# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 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_029_002
_database_code_depnum_ccdc_archive 'CCDC 2151115'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;IBS KAIST
South Korea
;
_audit_update_record             
;
2022-02-09 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 N O6'
_chemical_formula_sum            'C18 H21 N O6'
_chemical_formula_weight         347.36

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                   8.1602(3)
_cell_length_b                   10.1021(4)
_cell_length_c                   11.5212(4)
_cell_angle_alpha                88.2151(14)
_cell_angle_beta                 69.4794(14)
_cell_angle_gamma                72.0806(13)
_cell_volume                     843.20(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9543
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5000
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\^I1/4S 3.0 Microfocus'
_diffrn_measurement_device_type  'PHOTON II 14'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20654
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.724
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3808
_reflns_number_gt                3238
_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       'Bruker APEXIII'
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0324P)²+0.2959P] 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         3808
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
C1 C 0.60228(18) 0.02987(13) 0.61302(12) 0.0259(3) Uani 1 1 d . . . . .
C2 C 0.7337(2) -0.08239(13) 0.53147(13) 0.0321(3) Uani 1 1 d . . . . .
H2 H 0.738618 -0.175011 0.551936 0.039 Uiso 1 1 calc R U . . .
C3 C 0.8574(2) -0.06041(14) 0.42077(13) 0.0335(3) Uani 1 1 d . . . . .
H3 H 0.943046 -0.137915 0.364165 0.040 Uiso 1 1 calc R U . . .
C4 C 0.85728(18) 0.07371(14) 0.39177(12) 0.0287(3) Uani 1 1 d . . . . .
H4 H 0.945322 0.086882 0.316371 0.034 Uiso 1 1 calc R U . . .
C5 C 0.73026(17) 0.18947(12) 0.47133(11) 0.0234(2) Uani 1 1 d . . . . .
C6 C 0.60147(17) 0.16412(12) 0.57868(11) 0.0231(2) Uani 1 1 d . . . . .
C7 C 0.4752(2) 0.00578(14) 0.73696(13) 0.0319(3) Uani 1 1 d . . . . .
H7A H 0.348366 0.029481 0.736413 0.038 Uiso 1 1 calc R U . . .
H7B H 0.516156 -0.093955 0.752129 0.038 Uiso 1 1 calc R U . . .
O8 O 0.47581(12) 0.09171(9) 0.83551(8) 0.0287(2) Uani 1 1 d . . . . .
O9 O 0.74661(14) -0.06103(10) 0.82787(9) 0.0350(2) Uani 1 1 d . . . . .
C10 C 0.63061(17) 0.05092(13) 0.86396(11) 0.0251(3) Uani 1 1 d . . . . .
C11 C 0.63678(18) 0.16384(13) 0.94221(12) 0.0277(3) Uani 1 1 d . . . . .
H11A H 0.522203 0.191679 1.016671 0.033 Uiso 1 1 calc R U . . .
H11B H 0.640564 0.246466 0.894091 0.033 Uiso 1 1 calc R U . . .
C12 C 0.80155(18) 0.12011(13) 0.98375(12) 0.0289(3) Uani 1 1 d . . . . .
H12A H 0.915632 0.083187 0.909932 0.035 Uiso 1 1 calc R U . . .
H12B H 0.791035 0.043874 1.039196 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8173(2) 0.24054(15) 1.05244(13) 0.0326(3) Uani 1 1 d . . . . .
H13A H 0.695100 0.289690 1.115631 0.039 Uiso 1 1 calc R U . . .
H13B H 0.903905 0.201757 1.096566 0.039 Uiso 1 1 calc R U . . .
C14 C 0.88334(19) 0.34351(14) 0.96730(12) 0.0295(3) Uani 1 1 d . . . . .
H14 H 1.005879 0.310805 0.908653 0.035 Uiso 1 1 calc R U . . .
C15 C 0.78837(19) 0.47520(14) 0.96554(12) 0.0313(3) Uani 1 1 d . . . . .
H15 H 0.665296 0.508878 1.023292 0.038 Uiso 1 1 calc R U . . .
C16 C 0.8598(2) 0.57562(14) 0.87943(13) 0.0329(3) Uani 1 1 d . . . . .
H16A H 0.996297 0.539120 0.844922 0.039 Uiso 1 1 calc R U . . .
H16B H 0.823794 0.666011 0.927590 0.039 Uiso 1 1 calc R U . . .
C17 C 0.78780(19) 0.60043(13) 0.77166(13) 0.0300(3) Uani 1 1 d . . . . .
H17A H 0.651333 0.629176 0.805425 0.036 Uiso 1 1 calc R U . . .
H17B H 0.824670 0.677270 0.725681 0.036 Uiso 1 1 calc R U . . .
C18 C 0.86233(17) 0.47056(12) 0.68322(12) 0.0258(3) Uani 1 1 d . . . . .
H18A H 0.997525 0.449013 0.642571 0.031 Uiso 1 1 calc R U . . .
H18B H 0.839677 0.391290 0.731873 0.031 Uiso 1 1 calc R U . . .
C19 C 0.77962(17) 0.48214(12) 0.58447(11) 0.0241(3) Uani 1 1 d . . . . .
O20 O 0.66648(14) 0.58315(9) 0.56909(9) 0.0326(2) Uani 1 1 d . . . . .
O21 O 0.84989(12) 0.35932(9) 0.51373(8) 0.0259(2) Uani 1 1 d . . . . .
C22 C 0.74661(18) 0.33209(13) 0.44244(11) 0.0261(3) Uani 1 1 d . . . . .
H22A H 0.812540 0.333800 0.352355 0.031 Uiso 1 1 calc R U . . .
H22B H 0.622945 0.403133 0.467130 0.031 Uiso 1 1 calc R U . . .
N23 N 0.45454(15) 0.28354(11) 0.66214(10) 0.0267(2) Uani 1 1 d . . . . .
O24 O 0.49956(14) 0.37216(10) 0.70193(10) 0.0405(3) Uani 1 1 d . . . . .
O25 O 0.29520(13) 0.28660(11) 0.68650(9) 0.0370(2) Uani 1 1 d . . . . .


