# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_tch167s
_database_code_depnum_ccdc_archive 'CCDC 2044133'
loop_
_audit_author_name
_audit_author_address
'ban xu'
;research fellow
Singapore
;
_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2023-09-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H30 N2 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         470.55
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   21.9827(6)
_cell_length_b                   9.9652(2)
_cell_length_c                   16.3300(7)
_cell_angle_alpha                90
_cell_angle_beta                 132.2994(10)
_cell_angle_gamma                90
_cell_volume                     2645.89(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      3.6595
_cell_measurement_theta_max      67.6439
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000

_exptl_absorpt_coefficient_mu    0.633
_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  0.68
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(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            48933
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_theta_min         3.66
_diffrn_reflns_theta_max         68.11
_diffrn_reflns_theta_full        68.11
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             4789
_reflns_number_gt                4609
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1141
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.077
_refine_ls_number_reflns         4789
_refine_ls_number_parameters     362
_refine_ls_number_restraints     283
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²+0.4838P] 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         0.203
_refine_diff_density_min         -0.273
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 2101 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(7)

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 0.79486(18) 0.7649(3) 0.3511(2) 0.0595(6) Uani d . . . 1.0 . .
H H1 0.792751 0.779329 0.40537 0.071 Uiso calc U . R 1.0 . .
C C2 0.86770(19) 0.7853(4) 0.3753(3) 0.0704(8) Uani d . . . 1.0 . .
H H2 0.914332 0.81285 0.445907 0.085 Uiso calc U . R 1.0 . .
C C3 0.8718(2) 0.7654(3) 0.2960(3) 0.0731(8) Uani d . . . 1.0 . .
H H3 0.921031 0.778391 0.312831 0.088 Uiso calc U . R 1.0 . .
C C4 0.8028(2) 0.7262(4) 0.1921(3) 0.0728(8) Uani d . . . 1.0 . .
H H4 0.805176 0.713174 0.13787 0.087 Uiso calc U . R 1.0 . .
C C5 0.72951(17) 0.7057(3) 0.1668(2) 0.0581(6) Uani d . . . 1.0 . .
H H5 0.682899 0.680188 0.095463 0.07 Uiso calc U . R 1.0 . .
C C6 0.72474(14) 0.7228(2) 0.2462(2) 0.0454(5) Uani d . . . 1.0 . .
C C7 0.64640(16) 0.6916(3) 0.2211(2) 0.0537(6) Uani d . . . 1.0 . .
H H7A 0.599979 0.696802 0.141881 0.064 Uiso calc U . R 1.0 . .
H H7B 0.63827 0.757548 0.256704 0.064 Uiso calc U . R 1.0 . .
C C8 0.65057(14) 0.5511(2) 0.2626(2) 0.0449(5) Uani d . . . 1.0 . .
H H8A 0.698091 0.546211 0.341422 0.054 Uiso calc U . R 1.0 . .
H H8B 0.658261 0.485977 0.226085 0.054 Uiso calc U . R 1.0 . .
C C9 0.57329(13) 0.5133(2) 0.24176(18) 0.0409(5) Uani d . . . 1.0 . .
C C10 0.50013(14) 0.5042(2) 0.12141(19) 0.0431(5) Uani d . . . 1.0 . .
C C11 0.58613(15) 0.3742(2) 0.2938(2) 0.0471(5) Uani d . . . 1.0 . .
C C12 0.5856(2) 0.1348(3) 0.2572(3) 0.0685(8) Uani d . . . 1.0 . .
C C13 0.5784(5) 0.0722(4) 0.1675(5) 0.145(3) Uani d . . . 1.0 . .
H H13A 0.533295 0.112295 0.097593 0.217 Uiso calc U . R 1.0 . .
H H13B 0.56887 -0.022405 0.16453 0.217 Uiso calc U . R 1.0 . .
H H13C 0.62842 0.086666 0.182839 0.217 Uiso calc U . R 1.0 . .
C C14 0.6669(3) 0.1001(5) 0.3715(4) 0.0977(12) Uani d . . . 1.0 . .
