26 C 0.7940(2) 0.2676(3) 0.51531(19) 0.0205(5) Uani 1 1 d . . . . .
H26 H 0.804659 0.243294 0.585585 0.025 Uiso 1 1 calc R U . . .
C17 C 0.75468(19) 0.6150(3) 0.74063(17) 0.0155(5) Uani 1 1 d . . . . .
H17 H 0.767928 0.545096 0.681261 0.019 Uiso 1 1 calc R U . . .
C11 C 0.69557(19) 0.4924(3) 0.80705(16) 0.0153(4) Uani 1 1 d . . . . .
H11 H 0.697279 0.555524 0.872228 0.018 Uiso 1 1 calc R U . . .
C8 C 0.4146(2) 0.3271(3) 0.63175(17) 0.0189(5) Uani 1 1 d . . . . .
H8 H 0.393858 0.281254 0.565188 0.023 Uiso 1 1 calc R U . . .
C7 C 0.33221(19) 0.3464(3) 0.69001(18) 0.0212(5) Uani 1 1 d . . . . .
H7 H 0.253416 0.314589 0.663668 0.025 Uiso 1 1 calc R U . . .
C22 C 0.69230(19) 0.3453(3) 0.46407(18) 0.0177(5) Uani 1 1 d . . . . .
C18 C 0.6802(2) 0.7740(3) 0.69886(18) 0.0187(5) Uani 1 1 d . . . . .
H18 H 0.607949 0.728626 0.653803 0.022 Uiso 1 1 calc R U . . .
C13 C 0.8952(2) 0.3655(3) 0.88736(18) 0.0208(5) Uani 1 1 d . . . . .
H13 H 0.892621 0.415612 0.955332 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3632(2) 0.4133(3) 0.78907(18) 0.0191(5) Uani 1 1 d . . . . .
C23 C 0.6773(2) 0.3812(3) 0.36122(18) 0.0215(5) Uani 1 1 d . . . . .
H23 H 0.607706 0.434798 0.325944 0.026 Uiso 1 1 calc R U . . .
C15 C 0.9513(2) 0.5002(3) 0.82846(18) 0.0213(5) Uani 1 1 d . . . . .
H15A H 0.964819 0.446485 0.765003 0.026 Uiso 1 1 calc R U . . .
H15B H 1.028165 0.534554 0.868980 0.026 Uiso 1 1 calc R U . . .
C12 C 0.7697(2) 0.3259(3) 0.83364(17) 0.0181(5) Uani 1 1 d . . . . .
H12A H 0.732107 0.250723 0.877726 0.022 Uiso 1 1 calc R U . . .
H12B H 0.771495 0.260242 0.770754 0.022 Uiso 1 1 calc R U . . .
C1 C 0.5068(2) 0.5292(3) 0.92906(17) 0.0209(5) Uani 1 1 d . . . . .
H1 H 0.584686 0.562545 0.957874 0.025 Uiso 1 1 calc R U . . .
C6 C 0.48153(19) 0.4644(3) 0.82851(17) 0.0165(5) Uani 1 1 d . . . . .
C25 C 0.8687(2) 0.2587(3) 0.3593(2) 0.0262(6) Uani 1 1 d . . . . .
H25 H 0.928601 0.228573 0.323821 0.031 Uiso 1 1 calc R U . . .
C16 C 0.8758(2) 0.6636(3) 0.80278(18) 0.0195(5) Uani 1 1 d . . . . .
H16A H 0.914999 0.745791 0.763629 0.023 Uiso 1 1 calc R U . . .
H16B H 0.866381 0.722574 0.866009 0.023 Uiso 1 1 calc R U . . .
C2 C 0.4220(2) 0.5449(4) 0.98546(19) 0.0266(6) Uani 1 1 d . . . . .
H2 H 0.441584 0.590476 1.052168 0.032 Uiso 1 1 calc R U . . .
C27 C 0.8799(2) 0.2264(3) 0.4613(2) 0.0238(5) Uani 1 1 d . . . . .
C24 C 0.7663(2) 0.3368(4) 0.31150(19) 0.0248(5) Uani 1 1 d . . . . .
C19 C 0.6413(2) 0.8843(3) 0.7805(2) 0.0249(5) Uani 1 1 d . . . . .
H19A H 0.600830 0.809953 0.821768 0.037 Uiso 1 1 calc R U . . .
H19B H 0.709886 0.937464 0.823582 0.037 Uiso 1 1 calc R U . . .
H19C H 0.588234 0.976352 0.748640 0.037 Uiso 1 1 calc R U . . .
C4 C 0.2778(2) 0.4300(4) 0.8504(2) 0.0266(6) Uani 1 1 d . . . . .
H4 H 0.199528 0.395424 0.824269 0.032 Uiso 1 1 calc R U . . .
C20 C 0.7437(2) 0.8885(3) 0.63374(19) 0.0247(5) Uani 1 1 d . . . . .
H20A H 0.768319 0.816620 0.581578 0.037 Uiso 1 1 calc R U . . .
H20B H 0.690852 0.980570 0.601510 0.037 Uiso 1 1 calc R U . . .
H20C H 0.812504 0.941682 0.676452 0.037 Uiso 1 1 calc R U . . .
C3 C 0.3064(2) 0.4945(4) 0.94593(19) 0.0300(6) Uani 1 1 d . . . . .
H3 H 0.248223 0.505539 0.985889 0.036 Uiso 1 1 calc R U . . .
C14 C 0.9680(2) 0.1979(4) 0.9031(2) 0.0299(6) Uani 1 1 d . . . . .
