# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_JH-iso_a
_audit_block_doi                 10.5517/ccdc.csd.cc2md2sx
_database_code_depnum_ccdc_archive 'CCDC 2424689'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/d1qo01780b 2022
loop_
_audit_author_name
_audit_author_address
'Deborah de Alencar Simoni'
;State University of Campinas
Brazil
;
#Added by publCIF



_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-02-27 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 N O5'
_chemical_formula_sum            'C22 H23 N O5'
_chemical_formula_weight         381.41

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.6317(8)
_cell_length_b                   8.1349(12)
_cell_length_c                   22.621(3)
_cell_angle_alpha                97.902(4)
_cell_angle_beta                 90.095(5)
_cell_angle_gamma                106.354(5)
_cell_volume                     984.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    61
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      21.65

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7039
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            21963
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.819
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4336
_reflns_number_gt                3418
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0484P)²+0.5141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         4336
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 1.11346(19) 0.63609(15) 0.45404(5) 0.0251(3) Uani 1 1 d . . . . .
O2 O 0.7880(2) 0.52740(14) 0.39067(5) 0.0248(3) Uani 1 1 d . . . . .
O3 O 0.3448(2) 0.34230(14) 0.18597(5) 0.0253(3) Uani 1 1 d . . . . .
O4 O 0.7093(2) 0.32605(18) 0.10783(6) 0.0410(3) Uani 1 1 d . . . . .
O5 O 0.4190(3) 0.2446(2) 0.03430(6) 0.0509(4) Uani 1 1 d . . . . .
N1 N 1.1864(2) 0.74097(17) 0.51025(6) 0.0246(3) Uani 1 1 d . . . . .
C1 C 0.8318(3) 0.9896(2) 0.59884(7) 0.0248(3) Uani 1 1 d . . . . .
H1 H 0.7078 0.9827 0.5706 0.030 Uiso 1 1 calc R U . . .
C2 C 0.8504(3) 1.0964(2) 0.65289(8) 0.0295(4) Uani 1 1 d . . . . .
H2 H 0.7394 1.1616 0.6607 0.035 Uiso 1 1 calc R U . . .
C3 C 1.0333(3) 1.1068(2) 0.69551(7) 0.0301(4) Uani 1 1 d . . . . .
H3 H 1.0457 1.1792 0.7317 0.036 Uiso 1 1 calc R U . . .
C4 C 1.1980(3) 1.0086(2) 0.68385(8) 0.0304(4) Uani 1 1 d . . . . .
H4 H 1.3202 1.0145 0.7124 0.036 Uiso 1 1 calc R U . . .
C5 C 1.1809(3) 0.9019(2) 0.62981(7) 0.0255(3) Uani 1 1 d . . . . .
H5 H 1.2915 0.8362 0.6223 0.031 Uiso 1 1 calc R U . . .
C6 C 0.9986(3) 0.89231(19) 0.58664(7) 0.0203(3) Uani 1 1 d . . . . .
C7 C 0.9865(3) 0.78349(19) 0.52841(7) 0.0199(3) Uani 1 1 d . . . . .
C8 C 0.7815(3) 0.71336(19) 0.48706(6) 0.0201(3) Uani 1 1 d . . . . .
H8 H 0.6227 0.7261 0.4898 0.024 Uiso 1 1 calc R U . . .
C9 C 0.8739(3) 0.6233(2) 0.44264(7) 0.0211(3) Uani 1 1 d . . . . .
C10 C 0.5427(3) 0.5302(2) 0.37243(7) 0.0234(3) Uani 1 1 d . . . . .
H10A H 0.5409 0.6479 0.3700 0.028 Uiso 1 1 calc R U . . .
H10B H 0.4236 0.4838 0.4012 0.028 Uiso 1 1 calc R U . . .
C11 C 0.4775(3) 0.4208(2) 0.31207(7) 0.0258(3) Uani 1 1 d . . . . .
H11A H 0.4522 0.3001 0.3163 0.031 Uiso 1 1 calc R U . . .
H11B H 0.6138 0.4539 0.2859 0.031 Uiso 1 1 calc R U . . .
C12 C 0.2436(3) 0.4425(2) 0.28411(7) 0.0244(3) Uani 1 1 d . . . . .
H12A H 0.1148 0.4269 0.3130 0.029 Uiso 1 1 calc R U . . .
H12B H 0.2775 0.5593 0.2746 0.029 Uiso 1 1 calc R U . . .
C13 C 0.1513(3) 0.3153(2) 0.22806(7) 0.0262(3) Uani 1 1 d . . . . .
H13A H 0.1105 0.1977 0.2371 0.031 Uiso 1 1 calc R U . . .
H13B H 0.0035 0.3338 0.2114 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2762(3) 0.2300(2) 0.13154(7) 0.0251(3) Uani 1 1 d . . . . .
H14 H 0.1303 0.2490 0.1131 0.030 Uiso 1 1 calc R U . . .