H H14A 0.672424 0.004325 0.379843 0.147 Uiso calc U . R 1.0 . .
H H14B 0.668197 0.137607 0.426836 0.147 Uiso calc U . R 1.0 . .
H H14C 0.711303 0.136332 0.380022 0.147 Uiso calc U . R 1.0 . .
C C15 0.5131(3) 0.1035(5) 0.2464(4) 0.1004(13) Uani d . . . 1.0 . .
H H15A 0.464431 0.14446 0.180395 0.151 Uiso calc U . R 1.0 . .
H H15B 0.523422 0.138097 0.309674 0.151 Uiso calc U . R 1.0 . .
H H15C 0.505542 0.008088 0.242439 0.151 Uiso calc U . R 1.0 . .
C C16 0.49632(15) 0.5955(3) 0.35980(19) 0.0461(5) Uani d . . . 1.0 . .
H H16A 0.519603 0.507948 0.392669 0.055 Uiso calc U . R 1.0 A 1
H H16B 0.442798 0.59977 0.337428 0.055 Uiso calc U . R 1.0 A 1
C C17 0.5506(8) 0.7008(13) 0.4458(11) 0.049(5) Uani d U P D 0.48(4) B 1
C C18 0.5429(14) 0.8375(15) 0.4323(13) 0.068(4) Uani d U P D 0.48(4) B 1
H H18 0.501257 0.871116 0.361333 0.082 Uiso calc U P R 0.48(4) B 1
C C19 0.5930(17) 0.9275(15) 0.5171(17) 0.077(4) Uani d U P D 0.48(4) B 1
H H19 0.584366 1.019472 0.504682 0.092 Uiso calc U P R 0.48(4) B 1
C C20 0.6568(12) 0.877(2) 0.6218(14) 0.070(3) Uani d U P D 0.48(4) B 1
H H20 0.692753 0.935593 0.680639 0.084 Uiso calc U P R 0.48(4) B 1
C C21 0.6672(9) 0.742(2) 0.6389(10) 0.073(3) Uani d U P D 0.48(4) B 1
H H21 0.708991 0.707912 0.709747 0.088 Uiso calc U P R 0.48(4) B 1
C C22 0.6152(10) 0.6538(16) 0.5500(11) 0.059(3) Uani d U P D 0.48(4) B 1
H H22 0.624409 0.561835 0.561698 0.071 Uiso calc U P R 0.48(4) B 1
C C17A 0.5526(7) 0.7014(11) 0.4484(10) 0.048(4) Uani d U P DG 0.52(4) B 2
C C18A 0.5231(8) 0.8323(13) 0.4190(10) 0.057(3) Uani d U P DG 0.52(4) B 2
H H18A 0.473263 0.850695 0.348346 0.069 Uiso calc U P R 0.52(4) B 2
C C19A 0.5682(11) 0.9356(10) 0.4953(14) 0.070(3) Uani d U P DG 0.52(4) B 2
H H19A 0.548481 1.023135 0.475665 0.084 Uiso calc U P R 0.52(4) B 2
C C20A 0.6428(8) 0.9081(16) 0.6010(14) 0.068(3) Uani d U P DG 0.52(4) B 2
H H20A 0.672918 0.977178 0.652012 0.082 Uiso calc U P R 0.52(4) B 2
C C21A 0.6723(6) 0.7772(19) 0.6304(11) 0.071(4) Uani d U P DG 0.52(4) B 2
H H21A 0.722139 0.758779 0.701042 0.086 Uiso calc U P R 0.52(4) B 2
C C22A 0.6272(9) 0.6739(13) 0.5541(11) 0.066(4) Uani d U P DG 0.52(4) B 2
H H22A 0.646922 0.586337 0.573725 0.079 Uiso calc U P R 0.52(4) B 2
C C23 0.43233(14) 0.7061(2) 0.18033(19) 0.0448(5) Uani d . . . 1.0 . .
C C24 0.34775(14) 0.7080(3) 0.14022(19) 0.0476(5) Uani d . . . 1.0 . .