_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
C1 C2 1.3894(19) . ?
C1 C6 1.3996(16) . ?
C1 C7 1.5065(18) . ?
C2 C3 1.383(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.3853(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3917(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3908(17) . ?
C5 C22 1.5039(16) . ?
C6 N23 1.4803(15) . ?
C7 O8 1.4530(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O8 C10 1.3545(15) . ?
O9 C10 1.2010(16) . ?
C10 C11 1.4992(17) . ?
C11 C12 1.5181(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5332(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.4985(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.3212(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.500(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.5336(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5123(17) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.4984(17) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O20 1.2036(15) . ?
C19 O21 1.3528(15) . ?
O21 C22 1.4500(14) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N23 O25 1.2208(14) . ?
N23 O24 1.2217(14) . ?

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
C2 C1 C6 117.44(12) . . ?
C2 C1 C7 120.46(11) . . ?
C6 C1 C7 121.98(12) . . ?
C3 C2 C1 120.55(12) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.53(12) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 121.04(12) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 116.97(11) . . ?
C6 C5 C22 123.63(11) . . ?
C4 C5 C22 119.26(11) . . ?
C5 C6 C1 123.32(11) . . ?
C5 C6 N23 119.36(10) . . ?
C1 C6 N23 117.31(11) . . ?
O8 C7 C1 109.95(10) . . ?
O8 C7 H7A 109.7 . . ?
C1 C7 H7A 109.7 . . ?
O8 C7 H7B 109.7 . . ?
C1 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C10 O8 C7 115.76(10) . . ?
O9 C10 O8 122.93(11) . . ?
O9 C10 C11 125.96(12) . . ?
O8 C10 C11 111.10(11) . . ?
C10 C11 C12 113.25(11) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 112.80(11) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 112.93(11) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 126.59(13) . . ?
C15 C14 H14 116.7 . . ?
C13 C14 H14 116.7 . . ?
C14 C15 C16 125.06(13) . . ?
C14 C15 H15 117.5 . . ?
C16 C15 H15 117.5 . . ?
C15 C16 C17 113.27(11) . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 111.53(11) . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 114.25(10) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
O20 C19 O21 123.96(11) . . ?
O20 C19 C18 126.48(11) . . ?
O21 C19 C18 109.56(10) . . ?
C19 O21 C22 117.81(9) . . ?
O21 C22 C5 105.82(9) . . ?
O21 C22 H22A 110.6 . . ?
C5 C22 H22A 110.6 . . ?
O21 C22 H22B 110.6 . . ?
C5 C22 H22B 110.6 . . ?
H22A C22 H22B 108.7 . . ?
O25 N23 O24 124.30(11) . . ?
O25 N23 C6 117.24(10) . . ?
O24 N23 C6 118.45(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.27(18) . . . . ?
C7 C1 C2 C3 -176.32(12) . . . . ?
C1 C2 C3 C4 2.7(2) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
C3 C4 C5 C6 -1.71(18) . . . . ?
C3 C4 C5 C22 174.11(11) . . . . ?
C4 C5 C6 C1 4.29(18) . . . . ?
C22 C5 C6 C1 -171.32(11) . . . . ?
C4 C5 C6 N23 -175.56(10) . . . . ?
C22 C5 C6 N23 8.83(17) . . . . ?
C2 C1 C6 C5 -3.33(18) . . . . ?
C7 C1 C6 C5 172.65(11) . . . . ?
C2 C1 C6 N23 176.52(10) . . . . ?
C7 C1 C6 N23 -7.50(17) . . . . ?
C2 C1 C7 O8 130.04(12) . . . . ?
C6 C1 C7 O8 -45.82(16) . . . . ?
C1 C7 O8 C10 -72.64(13) . . . . ?
C7 O8 C10 O9 -12.95(17) . . . . ?
C7 O8 C10 C11 165.87(10) . . . . ?
O9 C10 C11 C12 -4.94(18) . . . . ?
O8 C10 C11 C12 176.28(10) . . . . ?
C10 C11 C12 C13 174.21(11) . . . . ?
C11 C12 C13 C14 -73.95(15) . . . . ?
C12 C13 C14 C15 114.07(15) . . . . ?
C13 C14 C15 C16 179.47(12) . . . . ?
C14 C15 C16 C17 103.05(15) . . . . ?
C15 C16 C17 C18 -67.20(15) . . . . ?
C16 C17 C18 C19 172.92(11) . . . . ?
C17 C18 C19 O20 1.63(19) . . . . ?
C17 C18 C19 O21 -177.61(10) . . . . ?
O20 C19 O21 C22 -19.80(17) . . . . ?
C18 C19 O21 C22 159.46(10) . . . . ?
C19 O21 C22 C5 -129.73(11) . . . . ?
C6 C5 C22 O21 80.17(14) . . . . ?
C4 C5 C22 O21 -95.35(12) . . . . ?
C5 C6 N23 O25 124.69(12) . . . . ?
C1 C6 N23 O25 -55.16(15) . . . . ?
C5 C6 N23 O24 -55.24(16) . . . . ?
C1 C6 N23 O24 124.91(13) . . . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_026_014
_database_code_depnum_ccdc_archive 'CCDC 2151116'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;IBS KAIST
South Korea
;
_audit_update_record             
;
2022-02-09 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N O6'
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.30

