# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_338_b_reduced1_a
_database_code_depnum_ccdc_archive 'CCDC 2344514'
loop_
_audit_author_name
_audit_author_address
'Kishorkumar Sindogi'
;Indian Institute of Science
India
;
_audit_update_record             
;
2024-03-30 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H25 N O6'
_chemical_formula_weight         423.45

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      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                   7.8789(9)
_cell_length_b                   14.2204(13)
_cell_length_c                   10.1298(19)
_cell_angle_alpha                90
_cell_angle_beta                 110.174(7)
_cell_angle_gamma                90
_cell_volume                     1065.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      2.7526
_cell_measurement_theta_max      30.5421

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71076
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37464
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.105
_diffrn_reflns_theta_max         30.564
_diffrn_reflns_theta_full        25.243
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6437
_reflns_number_gt                6269
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.988

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0591P)²+0.0875P] 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 2814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6437
_refine_ls_number_parameters     284
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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
O2 O 0.51079(15) 0.51461(8) -0.04108(11) 0.0163(2) Uani 1 1 d . . . . .
O3 O 0.69444(15) 0.67789(8) 0.09810(11) 0.0149(2) Uani 1 1 d . . . . .
O4 O 0.24600(16) 0.49733(9) 0.08434(12) 0.0206(2) Uani 1 1 d . . . . .
O5 O 0.73146(16) 0.44477(8) 0.13429(12) 0.0187(2) Uani 1 1 d . . . . .
O6 O 0.44018(16) 0.72507(8) 0.13397(13) 0.0183(2) Uani 1 1 d . . . . .
O1 O 0.31344(15) 0.57903(9) 0.28530(13) 0.0188(2) Uani 1 1 d . . . . .
N1 N 0.76602(17) 0.63442(9) 0.38941(13) 0.0127(2) Uani 1 1 d . . . . .
C1 C 0.88393(19) 0.63725(11) 0.52741(15) 0.0133(3) Uani 1 1 d . . . . .
C2 C 0.90653(19) 0.56078(11) 0.62033(16) 0.0142(3) Uani 1 1 d . . . . .
C3 C 1.0261(2) 0.57205(12) 0.75990(16) 0.0189(3) Uani 1 1 d . . . . .
H3 H 1.043760 0.521627 0.824795 0.023 Uiso 1 1 calc R U . . .
C4 C 1.1170(2) 0.65529(13) 0.80278(17) 0.0208(3) Uani 1 1 d . . . . .
H4 H 1.196838 0.661550 0.897151 0.025 Uiso 1 1 calc R U . . .
C5 C 1.0943(2) 0.73105(13) 0.70994(17) 0.0203(3) Uani 1 1 d . . . . .
H5 H 1.157981 0.788202 0.741082 0.024 Uiso 1 1 calc R U . . .
C6 C 0.9785(2) 0.72193(11) 0.57271(17) 0.0171(3) Uani 1 1 d . . . . .
H6 H 0.962742 0.772844 0.508856 0.021 Uiso 1 1 calc R U . . .
C7 C 0.80536(19) 0.47566(11) 0.56728(15) 0.0139(3) Uani 1 1 d . . . . .
C8 C 0.68692(19) 0.47394(10) 0.42608(15) 0.0124(2) Uani 1 1 d . . . . .
C9 C 0.67465(18) 0.55805(10) 0.34255(14) 0.0115(2) Uani 1 1 d . . . . .
C10 C 0.5857(2) 0.39188(11) 0.37334(16) 0.0145(3) Uani 1 1 d . . . . .
H10 H 0.507152 0.390637 0.278067 0.017 Uiso 1 1 calc R U . . .
C11 C 0.5973(2) 0.31321(11) 0.45621(18) 0.0168(3) Uani 1 1 d . . . . .
C12 C 0.7145(2) 0.31618(11) 0.59638(17) 0.0195(3) Uani 1 1 d . . . . .
H12 H 0.723101 0.263066 0.655205 0.023 Uiso 1 1 calc R U . . .
C13 C 0.8171(2) 0.39440(12) 0.65015(16) 0.0175(3) Uani 1 1 d . . . . .
H13 H 0.897496 0.393877 0.744862 0.021 Uiso 1 1 calc R U . . .
C14 C 0.54626(18) 0.56405(10) 0.18957(14) 0.0112(2) Uani 1 1 d . . . . .
C15 C 0.3495(2) 0.54213(10) 0.17750(16) 0.0134(3) Uani 1 1 d . . . . .
C16 C 0.1338(2) 0.55911(13) 0.2913(2) 0.0235(3) Uani 1 1 d . . . . .
H16A H 0.042324 0.564042 0.195804 0.028 Uiso 1 1 calc R U . . .
H16B H 0.104100 0.606220 0.351974 0.028 Uiso 1 1 calc R U . . .
C17 C 0.1277(2) 0.46206(14) 0.34893(17) 0.0219(3) Uani 1 1 d . . . . .
H17A H 0.012139 0.453141 0.363648 0.033 Uiso 1 1 calc R U . . .
H17B H 0.227199 0.454817 0.438682 0.033 Uiso 1 1 calc R U . . .
H17C H 0.139643 0.415049 0.281945 0.033 Uiso 1 1 calc R U . . .
C18 C 0.4883(3) 0.22665(12) 0.3961(2) 0.0240(3) Uani 1 1 d . . . . .
H18A H 0.512568 0.178252 0.469123 0.036 Uiso 1 1 calc R U . . .
H18B H 0.522124 0.202923 0.317704 0.036 Uiso 1 1 calc R U . . .
H18C H 0.359312 0.242366 0.362143 0.036 Uiso 1 1 calc R U . . .
C19 C 0.60802(19) 0.49916(10) 0.09274(15) 0.0124(2) Uani 1 1 d . . . . .
C20 C 0.5721(2) 0.46623(12) -0.14340(16) 0.0180(3) Uani 1 1 d . . . . .
H20A H 0.599809 0.399634 -0.115903 0.022 Uiso 1 1 calc R U . . .
H20B H 0.682811 0.496486 -0.148551 0.022 Uiso 1 1 calc R U . . .
C21 C 0.4219(2) 0.47237(13) -0.28331(16) 0.0208(3) Uani 1 1 d . . . . .
H21A H 0.463027 0.446077 -0.356532 0.031 Uiso 1 1 calc R U . . .
H21B H 0.387638 0.538345 -0.304978 0.031 Uiso 1 1 calc R U . . .
H21C H 0.317225 0.436700 -0.279649 0.031 Uiso 1 1 calc R U . . .
C22 C 0.5517(2) 0.66642(10) 0.13843(14) 0.0131(3) Uani 1 1 d . . . . .
C23 C 0.7222(2) 0.77235(11) 0.05443(19) 0.0211(3) Uani 1 1 d . . . . .
H23A H 0.746688 0.816694 0.134177 0.025 Uiso 1 1 calc R U . . .
H23B H 0.613372 0.794005 -0.022821 0.025 Uiso 1 1 calc R U . . .
C24 C 0.8818(3) 0.76779(13) 0.0054(2) 0.0243(3) Uani 1 1 d . . . . .
H24A H 0.904707 0.830323 -0.025557 0.036 Uiso 1 1 calc R U . . .
H24B H 0.856084 0.723465 -0.073181 0.036 Uiso 1 1 calc R U . . .
H24C H 0.988694 0.746611 0.082929 0.036 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
O2 C19 1.3253(17) . ?
O2 C20 1.4582(18) . ?
O3 C22 1.3323(18) . ?
O3 C23 1.4542(18) . ?
O4 C15 1.1961(19) . ?
O5 C19 1.1995(18) . ?
O6 C22 1.2010(19) . ?
O1 C15 1.3275(19) . ?
O1 C16 1.4650(19) . ?
N1 C9 1.2989(19) . ?
N1 C1 1.3867(18) . ?
C1 C6 1.407(2) . ?
C1 C2 1.409(2) . ?
C2 C3 1.412(2) . ?
C2 C7 1.447(2) . ?
C3 C4 1.374(2) . ?
C4 C5 1.400(3) . ?
C5 C6 1.381(2) . ?
C7 C13 1.412(2) . ?
C7 C8 1.4130(19) . ?
C8 C10 1.411(2) . ?
C8 C9 1.449(2) . ?
C9 C14 1.5333(19) . ?
C10 C11 1.383(2) . ?
C11 C12 1.402(2) . ?
C11 C18 1.504(2) . ?
C12 C13 1.372(2) . ?
C14 C19 1.543(2) . ?
C14 C15 1.544(2) . ?
C14 C22 1.5507(19) . ?
C16 C17 1.506(3) . ?
C20 C21 1.503(2) . ?
C23 C24 1.504(2) . ?