C C25 0.31008(17) 0.8312(3) 0.1163(2) 0.0581(6) Uani d . . . 1.0 . .
H H25 0.337945 0.909438 0.127664 0.07 Uiso calc U . R 1.0 . .
C C26 0.23110(18) 0.8383(4) 0.0757(2) 0.0667(8) Uani d . . . 1.0 . .
H H26 0.206191 0.921377 0.060829 0.08 Uiso calc U . R 1.0 . .
C C27 0.18947(17) 0.7231(4) 0.0573(3) 0.0694(8) Uani d . . . 1.0 . .
H H27 0.136331 0.728131 0.030028 0.083 Uiso calc U . R 1.0 . .
C C28 0.22586(18) 0.6002(4) 0.0791(3) 0.0692(8) Uani d . . . 1.0 . .
H H28 0.196977 0.522246 0.065323 0.083 Uiso calc U . R 1.0 . .
C C29 0.30569(16) 0.5918(3) 0.1215(2) 0.0570(6) Uani d . . . 1.0 . .
H H29 0.33062 0.508534 0.137133 0.068 Uiso calc U . R 1.0 . .
N N1 0.44391(14) 0.4936(3) 0.02970(18) 0.0597(6) Uani d . . . 1.0 . .
N N2 0.48519(11) 0.6081(2) 0.26052(15) 0.0430(4) Uani d . . . 1.0 . .
O O1 0.58353(14) 0.28033(18) 0.23524(17) 0.0599(5) Uani d . . . 1.0 . .
O O2 0.59832(16) 0.3597(2) 0.37643(18) 0.0753(6) Uani d . . . 1.0 . .
O O3 0.56382(9) 0.61498(17) 0.29306(13) 0.0441(4) Uani d . . . 1.0 . .
O O4 0.45111(12) 0.7776(2) 0.14086(17) 0.0614(5) Uani d . . . 1.0 . .


_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 C2 . 1.382(4) ?
C1 C6 . 1.390(4) ?
C1 H1 . 0.93 ?
C2 C3 . 1.370(5) ?
C2 H2 . 0.93 ?
C3 C4 . 1.367(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.383(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.380(4) ?
C5 H5 . 0.93 ?
C6 C7 . 1.510(3) ?
C7 C8 . 1.531(3) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 C9 . 1.538(3) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 O3 . 1.416(3) ?
C9 C10 . 1.484(3) ?
C9 C11 . 1.550(3) ?
C10 N1 . 1.136(3) ?
C11 O2 . 1.195(3) ?
C11 O1 . 1.311(3) ?
C12 O1 . 1.487(3) ?
C12 C13 . 1.500(5) ?
C12 C15 . 1.512(6) ?
C12 C14 . 1.519(5) ?
C13 H13A . 0.96 ?
C13 H13B . 0.96 ?
C13 H13C . 0.96 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C16 N2 . 1.473(3) ?
C16 C17 . 1.498(12) ?
C16 C17A . 1.526(10) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 C22 . 1.371(8) ?
C17 C18 . 1.371(9) ?
C18 C19 . 1.373(10) ?
C18 H18 . 0.93 ?
C19 C20 . 1.383(11) ?
C19 H19 . 0.93 ?
C20 C21 . 1.367(11) ?
C20 H20 . 0.93 ?
C21 C22 . 1.395(10) ?
C21 H21 . 0.93 ?
C22 H22 . 0.93 ?
C17A C18A . 1.39 ?
C17A C22A . 1.39 ?
C18A C19A . 1.39 ?
C18A H18A . 0.93 ?
C19A C20A . 1.39 ?
C19A H19A . 0.93 ?
C20A C21A . 1.39 ?
C20A H20A . 0.93 ?
C21A C22A . 1.39 ?
C21A H21A . 0.93 ?
C22A H22A . 0.93 ?
C23 O4 . 1.205(3) ?
C23 N2 . 1.403(3) ?
C23 C24 . 1.499(3) ?
C24 C29 . 1.382(4) ?
C24 C25 . 1.383(4) ?
C25 C26 . 1.382(4) ?
C25 H25 . 0.93 ?