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.9980(5)
_cell_length_b                   7.7936(3)
_cell_length_c                   15.3862(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.5061(12)
_cell_angle_gamma                90
_cell_volume                     1494.41(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.132
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6093
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\^I1/4S 3.0 Microfocus'
_diffrn_measurement_device_type  'PHOTON II 14'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25507
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.761
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3360
_reflns_number_gt                2920
_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       'Bruker APEXIII'
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0293P)²+0.5854P] 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         3360
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
C2 C 0.41976(10) 0.40275(18) 0.72851(8) 0.0321(3) Uani 1 1 d . . . . .
H2A H 0.434464 0.314418 0.776715 0.039 Uiso 1 1 calc R U . . .
H2B H 0.464166 0.504683 0.752607 0.039 Uiso 1 1 calc R U . . .
O3 O 0.30766(7) 0.44934(12) 0.70448(6) 0.0309(2) Uani 1 1 d . . . . .
O4 O 0.34086(8) 0.68451(13) 0.63174(7) 0.0380(2) Uani 1 1 d . . . . .
C5 C 0.27756(10) 0.59065(16) 0.65139(8) 0.0285(3) Uani 1 1 d . . . . .
C6 C 0.15720(10) 0.60711(18) 0.62434(9) 0.0331(3) Uani 1 1 d . . . . .
H6A H 0.134741 0.633057 0.679250 0.040 Uiso 1 1 calc R U . . .
H6B H 0.125583 0.494916 0.600783 0.040 Uiso 1 1 calc R U . . .
C7 C 0.11083(11) 0.74355(18) 0.55345(10) 0.0373(3) Uani 1 1 d . . . . .
H7A H 0.035580 0.764655 0.553036 0.045 Uiso 1 1 calc R U . . .
H7B H 0.151046 0.851413 0.572795 0.045 Uiso 1 1 calc R U . . .
C8 C 0.11195(10) 0.70544(17) 0.45782(9) 0.0338(3) Uani 1 1 d . . . . .
H8 H 0.085327 0.793816 0.414776 0.041 Uiso 1 1 calc R U . . .
C9 C 0.14520(10) 0.56491(16) 0.42603(9) 0.0297(3) Uani 1 1 d . . . . .
H9 H 0.169757 0.472590 0.466996 0.036 Uiso 1 1 calc R U . . .
C10 C 0.14685(10) 0.54106(17) 0.32917(8) 0.0313(3) Uani 1 1 d . . . . .
H10A H 0.221978 0.550629 0.326870 0.038 Uiso 1 1 calc R U . . .
H10B H 0.105737 0.635812 0.292322 0.038 Uiso 1 1 calc R U . . .
C11 C 0.10084(10) 0.37067(18) 0.28576(8) 0.0317(3) Uani 1 1 d . . . . .
H11A H 0.024274 0.365344 0.284337 0.038 Uiso 1 1 calc R U . . .
H11B H 0.103700 0.370646 0.222149 0.038 Uiso 1 1 calc R U . . .
C12 C 0.15507(10) 0.21043(17) 0.33088(8) 0.0288(3) Uani 1 1 d . . . . .
O13 O 0.11245(8) 0.07319(14) 0.32819(8) 0.0493(3) Uani 1 1 d . . . . .
O14 O 0.25965(6) 0.23647(11) 0.37387(5) 0.0261(2) Uani 1 1 d . . . . .
C15 C 0.31845(9) 0.09483(15) 0.42600(7) 0.0249(2) Uani 1 1 d . . . . .
H15A H 0.352958 0.024191 0.388697 0.030 Uiso 1 1 calc R U . . .
H15B H 0.270441 0.020952 0.449517 0.030 Uiso 1 1 calc R U . . .
C16 C 0.40115(9) 0.18018(14) 0.50226(7) 0.0221(2) Uani 1 1 d . . . . .
C17 C 0.49930(9) 0.22920(15) 0.49026(8) 0.0251(2) Uani 1 1 d . . . . .
H17 H 0.516738 0.194958 0.436893 0.030 Uiso 1 1 calc R U . . .
C18 C 0.57189(9) 0.32672(17) 0.55446(8) 0.0290(3) Uani 1 1 d . . . . .
H18 H 0.639351 0.355523 0.545887 0.035 Uiso 1 1 calc R U . . .
C19 C 0.54614(9) 0.38260(17) 0.63153(8) 0.0289(3) Uani 1 1 d . . . . .
H19 H 0.594643 0.454674 0.673769 0.035 Uiso 1 1 calc R U . . .
C20 C 0.45012(9) 0.33407(16) 0.64740(7) 0.0256(2) Uani 1 1 d . . . . .
C21 C 0.38155(9) 0.22852(15) 0.58355(7) 0.0227(2) Uani 1 1 d . . . . .
N22 N 0.28489(8) 0.16172(13) 0.60426(7) 0.0259(2) Uani 1 1 d . . . . .
O23 O 0.29935(8) 0.08160(13) 0.67533(6) 0.0368(2) Uani 1 1 d . . . . .
O24 O 0.19673(7) 0.18641(13) 0.55006(6) 0.0330(2) Uani 1 1 d . . . . .