H14A H 0.930508 0.113353 0.940971 0.045 Uiso 1 1 calc R U . . .
H14B H 0.973612 0.148347 0.837202 0.045 Uiso 1 1 calc R U . . .
H14C H 1.046575 0.224747 0.941078 0.045 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 C21 1.346(3) . ?
O1 C9 1.419(3) . ?
O2 C21 1.201(3) . ?
O6 N2 1.223(3) . ?
O3 N1 1.220(3) . ?
N2 O5 1.216(3) . ?
N2 C24 1.481(3) . ?
N1 O4 1.225(3) . ?
N1 C27 1.475(3) . ?
C21 C22 1.497(3) . ?
C10 C9 1.372(3) . ?
C10 C6 1.444(3) . ?
C10 C11 1.522(3) . ?
C9 C8 1.406(3) . ?
C26 C27 1.386(3) . ?
C26 C22 1.385(3) . ?
C26 H26 0.9500 . ?
C17 C18 1.537(3) . ?
C17 C16 1.540(3) . ?
C17 C11 1.550(3) . ?
C17 H17 1.0000 . ?
C11 C12 1.543(3) . ?
C11 H11 1.0000 . ?
C8 C7 1.364(3) . ?
C8 H8 0.9500 . ?
C7 C5 1.410(3) . ?
C7 H7 0.9500 . ?
C22 C23 1.391(3) . ?
C18 C19 1.526(3) . ?
C18 C20 1.531(3) . ?
C18 H18 1.0000 . ?
C13 C15 1.526(3) . ?
C13 C14 1.530(3) . ?
C13 C12 1.531(3) . ?
C13 H13 1.0000 . ?
C5 C4 1.421(3) . ?
C5 C6 1.433(3) . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C15 C16 1.530(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C1 C2 1.367(3) . ?
C1 C6 1.420(3) . ?
C1 H1 0.9500 . ?
C25 C24 1.378(4) . ?
C25 C27 1.378(4) . ?
C25 H25 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C2 C3 1.404(4) . ?
C2 H2 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C4 C3 1.359(4) . ?
C4 H4 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C3 H3 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C21 O1 C9 117.93(17) . . ?
O5 N2 O6 125.3(2) . . ?
O5 N2 C24 117.4(2) . . ?
O6 N2 C24 117.3(2) . . ?
O3 N1 O4 124.0(3) . . ?
O3 N1 C27 118.4(2) . . ?
O4 N1 C27 117.6(2) . . ?
O2 C21 O1 125.0(2) . . ?
O2 C21 C22 123.6(2) . . ?
O1 C21 C22 111.40(19) . . ?
C9 C10 C6 116.48(19) . . ?
C9 C10 C11 122.68(19) . . ?
C6 C10 C11 120.78(19) . . ?
C10 C9 C8 124.7(2) . . ?
C10 C9 O1 117.76(19) . . ?
C8 C9 O1 117.39(19) . . ?
C27 C26 C22 118.2(2) . . ?
C27 C26 H26 120.9 . . ?
C22 C26 H26 120.9 . . ?
C18 C17 C16 113.56(18) . . ?
C18 C17 C11 114.07(18) . . ?
C16 C17 C11 107.25(17) . . ?
C18 C17 H17 107.2 . . ?
C16 C17 H17 107.2 . . ?
C11 C17 H17 107.2 . . ?
C10 C11 C12 110.53(18) . . ?
C10 C11 C17 116.62(18) . . ?
C12 C11 C17 109.99(17) . . ?
C10 C11 H11 106.4 . . ?
C12 C11 H11 106.4 . . ?
C17 C11 H11 106.4 . . ?
C7 C8 C9 119.0(2) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C8 C7 C5 120.5(2) . . ?
C8 C7 H7 119.8 . . ?
C5 C7 H7 119.8 . . ?
C26 C22 C23 120.7(2) . . ?
C26 C22 C21 121.6(2) . . ?
C23 C22 C21 117.7(2) . . ?
C19 C18 C20 110.1(2) . . ?
C19 C18 C17 113.63(19) . . ?
C20 C18 C17 111.22(19) . . ?
C19 C18 H18 107.2 . . ?
C20 C18 H18 107.2 . . ?
C17 C18 H18 107.2 . . ?
C15 C13 C14 110.84(19) . . ?
C15 C13 C12 110.82(18) . . ?
C14 C13 C12 110.7(2) . . ?
C15 C13 H13 108.1 . . ?
C14 C13 H13 108.1 . . ?
C12 C13 H13 108.1 . . ?
C7 C5 C4 120.4(2) . . ?
C7 C5 C6 120.0(2) . . ?
C4 C5 C6 119.6(2) . . ?
C24 C23 C22 118.4(2) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C13 C15 C16 112.58(18) . . ?
C13 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C13 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C13 C12 C11 112.77(19) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C2 C1 C6 121.7(2) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C1 C6 C5 117.0(2) . . ?
C1 C6 C10 123.6(2) . . ?
C5 C6 C10 119.4(2) . . ?
C24 C25 C27 116.6(2) . . ?
C24 C25 H25 121.7 . . ?
C27 C25 H25 121.7 . . ?
C15 C16 C17 110.57(19) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C1 C2 C3 120.7(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C25 C27 C26 123.2(2) . . ?
C25 C27 N1 118.6(2) . . ?
C26 C27 N1 118.1(2) . . ?
C25 C24 C23 122.9(2) . . ?
C25 C24 N2 118.2(2) . . ?
C23 C24 N2 118.8(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
