# 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_rb132s
_database_code_depnum_ccdc_archive 'CCDC 2292753'
loop_
_audit_author_name
_audit_author_address
'Yongxin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N2 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         308.29
_chemical_absolute_configuration unk

_chemical_melting_point          372-375

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   6.1315(4)
_cell_length_b                   10.3380(7)
_cell_length_c                   23.2076(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1471.07(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9632
_cell_measurement_theta_min      4.6826
_cell_measurement_theta_max      67.5678
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648

_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.83

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10874
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_theta_min         3.81
_diffrn_reflns_theta_max         67.56
_diffrn_reflns_theta_full        67.56
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27

_refine_special_details          
;

Refined as a 2-component inversion twin.
;

_reflns_number_total             2610
_reflns_number_gt                2565
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0892
_refine_ls_goodness_of_fit_ref   1.534
_refine_ls_restrained_S_all      1.534
_refine_ls_number_reflns         2610
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(2)

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5321(4) 0.2602(2) 0.25553(9) 0.0318(5) Uani d . . . 1 . .
H H1A 0.582464 0.191486 0.281384 0.048 Uiso calc U . R 1 . .
H H1B 0.572551 0.238921 0.215796 0.048 Uiso calc U . R 1 . .
H H1C 0.373173 0.268169 0.258347 0.048 Uiso calc U . R 1 . .
C C2 0.8493(3) 0.37688(19) 0.27845(7) 0.0221(4) Uani d . . . 1 . .
C C3 0.9415(4) 0.50728(18) 0.29362(8) 0.0254(4) Uani d . . . 1 . .
H H3A 0.904804 0.569305 0.262598 0.031 Uiso calc U . R 1 . .
H H3B 1.102391 0.500764 0.295653 0.031 Uiso calc U . R 1 . .
C C4 0.8563(3) 0.55938(17) 0.35061(8) 0.0216(4) Uani d . . . 1 . .
H H4 0.693369 0.563093 0.349592 0.026 Uiso calc U . R 1 . .
C C5 0.9467(4) 0.69168(19) 0.36540(8) 0.0295(5) Uani d . . . 1 . .
H H5A 0.889659 0.756334 0.337782 0.035 Uiso calc U . R 1 . .
H H5B 1.107652 0.690285 0.361957 0.035 Uiso calc U . R 1 . .
C C6 0.8832(4) 0.73083(19) 0.42662(8) 0.0282(4) Uani d . . . 1 . .
H H6A 0.959123 0.811866 0.4373 0.034 Uiso calc U . R 1 . .
H H6B 0.724119 0.746659 0.428546 0.034 Uiso calc U . R 1 . .
C C7 0.9449(3) 0.62425(18) 0.46848(8) 0.0244(4) Uani d . . . 1 . .
H H7A 1.105674 0.617611 0.471132 0.029 Uiso calc U . R 1 . .
H H7B 0.88737 0.644687 0.507282 0.029 Uiso calc U . R 1 . .
C C8 0.6663(3) 0.44988(17) 0.46817(8) 0.0202(4) Uani d . . . 1 . .
C C9 0.5873(3) 0.33004(17) 0.43804(8) 0.0191(4) Uani d . . . 1 . .
C C10 0.3773(3) 0.33086(18) 0.41488(8) 0.0234(4) Uani d . . . 1 . .
H H10 0.293853 0.408282 0.415223 0.028 Uiso calc U . R 1 . .
C C11 0.2901(3) 0.21876(18) 0.39135(8) 0.0229(4) Uani d . . . 1 . .
H H11 0.149686 0.219012 0.374024 0.028 Uiso calc U . R 1 . .
C C12 0.4125(3) 0.10708(18) 0.39381(7) 0.0201(4) Uani d . . . 1 . .
C C13 0.6220(3) 0.10369(18) 0.41655(8) 0.0219(4) Uani d . . . 1 . .