_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
C2 O3 1.4442(15) . ?
C2 C20 1.5098(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O3 C5 1.3607(15) . ?
O4 C5 1.2020(16) . ?
C5 C6 1.5058(17) . ?
C6 C7 1.5199(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.505(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.3212(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.5081(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.5297(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5035(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O13 1.1999(16) . ?
C12 O14 1.3474(14) . ?
O14 C15 1.4483(14) . ?
C15 C16 1.5027(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.3934(16) . ?
C16 C21 1.3971(16) . ?
C17 C18 1.3835(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3903(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.3905(17) . ?
C19 H19 0.9500 . ?
C20 C21 1.3924(16) . ?
C21 N22 1.4760(15) . ?
N22 O24 1.2258(13) . ?
N22 O23 1.2264(13) . ?

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
O3 C2 C20 111.05(9) . . ?
O3 C2 H2A 109.4 . . ?
C20 C2 H2A 109.4 . . ?
O3 C2 H2B 109.4 . . ?
C20 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C5 O3 C2 117.01(10) . . ?
O4 C5 O3 122.89(12) . . ?
O4 C5 C6 127.61(12) . . ?
O3 C5 C6 109.50(10) . . ?
C5 C6 C7 115.28(11) . . ?
C5 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 C6 116.83(11) . . ?
C8 C7 H7A 108.1 . . ?
C6 C7 H7A 108.1 . . ?
C8 C7 H7B 108.1 . . ?
C6 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C9 C8 C7 128.35(12) . . ?
C9 C8 H8 115.8 . . ?
C7 C8 H8 115.8 . . ?
C8 C9 C10 124.47(12) . . ?
C8 C9 H9 117.8 . . ?
C10 C9 H9 117.8 . . ?
C9 C10 C11 115.14(11) . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C10 116.46(10) . . ?
C12 C11 H11A 108.2 . . ?
C10 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C10 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
O13 C12 O14 122.87(12) . . ?
O13 C12 C11 124.97(11) . . ?
O14 C12 C11 112.14(10) . . ?
C12 O14 C15 117.20(9) . . ?
O14 C15 C16 104.06(9) . . ?
O14 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
O14 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 109.0 . . ?
C17 C16 C21 116.84(10) . . ?
C17 C16 C15 119.78(10) . . ?
C21 C16 C15 123.12(10) . . ?
C18 C17 C16 121.35(11) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 120.03(11) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.67(11) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 117.61(11) . . ?
C19 C20 C2 120.47(11) . . ?
C21 C20 C2 121.83(11) . . ?
C20 C21 C16 123.22(11) . . ?
C20 C21 N22 118.01(10) . . ?
C16 C21 N22 118.76(10) . . ?
O24 N22 O23 124.29(10) . . ?
O24 N22 C21 119.10(9) . . ?
O23 N22 C21 116.60(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C20 C2 O3 C5 -70.74(14) . . . . ?
C2 O3 C5 O4 -7.22(17) . . . . ?
C2 O3 C5 C6 173.31(10) . . . . ?
O4 C5 C6 C7 9.41(19) . . . . ?
O3 C5 C6 C7 -171.16(11) . . . . ?
C5 C6 C7 C8 72.90(15) . . . . ?
C6 C7 C8 C9 2.4(2) . . . . ?
C7 C8 C9 C10 -177.68(12) . . . . ?
C8 C9 C10 C11 -133.35(13) . . . . ?
C9 C10 C11 C12 -59.87(15) . . . . ?
C10 C11 C12 O13 152.88(14) . . . . ?
C10 C11 C12 O14 -28.64(15) . . . . ?
O13 C12 O14 C15 -6.28(18) . . . . ?
C11 C12 O14 C15 175.21(10) . . . . ?
C12 O14 C15 C16 -148.68(10) . . . . ?
O14 C15 C16 C17 -87.00(12) . . . . ?
O14 C15 C16 C21 86.88(12) . . . . ?
C21 C16 C17 C18 -2.39(17) . . . . ?
C15 C16 C17 C18 171.86(11) . . . . ?
C16 C17 C18 C19 -2.10(19) . . . . ?
C17 C18 C19 C20 3.39(19) . . . . ?
C18 C19 C20 C21 -0.08(18) . . . . ?
C18 C19 C20 C2 -176.67(11) . . . . ?
O3 C2 C20 C19 137.72(12) . . . . ?
O3 C2 C20 C21 -38.72(16) . . . . ?
C19 C20 C21 C16 -4.73(17) . . . . ?
C2 C20 C21 C16 171.82(11) . . . . ?
C19 C20 C21 N22 173.79(10) . . . . ?
C2 C20 C21 N22 -9.66(17) . . . . ?
C17 C16 C21 C20 5.93(17) . . . . ?
C15 C16 C21 C20 -168.12(11) . . . . ?
C17 C16 C21 N22 -172.58(10) . . . . ?
C15 C16 C21 N22 13.38(16) . . . . ?
C20 C21 N22 O24 125.34(12) . . . . ?
C16 C21 N22 O24 -56.07(15) . . . . ?
C20 C21 N22 O23 -55.79(15) . . . . ?
C16 C21 N22 O23 122.80(12) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_031_009
_database_code_depnum_ccdc_archive 'CCDC 2151118'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;IBS KAIST
South Korea
;
_audit_update_record             
;
2022-02-09 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 N O6'
_chemical_formula_sum            'C18 H21 N O6'
_chemical_formula_weight         347.36