C26 C27 . 1.370(5) ?
C26 H26 . 0.93 ?
C27 C28 . 1.372(5) ?
C27 H27 . 0.93 ?
C28 C29 . 1.389(4) ?
C28 H28 . 0.93 ?
C29 H29 . 0.93 ?
N2 O3 . 1.428(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
C2 C1 C6 . . 120.5(3) ?
C2 C1 H1 . . 119.7 ?
C6 C1 H1 . . 119.7 ?
C3 C2 C1 . . 120.5(3) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C4 C3 C2 . . 119.4(3) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C5 . . 120.5(3) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 120.8(3) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C1 . . 118.2(2) ?
C5 C6 C7 . . 120.9(2) ?
C1 C6 C7 . . 120.8(2) ?
C6 C7 C8 . . 110.5(2) ?
C6 C7 H7A . . 109.5 ?
C8 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
C8 C7 H7B . . 109.5 ?
H7A C7 H7B . . 108.1 ?
C7 C8 C9 . . 113.43(19) ?
C7 C8 H8A . . 108.9 ?
C9 C8 H8A . . 108.9 ?
C7 C8 H8B . . 108.9 ?
C9 C8 H8B . . 108.9 ?
H8A C8 H8B . . 107.7 ?
O3 C9 C10 . . 111.56(17) ?
O3 C9 C8 . . 105.92(18) ?
C10 C9 C8 . . 111.03(19) ?
O3 C9 C11 . . 111.17(18) ?
C10 C9 C11 . . 107.83(18) ?
C8 C9 C11 . . 109.33(18) ?
N1 C10 C9 . . 178.1(3) ?
O2 C11 O1 . . 127.2(2) ?
O2 C11 C9 . . 123.1(2) ?
O1 C11 C9 . . 109.67(19) ?
O1 C12 C13 . . 101.8(3) ?
O1 C12 C15 . . 108.4(3) ?
C13 C12 C15 . . 113.0(4) ?
O1 C12 C14 . . 109.8(3) ?
C13 C12 C14 . . 111.6(4) ?
C15 C12 C14 . . 111.8(3) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C12 C15 H15A . . 109.5 ?
C12 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C12 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N2 C16 C17 . . 114.2(6) ?
N2 C16 C17A . . 114.3(6) ?
N2 C16 H16A . . 108.7 ?
C17 C16 H16A . . 108.7 ?
N2 C16 H16B . . 108.7 ?
C17 C16 H16B . . 108.7 ?
H16A C16 H16B . . 107.6 ?
C22 C17 C18 . . 116.9(7) ?
C22 C17 C16 . . 115.5(10) ?
C18 C17 C16 . . 127.7(11) ?
C17 C18 C19 . . 123.9(8) ?
C17 C18 H18 . . 118.0 ?
C19 C18 H18 . . 118.0 ?
C18 C19 C20 . . 117.9(8) ?
C18 C19 H19 . . 121.1 ?
C20 C19 H19 . . 121.1 ?
C21 C20 C19 . . 120.1(7) ?
C21 C20 H20 . . 119.9 ?
C19 C20 H20 . . 119.9 ?
C20 C21 C22 . . 120.0(8) ?
C20 C21 H21 . . 120.0 ?
C22 C21 H21 . . 120.0 ?
C17 C22 C21 . . 121.1(9) ?
C17 C22 H22 . . 119.5 ?
C21 C22 H22 . . 119.5 ?
C18A C17A C22A . . 120.0 ?
C18A C17A C16 . . 115.4(8) ?
C22A C17A C16 . . 124.5(8) ?
C17A C18A C19A . . 120.0 ?
C17A C18A H18A . . 120.0 ?
C19A C18A H18A . . 120.0 ?
C20A C19A C18A . . 120.0 ?
C20A C19A H19A . . 120.0 ?
C18A C19A H19A . . 120.0 ?
C19A C20A C21A . . 120.0 ?
C19A C20A H20A . . 120.0 ?
C21A C20A H20A . . 120.0 ?
C22A C21A C20A . . 120.0 ?
C22A C21A H21A . . 120.0 ?