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
C19 O2 C20 115.63(12) . . ?
C22 O3 C23 115.98(12) . . ?
C15 O1 C16 116.21(13) . . ?
C9 N1 C1 119.13(13) . . ?
N1 C1 C6 116.67(13) . . ?
N1 C1 C2 122.51(13) . . ?
C6 C1 C2 120.80(13) . . ?
C1 C2 C3 117.93(14) . . ?
C1 C2 C7 118.10(13) . . ?
C3 C2 C7 123.96(14) . . ?
C4 C3 C2 120.62(15) . . ?
C3 C4 C5 121.22(14) . . ?
C6 C5 C4 119.40(15) . . ?
C5 C6 C1 120.02(15) . . ?
C13 C7 C8 118.19(14) . . ?
C13 C7 C2 123.29(13) . . ?
C8 C7 C2 118.51(13) . . ?
C10 C8 C7 119.18(13) . . ?
C10 C8 C9 123.13(13) . . ?
C7 C8 C9 117.68(12) . . ?
N1 C9 C8 124.04(13) . . ?
N1 C9 C14 114.34(12) . . ?
C8 C9 C14 121.60(12) . . ?
C11 C10 C8 121.94(14) . . ?
C10 C11 C12 118.22(14) . . ?
C10 C11 C18 120.47(15) . . ?
C12 C11 C18 121.30(15) . . ?
C13 C12 C11 121.23(14) . . ?
C12 C13 C7 121.21(14) . . ?
C9 C14 C19 111.50(11) . . ?
C9 C14 C15 111.29(11) . . ?
C19 C14 C15 110.92(11) . . ?
C9 C14 C22 107.77(11) . . ?
C19 C14 C22 107.34(11) . . ?
C15 C14 C22 107.80(11) . . ?
O4 C15 O1 125.35(14) . . ?
O4 C15 C14 124.23(14) . . ?
O1 C15 C14 110.41(12) . . ?
O1 C16 C17 110.74(14) . . ?
O5 C19 O2 125.34(13) . . ?
O5 C19 C14 123.92(13) . . ?
O2 C19 C14 110.69(12) . . ?
O2 C20 C21 107.26(12) . . ?
O6 C22 O3 125.98(14) . . ?
O6 C22 C14 124.08(13) . . ?
O3 C22 C14 109.93(12) . . ?
O3 C23 C24 106.95(13) . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.091


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Hexane'