H H13 0.703288 0.025462 0.417173 0.026 Uiso calc U . R 1 . .
C C14 0.7095(3) 0.21711(18) 0.43827(7) 0.0212(4) Uani d . . . 1 . .
H H14 0.853487 0.217602 0.453378 0.025 Uiso calc U . R 1 . .
N N1 0.8547(3) 0.50220(15) 0.44858(7) 0.0218(4) Uani d . . . 1 . .
N N2 0.3166(3) -0.01318(16) 0.37140(6) 0.0238(4) Uani d . . . 1 . .
O O1 0.9552(2) 0.28025(13) 0.27267(6) 0.0291(3) Uani d . . . 1 . .
O O2 0.6322(2) 0.38097(13) 0.27180(6) 0.0283(3) Uani d . . . 1 . .
O O3 0.9264(2) 0.46507(12) 0.39343(5) 0.0202(3) Uani d . . . 1 . .
O O4 0.5739(3) 0.49174(13) 0.51090(6) 0.0296(4) Uani d . . . 1 . .
O O5 0.4173(3) -0.11423(13) 0.37867(6) 0.0330(4) Uani d . . . 1 . .
O O6 0.1398(3) -0.00648(14) 0.34687(6) 0.0319(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 . 1.441(3) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 O1 . 1.199(3) ?
C2 O2 . 1.341(3) ?
C2 C3 . 1.504(3) ?
C3 C4 . 1.521(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 O3 . 1.457(2) ?
C4 C5 . 1.515(3) ?
C4 H4 . 1.0 ?
C5 C6 . 1.528(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.517(3) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 N1 . 1.453(2) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 O4 . 1.221(2) ?
C8 N1 . 1.354(3) ?
C8 C9 . 1.503(2) ?
C9 C14 . 1.387(3) ?
C9 C10 . 1.395(3) ?
C10 C11 . 1.388(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.378(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.389(3) ?
C12 N2 . 1.470(2) ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
N1 O3 . 1.407(2) ?
N2 O5 . 1.225(2) ?
N2 O6 . 1.227(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 H1A . . 109.5 ?
O2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 O2 . . 123.46(18) ?
O1 C2 C3 . . 124.70(18) ?
O2 C2 C3 . . 111.84(17) ?
C2 C3 C4 . . 113.08(15) ?
C2 C3 H3A . . 109.0 ?
C4 C3 H3A . . 109.0 ?
C2 C3 H3B . . 109.0 ?
C4 C3 H3B . . 109.0 ?
H3A C3 H3B . . 107.8 ?
O3 C4 C5 . . 109.97(15) ?
O3 C4 C3 . . 104.76(14) ?
C5 C4 C3 . . 113.03(16) ?
O3 C4 H4 . . 109.7 ?
C5 C4 H4 . . 109.7 ?
C3 C4 H4 . . 109.7 ?
C4 C5 C6 . . 110.89(17) ?
C4 C5 H5A . . 109.5 ?
C6 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
C6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
C7 C6 C5 . . 109.85(16) ?
C7 C6 H6A . . 109.7 ?
C5 C6 H6A . . 109.7 ?
C7 C6 H6B . . 109.7 ?
C5 C6 H6B . . 109.7 ?
H6A C6 H6B . . 108.2 ?
N1 C7 C6 . . 109.41(15) ?
N1 C7 H7A . . 109.8 ?
C6 C7 H7A . . 109.8 ?
N1 C7 H7B . . 109.8 ?
C6 C7 H7B . . 109.8 ?
H7A C7 H7B . . 108.2 ?
O4 C8 N1 . . 121.79(17) ?
O4 C8 C9 . . 121.35(16) ?
N1 C8 C9 . . 116.62(16) ?
C14 C9 C10 . . 120.33(16) ?
C14 C9 C8 . . 121.20(17) ?
C10 C9 C8 . . 118.14(16) ?
C11 C10 C9 . . 120.13(17) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C12 C11 C10 . . 118.23(16) ?
C12 C11 H11 . . 120.9 ?
C10 C11 H11 . . 120.9 ?
C11 C12 C13 . . 122.72(17) ?
C11 C12 N2 . . 118.41(16) ?
C13 C12 N2 . . 118.87(16) ?
C14 C13 C12 . . 118.37(17) ?
C14 C13 H13 . . 120.8 ?
C12 C13 H13 . . 120.8 ?
C13 C14 C9 . . 120.15(17) ?
C13 C14 H14 . . 119.9 ?
C9 C14 H14 . . 119.9 ?
C8 N1 O3 . . 117.58(14) ?
C8 N1 C7 . . 124.41(16) ?
O3 N1 C7 . . 114.02(14) ?
O5 N2 O6 . . 123.87(16) ?
O5 N2 C12 . . 118.10(15) ?
O6 N2 C12 . . 118.03(16) ?
C2 O2 C1 . . 115.19(16) ?
N1 O3 C4 . . 110.23(13) ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