C20A C21A H21A . . 120.0 ?
C21A C22A C17A . . 120.0 ?
C21A C22A H22A . . 120.0 ?
C17A C22A H22A . . 120.0 ?
O4 C23 N2 . . 122.9(2) ?
O4 C23 C24 . . 122.0(2) ?
N2 C23 C24 . . 114.9(2) ?
C29 C24 C25 . . 119.8(2) ?
C29 C24 C23 . . 122.3(2) ?
C25 C24 C23 . . 117.8(2) ?
C26 C25 C24 . . 120.1(3) ?
C26 C25 H25 . . 119.9 ?
C24 C25 H25 . . 119.9 ?
C27 C26 C25 . . 120.0(3) ?
C27 C26 H26 . . 120.0 ?
C25 C26 H26 . . 120.0 ?
C26 C27 C28 . . 120.3(3) ?
C26 C27 H27 . . 119.9 ?
C28 C27 H27 . . 119.9 ?
C27 C28 C29 . . 120.2(3) ?
C27 C28 H28 . . 119.9 ?
C29 C28 H28 . . 119.9 ?
C24 C29 C28 . . 119.5(3) ?
C24 C29 H29 . . 120.3 ?
C28 C29 H29 . . 120.3 ?
C23 N2 O3 . . 110.41(17) ?
C23 N2 C16 . . 120.41(18) ?
O3 N2 C16 . . 109.38(16) ?
C11 O1 C12 . . 122.7(2) ?
C9 O3 N2 . . 111.63(15) ?

####################################################################### 
# 
# 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_tch192s
_database_code_depnum_ccdc_archive 'CCDC 2059577'
loop_
_audit_author_name
_audit_author_address
'Dr Yongxin Li'
;research fellow
Singapore
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2023-09-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H13 N O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         239.22
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_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                   6.7311(4)
_cell_length_b                   6.8135(3)
_cell_length_c                   24.7073(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1133.13(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5558
_cell_measurement_theta_min      3.5778
_cell_measurement_theta_max      68.1523
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504

_exptl_absorpt_coefficient_mu    0.950
_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  0.72
_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            6718
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         68.15
_diffrn_reflns_theta_full        68.15
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             2031
_reflns_number_gt                1996
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0774
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_number_reflns         2031
_refine_ls_number_parameters     157
_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)+(0.0333P)²+0.2429P] 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         0.169
_refine_diff_density_min         -0.213
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 789 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)

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 0.4802(3) 0.6158(3) 0.48884(7) 0.0128(4) Uani d . . . 1 . .
C C2 0.5188(3) 0.5334(3) 0.43190(7) 0.0133(4) Uani d . . . 1 . .
C C3 0.3192(3) 0.5181(3) 0.40280(7) 0.0171(4) Uani d . . . 1 . .
H H3A 0.262663 0.64957 0.39821 0.026 Uiso calc U . R 1 . .
H H3B 0.22815 0.437304 0.424296 0.026 Uiso calc U . R 1 . .
H H3C 0.338654 0.457478 0.367216 0.026 Uiso calc U . R 1 . .
C C4 0.6137(3) 0.3297(3) 0.43875(7) 0.0130(4) Uani d . . . 1 . .
C C5 0.6844(3) 0.6527(3) 0.35130(7) 0.0147(4) Uani d . . . 1 . .
C C6 0.5863(3) 0.7828(3) 0.31725(8) 0.0192(4) Uani d . . . 1 . .
H H6 0.493849 0.874395 0.331602 0.023 Uiso calc U . R 1 . .
C C7 0.6245(3) 0.7776(3) 0.26205(8) 0.0195(4) Uani d . . . 1 . .
H H7 0.557285 0.865593 0.238503 0.023 Uiso calc U . R 1 . .
C C8 0.7607(3) 0.6444(3) 0.24107(8) 0.0162(4) Uani d . . . 1 . .
C C9 0.8606(3) 0.5171(3) 0.27533(8) 0.0176(4) Uani d . . . 1 . .
H H9 0.955594 0.427644 0.261155 0.021 Uiso calc U . R 1 . .