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.0300(3)
_cell_length_b                   20.5537(12)
_cell_length_c                   16.8829(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.379(2)
_cell_angle_gamma                90
_cell_volume                     1730.98(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.51

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.2627
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\^I1/4S 3.0 Microfocus'
_diffrn_measurement_device_type  'PHOTON II 14'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10870
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.139
_diffrn_reflns_theta_max         26.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.936
_reflns_number_total             3487
_reflns_number_gt                3186
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_max     0.856
_reflns_Friedel_fraction_full    0.891

_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 APEXIII'
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.1483P)²+0.7620P] 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_abs_structure_details 
;
 Flack x determined using 1228 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(8)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3487
_refine_ls_number_parameters     226
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0782
_refine_ls_wR_factor_ref         0.2152
_refine_ls_wR_factor_gt          0.2076
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.075
_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
C1 C 0.4030(9) 0.7123(2) 0.4041(3) 0.0279(9) Uani 1 1 d . . . . .
C2 C 0.5757(9) 0.7563(2) 0.3735(3) 0.0290(10) Uani 1 1 d . . . . .
C3 C 0.6313(12) 0.7547(2) 0.2953(3) 0.0365(11) Uani 1 1 d . . . . .
H3 H 0.750941 0.785334 0.277001 0.044 Uiso 1 1 calc R U . . .
C4 C 0.5109(13) 0.7081(2) 0.2448(3) 0.0396(12) Uani 1 1 d . . . . .
H4 H 0.547009 0.705990 0.190942 0.048 Uiso 1 1 calc R U . . .
C5 C 0.3350(12) 0.6639(2) 0.2729(3) 0.0389(12) Uani 1 1 d . . . . .
H5 H 0.250050 0.631919 0.237660 0.047 Uiso 1 1 calc R U . . .
C6 C 0.2812(9) 0.6656(2) 0.3521(3) 0.0299(10) Uani 1 1 d . . . . .
C7 C 0.0832(10) 0.6163(2) 0.3771(3) 0.0336(10) Uani 1 1 d . . . . .
H7A H -0.075685 0.639622 0.391589 0.040 Uiso 1 1 calc R U . . .
H7B H 0.022584 0.587783 0.330973 0.040 Uiso 1 1 calc R U . . .
O8 O 0.1930(6) 0.57622(15) 0.4437(2) 0.0305(7) Uani 1 1 d . . . . .
O9 O 0.4611(8) 0.52805(19) 0.3650(2) 0.0413(9) Uani 1 1 d . . . . .
C10 C 0.3843(8) 0.5323(2) 0.4279(3) 0.0276(9) Uani 1 1 d . . . . .
C11 C 0.4686(9) 0.4917(2) 0.5012(3) 0.0267(9) Uani 1 1 d . . . . .
H11A H 0.320318 0.461827 0.509696 0.032 Uiso 1 1 calc R U . . .
H11B H 0.500297 0.520716 0.548284 0.032 Uiso 1 1 calc R U . . .
C12 C 0.7195(9) 0.4520(2) 0.4957(3) 0.0289(9) Uani 1 1 d . . . . .
H12A H 0.863162 0.480793 0.480957 0.035 Uiso 1 1 calc R U . . .
H12B H 0.682084 0.418627 0.453444 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8150(11) 0.4183(2) 0.5770(3) 0.0349(10) Uani 1 1 d . . . . .
H13A H 0.663432 0.393949 0.594777 0.042 Uiso 1 1 calc R U . . .
H13B H 0.958381 0.386671 0.569715 0.042 Uiso 1 1 calc R U . . .
C14 C 0.9180(10) 0.4662(2) 0.6397(3) 0.0334(10) Uani 1 1 d . . . . .
H14 H 1.089000 0.484741 0.635982 0.040 Uiso 1 1 calc R U . . .
C15 C 0.7933(11) 0.4854(2) 0.6999(3) 0.0338(10) Uani 1 1 d . . . . .
H15 H 0.635248 0.462668 0.708709 0.041 Uiso 1 1 calc R U . . .
C16 C 0.8834(10) 0.5406(2) 0.7557(3) 0.0333(10) Uani 1 1 d . . . . .
H16A H 1.074693 0.550225 0.752809 0.040 Uiso 1 1 calc R U . . .
H16B H 0.864426 0.527889 0.811263 0.040 Uiso 1 1 calc R U . . .
C17 C 0.7142(10) 0.6012(2) 0.7327(3) 0.0318(10) Uani 1 1 d . . . . .
H17A H 0.748518 0.634022 0.775695 0.038 Uiso 1 1 calc R U . . .
H17B H 0.521793 0.589477 0.727439 0.038 Uiso 1 1 calc R U . . .
C18 C 0.7784(10) 0.6308(2) 0.6536(3) 0.0287(9) Uani 1 1 d . . . . .
H18A H 0.945869 0.656433 0.664188 0.034 Uiso 1 1 calc R U . . .
H18B H 0.810519 0.595109 0.616667 0.034 Uiso 1 1 calc R U . . .
C19 C 0.5614(9) 0.6738(2) 0.6136(3) 0.0276(9) Uani 1 1 d . . . . .
O20 O 0.3999(9) 0.7033(2) 0.6464(2) 0.0488(11) Uani 1 1 d . . . . .
O21 O 0.5610(7) 0.67513(17) 0.53482(19) 0.0332(8) Uani 1 1 d . . . . .
C22 C 0.3515(10) 0.7143(2) 0.4906(3) 0.0335(10) Uani 1 1 d . . . . .
H22A H 0.359729 0.759666 0.510659 0.040 Uiso 1 1 calc R U . . .
H22B H 0.172502 0.696213 0.496184 0.040 Uiso 1 1 calc R U . . .
N23 N 0.7072(10) 0.8085(2) 0.4235(3) 0.0406(11) Uani 1 1 d . . . . .
O24 O 0.7093(16) 0.8629(2) 0.3948(3) 0.083(2) Uani 1 1 d . . . . .
O25 O 0.8012(11) 0.7971(2) 0.4928(3) 0.0593(13) Uani 1 1 d . . . . .