C15 C 0.2251(3) 0.0398(2) 0.13816(7) 0.0255(3) Uani 1 1 d . . . . .
C16 C 0.3989(3) -0.0172(2) 0.16715(7) 0.0295(4) Uani 1 1 d . . . . .
H16 H 0.5459 0.0616 0.1832 0.035 Uiso 1 1 calc R U . . .
C17 C 0.3530(3) -0.1922(2) 0.17211(8) 0.0329(4) Uani 1 1 d . . . . .
H17 H 0.4697 -0.2301 0.1913 0.040 Uiso 1 1 calc R U . . .
C18 C 0.1348(4) -0.3088(2) 0.14868(8) 0.0347(4) Uani 1 1 d . . . . .
H18 H 0.1042 -0.4256 0.1520 0.042 Uiso 1 1 calc R U . . .
C19 C -0.0388(4) -0.2523(2) 0.12026(9) 0.0402(5) Uani 1 1 d . . . . .
H19 H -0.1866 -0.3312 0.1047 0.048 Uiso 1 1 calc R U . . .
C20 C 0.0065(3) -0.0788(2) 0.11490(8) 0.0343(4) Uani 1 1 d . . . . .
H20 H -0.1107 -0.0419 0.0956 0.041 Uiso 1 1 calc R U . . .
C21 C 0.4956(3) 0.2766(2) 0.09138(7) 0.0267(3) Uani 1 1 d . . . . .
C22 C 0.6172(5) 0.2692(4) -0.00781(9) 0.0647(7) Uani 1 1 d . . . . .
H22A H 0.5483 0.2250 -0.0476 0.097 Uiso 1 1 calc R U . . .
H22B H 0.7322 0.2083 0.0018 0.097 Uiso 1 1 calc R U . . .
H22C H 0.7016 0.3903 -0.0054 0.097 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 C9 1.3456(18) . ?
O1 N1 1.4198(17) . ?
O2 C9 1.3259(19) . ?
O2 C10 1.4484(18) . ?
O3 C14 1.4107(18) . ?
O3 C13 1.4383(19) . ?
O4 C21 1.197(2) . ?
O5 C21 1.328(2) . ?
O5 C22 1.457(2) . ?
N1 C7 1.3183(18) . ?
C1 C2 1.385(2) . ?
C1 C6 1.395(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.473(2) . ?
C7 C8 1.419(2) . ?
C8 C9 1.353(2) . ?
C8 H8 0.9300 . ?
C10 C11 1.507(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.524(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.511(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.520(2) . ?
C14 C21 1.526(2) . ?
C14 H14 0.9800 . ?
C15 C20 1.383(2) . ?
C15 C16 1.393(2) . ?
C16 C17 1.393(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C9 O1 N1 107.78(11) . . ?
C9 O2 C10 114.33(11) . . ?
C14 O3 C13 112.44(12) . . ?
C21 O5 C22 114.60(16) . . ?
C7 N1 O1 104.82(12) . . ?
C2 C1 C6 120.12(15) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.48(15) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.60(15) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.21(15) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.34(15) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.23(14) . . ?
C1 C6 C7 120.56(14) . . ?
C5 C6 C7 120.19(13) . . ?
N1 C7 C8 112.84(13) . . ?
N1 C7 C6 118.77(13) . . ?
C8 C7 C6 128.39(13) . . ?
C9 C8 C7 102.89(13) . . ?
C9 C8 H8 128.6 . . ?
C7 C8 H8 128.6 . . ?
O2 C9 O1 112.36(12) . . ?
O2 C9 C8 135.97(14) . . ?
O1 C9 C8 111.67(13) . . ?
O2 C10 C11 107.53(12) . . ?
O2 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
O2 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 C12 111.21(12) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 112.58(12) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
O3 C13 C12 107.89(13) . . ?
O3 C13 H13A 110.1 . . ?
C12 C13 H13A 110.1 . . ?
O3 C13 H13B 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
O3 C14 C15 113.48(13) . . ?
O3 C14 C21 106.34(13) . . ?
C15 C14 C21 107.87(12) . . ?
O3 C14 H14 109.7 . . ?
C15 C14 H14 109.7 . . ?
C21 C14 H14 109.7 . . ?
C20 C15 C16 119.24(16) . . ?
C20 C15 C14 120.36(15) . . ?
C16 C15 C14 120.39(15) . . ?
C17 C16 C15 120.13(16) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.97(17) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.00(17) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.26(17) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.38(17) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
O4 C21 O5 123.59(16) . . ?
O4 C21 C14 125.63(15) . . ?
O5 C21 C14 110.65(14) . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.043

_shelxl_version_number           2014/6




_publcif_funding_html            
;
;