C C10 0.8209(3) 0.5211(3) 0.33084(8) 0.0173(4) Uani d . . . 1 . .
H H10 0.887807 0.433164 0.354473 0.021 Uiso calc U . R 1 . .
C C11 0.9309(4) 0.5241(3) 0.16283(8) 0.0262(5) Uani d . . . 1 . .
H H11A 1.063417 0.557792 0.17641 0.039 Uiso calc U . R 1 . .
H H11B 0.928624 0.537653 0.123344 0.039 Uiso calc U . R 1 . .
H H11C 0.899324 0.388358 0.172706 0.039 Uiso calc U . R 1 . .
N N1 0.4850(3) 0.8085(2) 0.49374(6) 0.0153(3) Uani d . . . 1 . .
H H1A 0.4571 0.863576 0.525046 0.018 Uiso calc U . R 1 . .
H H1B 0.516155 0.881974 0.465707 0.018 Uiso calc U . R 1 . .
O O1 0.4375(2) 0.5053(2) 0.52679(5) 0.0167(3) Uani d . . . 1 . .
O O2 0.8014(2) 0.3412(2) 0.45463(5) 0.0183(3) Uani d . . . 1 . .
H H2 0.843885 0.228205 0.461835 0.027 Uiso calc U . R 1 . .
O O3 0.5231(2) 0.17915(19) 0.43149(6) 0.0206(3) Uani d . . . 1 . .
O O4 0.6545(2) 0.66864(18) 0.40715(5) 0.0147(3) Uani d . . . 1 . .
O O5 0.7874(2) 0.6531(2) 0.18616(5) 0.0214(3) 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 O1 . 1.236(2) ?
C1 N1 . 1.319(2) ?
C1 C2 . 1.537(2) ?
C2 O4 . 1.434(2) ?
C2 C3 . 1.528(3) ?
C2 C4 . 1.537(2) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 O3 . 1.207(2) ?
C4 O2 . 1.326(2) ?
C5 C10 . 1.380(3) ?
C5 C6 . 1.389(3) ?
C5 O4 . 1.399(2) ?
C6 C7 . 1.388(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.390(3) ?
C7 H7 . 0.95 ?
C8 O5 . 1.370(2) ?
C8 C9 . 1.386(3) ?
C9 C10 . 1.398(3) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?
C11 O5 . 1.427(3) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
N1 H1A . 0.88 ?
N1 H1B . 0.88 ?
O2 H2 . 0.84 ?

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
O1 C1 N1 . . 122.83(18) ?
O1 C1 C2 . . 120.76(16) ?
N1 C1 C2 . . 116.32(16) ?
O4 C2 C3 . . 113.79(14) ?
O4 C2 C4 . . 111.27(15) ?
C3 C2 C4 . . 110.82(15) ?
O4 C2 C1 . . 105.27(14) ?
C3 C2 C1 . . 107.88(16) ?
C4 C2 C1 . . 107.40(14) ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O3 C4 O2 . . 125.12(17) ?
O3 C4 C2 . . 122.79(17) ?
O2 C4 C2 . . 112.07(15) ?
C10 C5 C6 . . 120.63(17) ?
C10 C5 O4 . . 120.51(17) ?
C6 C5 O4 . . 118.65(17) ?
C7 C6 C5 . . 119.38(19) ?
C7 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
C6 C7 C8 . . 120.34(19) ?
C6 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
O5 C8 C9 . . 124.59(18) ?
O5 C8 C7 . . 115.35(18) ?
C9 C8 C7 . . 120.06(18) ?
C8 C9 C10 . . 119.61(19) ?
C8 C9 H9 . . 120.2 ?
C10 C9 H9 . . 120.2 ?
C5 C10 C9 . . 119.96(18) ?
C5 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
O5 C11 H11A . . 109.5 ?
O5 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O5 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C1 N1 H1A . . 120.0 ?
C1 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
C4 O2 H2 . . 109.5 ?
C5 O4 C2 . . 117.56(13) ?
C8 O5 C11 . . 117.56(16) ?