_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
C1 C6 1.388(7) . ?
C1 C2 1.398(7) . ?
C1 C22 1.517(7) . ?
C2 C3 1.384(7) . ?
C2 N23 1.471(6) . ?
C3 C4 1.371(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.518(7) . ?
C7 O8 1.445(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O8 C10 1.370(5) . ?
O9 C10 1.179(6) . ?
C10 C11 1.509(6) . ?
C11 C12 1.516(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.558(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.489(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.322(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.506(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.531(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.539(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.496(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O20 1.204(6) . ?
C19 O21 1.331(5) . ?
O21 C22 1.454(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N23 O24 1.218(6) . ?
N23 O25 1.227(6) . ?

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
C6 C1 C2 117.3(4) . . ?
C6 C1 C22 120.8(4) . . ?
C2 C1 C22 121.9(4) . . ?
C3 C2 C1 123.3(4) . . ?
C3 C2 N23 115.7(4) . . ?
C1 C2 N23 121.0(4) . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 121.2(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.9(4) . . ?
C1 C6 C7 122.6(4) . . ?
C5 C6 C7 117.5(4) . . ?
O8 C7 C6 113.4(4) . . ?
O8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
O8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C10 O8 C7 115.5(4) . . ?
O9 C10 O8 123.0(4) . . ?
O9 C10 C11 127.5(4) . . ?
O8 C10 C11 109.6(4) . . ?
C10 C11 C12 113.3(4) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 110.5(4) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 111.8(4) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 126.0(5) . . ?
C15 C14 H14 117.0 . . ?
C13 C14 H14 117.0 . . ?
C14 C15 C16 124.8(5) . . ?
C14 C15 H15 117.6 . . ?
C16 C15 H15 117.6 . . ?
C15 C16 C17 110.0(4) . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 C18 111.7(4) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 113.7(4) . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
O20 C19 O21 122.3(4) . . ?
O20 C19 C18 125.9(4) . . ?
O21 C19 C18 111.7(4) . . ?
C19 O21 C22 115.6(4) . . ?
O21 C22 C1 106.0(4) . . ?
O21 C22 H22A 110.5 . . ?
C1 C22 H22A 110.5 . . ?
O21 C22 H22B 110.5 . . ?
C1 C22 H22B 110.5 . . ?
H22A C22 H22B 108.7 . . ?
O24 N23 O25 122.2(5) . . ?
O24 N23 C2 117.9(4) . . ?
O25 N23 C2 119.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.8(7) . . . . ?
C22 C1 C2 C3 178.5(4) . . . . ?
C6 C1 C2 N23 178.2(4) . . . . ?
C22 C1 C2 N23 -2.5(7) . . . . ?
C1 C2 C3 C4 0.4(8) . . . . ?
N23 C2 C3 C4 -178.6(5) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C3 C4 C5 C6 -0.7(8) . . . . ?
C2 C1 C6 C5 0.4(6) . . . . ?
C22 C1 C6 C5 -178.9(4) . . . . ?
C2 C1 C6 C7 -178.1(4) . . . . ?
C22 C1 C6 C7 2.5(6) . . . . ?
C4 C5 C6 C1 0.3(7) . . . . ?
C4 C5 C6 C7 179.0(5) . . . . ?
C1 C6 C7 O8 -58.3(6) . . . . ?
C5 C6 C7 O8 123.1(5) . . . . ?
C6 C7 O8 C10 -69.7(5) . . . . ?
C7 O8 C10 O9 1.8(6) . . . . ?
C7 O8 C10 C11 -176.9(3) . . . . ?
O9 C10 C11 C12 13.8(7) . . . . ?
O8 C10 C11 C12 -167.6(4) . . . . ?
C10 C11 C12 C13 172.9(4) . . . . ?
C11 C12 C13 C14 -68.9(5) . . . . ?
C12 C13 C14 C15 105.8(6) . . . . ?
C13 C14 C15 C16 -171.0(4) . . . . ?
C14 C15 C16 C17 101.6(6) . . . . ?
C15 C16 C17 C18 -70.5(5) . . . . ?
C16 C17 C18 C19 159.4(4) . . . . ?
C17 C18 C19 O20 26.3(7) . . . . ?
C17 C18 C19 O21 -152.3(4) . . . . ?
O20 C19 O21 C22 -0.4(7) . . . . ?
C18 C19 O21 C22 178.4(4) . . . . ?
C19 O21 C22 C1 176.1(4) . . . . ?
C6 C1 C22 O21 92.2(5) . . . . ?
C2 C1 C22 O21 -87.1(5) . . . . ?
C3 C2 N23 O24 43.9(8) . . . . ?
C1 C2 N23 O24 -135.1(6) . . . . ?
C3 C2 N23 O25 -138.8(6) . . . . ?
C1 C2 N23 O25 42.1(8) . . . . ?

_refine_diff_density_max         0.569
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_033_014
_database_code_depnum_ccdc_archive 'CCDC 2151120'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;IBS KAIST
South Korea
;
_audit_update_record             
;
2022-02-09 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 N O6'
_chemical_formula_sum            'C18 H21 N O6'
_chemical_formula_weight         347.36

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.150(4)
_cell_length_b                   9.733(3)
_cell_length_c                   10.702(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.541(7)
_cell_angle_gamma                90
_cell_volume                     1712.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9526
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      27.02

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.3322
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\^I1/4S 3.0 Microfocus'
_diffrn_measurement_device_type  'PHOTON II 14'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20258
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_av_R_equivalents  0.1536
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.478
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3188
_reflns_number_gt                2327
_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       'Bruker APEXIII'
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0475P)²+4.6038P] 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         3188
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1464
_refine_ls_R_factor_gt           0.1112
_refine_ls_wR_factor_ref         0.2349
_refine_ls_wR_factor_gt          0.2192
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_restrained_S_all      1.182
_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
C1 C 0.3831(3) 0.3716(5) 0.4416(4) 0.0291(10) Uani 1 1 d . . . . .
C2 C 0.3494(3) 0.4503(5) 0.3303(5) 0.0328(11) Uani 1 1 d . . . . .
H2 H 0.329220 0.404389 0.249136 0.039 Uiso 1 1 calc R U . . .
C3 C 0.3441(3) 0.5924(5) 0.3327(5) 0.0363(12) Uani 1 1 d . . . . .
H3 H 0.320304 0.640971 0.254098 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3731(3) 0.6647(5) 0.4486(5) 0.0320(11) Uani 1 1 d . . . . .
C5 C 0.4104(3) 0.5913(5) 0.5601(5) 0.0314(11) Uani 1 1 d . . . . .
H5 H 0.432403 0.638235 0.640259 0.038 Uiso 1 1 calc R U . . .
C6 C 0.4157(2) 0.4501(5) 0.5556(4) 0.0290(10) Uani 1 1 d . . . . .
C7 C 0.3817(3) 0.2171(5) 0.4328(5) 0.0354(11) Uani 1 1 d . . . . .
H7A H 0.437835 0.182336 0.446964 0.042 Uiso 1 1 calc R U . . .
H7B H 0.360061 0.178464 0.501761 0.042 Uiso 1 1 calc R U . . .
O8 O 0.33180(18) 0.1734(3) 0.3070(3) 0.0366(8) Uani 1 1 d . . . . .
O9 O 0.2230(2) 0.1767(4) 0.3837(3) 0.0433(9) Uani 1 1 d . . . . .
C10 C 0.2512(3) 0.1599(5) 0.2956(5) 0.0325(11) Uani 1 1 d . . . . .
C11 C 0.2051(3) 0.1161(5) 0.1583(5) 0.0373(12) Uani 1 1 d . . . . .
H11A H 0.212888 0.016121 0.149714 0.045 Uiso 1 1 calc R U . . .
H11B H 0.228969 0.163450 0.096062 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1140(3) 0.1462(6) 0.1203(5) 0.0430(13) Uani 1 1 d . . . . .
H12A H 0.086048 0.081521 0.050567 0.052 Uiso 1 1 calc R U . . .
H12B H 0.093803 0.128242 0.196677 0.052 Uiso 1 1 calc R U . . .
C13 C 0.0908(3) 0.2921(6) 0.0732(5) 0.0452(14) Uani 1 1 d . . . . .
H13A H 0.113696 0.311680 -0.000086 0.054 Uiso 1 1 calc R U . . .
H13B H 0.030864 0.297367 0.038940 0.054 Uiso 1 1 calc R U . . .
C14 C 0.1193(3) 0.4030(6) 0.1756(6) 0.0501(15) Uani 1 1 d . . . . .
H14 H 0.175660 0.402058 0.220796 0.060 Uiso 1 1 calc R U . . .
C15 C 0.0773(3) 0.4983(6) 0.2098(6) 0.0498(14) Uani 1 1 d . . . . .
H15 H 0.021149 0.504214 0.163944 0.060 Uiso 1 1 calc R U . . .
C16 C 0.1104(4) 0.6000(5) 0.3157(5) 0.0473(14) Uani 1 1 d . . . . .
H16A H 0.167334 0.575110 0.361252 0.057 Uiso 1 1 calc R U . . .
H16B H 0.078685 0.593719 0.379690 0.057 Uiso 1 1 calc R U . . .
C17 C 0.1083(3) 0.7470(5) 0.2689(5) 0.0386(12) Uani 1 1 d . . . . .
H17A H 0.051682 0.771254 0.220421 0.046 Uiso 1 1 calc R U . . .
H17B H 0.141979 0.754674 0.207938 0.046 Uiso 1 1 calc R U . . .
C18 C 0.1395(3) 0.8495(5) 0.3810(5) 0.0377(12) Uani 1 1 d . . . . .
H18A H 0.136364 0.943733 0.345213 0.045 Uiso 1 1 calc R U . . .
H18B H 0.104328 0.845303 0.439950 0.045 Uiso 1 1 calc R U . . .
C19 C 0.2255(3) 0.8190(5) 0.4570(5) 0.0348(11) Uani 1 1 d . . . . .
O20 O 0.2472(2) 0.7661(4) 0.5625(3) 0.0466(10) Uani 1 1 d . . . . .
O21 O 0.27852(19) 0.8556(3) 0.3897(3) 0.0376(8) Uani 1 1 d . . . . .
C22 C 0.3633(3) 0.8173(5) 0.4499(5) 0.0365(12) Uani 1 1 d . . . . .
H22A H 0.380862 0.851048 0.540863 0.044 Uiso 1 1 calc R U . . .
H22B H 0.398224 0.860846 0.401676 0.044 Uiso 1 1 calc R U . . .
N23 N 0.4605(2) 0.3813(4) 0.6787(4) 0.0354(10) Uani 1 1 d . . . . .
O24 O 0.4851(2) 0.4539(4) 0.7770(3) 0.0444(9) Uani 1 1 d . . . . .
O25 O 0.4723(2) 0.2588(4) 0.6770(3) 0.0475(10) Uani 1 1 d . . . . .


_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
C1 C2 1.395(6) . ?
C1 C6 1.413(7) . ?
C1 C7 1.506(7) . ?
C2 C3 1.387(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(6) . ?
C4 C22 1.495(7) . ?
C5 C6 1.379(7) . ?
C5 H5 0.9500 . ?
C6 N23 1.482(6) . ?
C7 O8 1.440(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O8 C10 1.359(5) . ?
O9 C10 1.188(6) . ?
C10 C11 1.517(7) . ?
C11 C12 1.526(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.521(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.289(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.489(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.513(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.535(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.497(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O20 1.200(6) . ?
C19 O21 1.359(6) . ?
O21 C22 1.461(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N23 O25 1.211(5) . ?
N23 O24 1.237(5) . ?

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
C2 C1 C6 114.0(4) . . ?
C2 C1 C7 120.0(4) . . ?
C6 C1 C7 126.1(4) . . ?
C3 C2 C1 123.0(5) . . ?
C3 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C2 C3 C4 120.9(5) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.0(4) . . ?
C5 C4 C22 122.1(4) . . ?
C3 C4 C22 119.9(4) . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 123.7(4) . . ?
C5 C6 N23 116.2(4) . . ?
C1 C6 N23 120.1(4) . . ?
O8 C7 C1 110.3(4) . . ?
O8 C7 H7A 109.6 . . ?
C1 C7 H7A 109.6 . . ?
O8 C7 H7B 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C10 O8 C7 115.6(4) . . ?
O9 C10 O8 123.3(4) . . ?
O9 C10 C11 126.1(4) . . ?
O8 C10 C11 110.5(4) . . ?
C10 C11 C12 114.6(4) . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 114.8(4) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 115.1(4) . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 128.8(5) . . ?
C15 C14 H14 115.6 . . ?
C13 C14 H14 115.6 . . ?
C14 C15 C16 124.8(5) . . ?
C14 C15 H15 117.6 . . ?
C16 C15 H15 117.6 . . ?
C15 C16 C17 114.1(4) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C18 112.7(4) . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C17 111.5(4) . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
O20 C19 O21 122.5(4) . . ?
O20 C19 C18 126.1(5) . . ?
O21 C19 C18 111.4(4) . . ?
C19 O21 C22 115.6(4) . . ?
O21 C22 C4 110.5(4) . . ?
O21 C22 H22A 109.6 . . ?
C4 C22 H22A 109.6 . . ?
O21 C22 H22B 109.6 . . ?
C4 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
O25 N23 O24 123.9(4) . . ?
O25 N23 C6 118.5(4) . . ?
O24 N23 C6 117.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -3.7(6) . . . . ?
C7 C1 C2 C3 176.0(4) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C3 C4 C5 2.7(7) . . . . ?
C2 C3 C4 C22 -177.3(4) . . . . ?
C3 C4 C5 C6 -2.1(6) . . . . ?
C22 C4 C5 C6 177.9(4) . . . . ?
C4 C5 C6 C1 -1.5(7) . . . . ?
C4 C5 C6 N23 177.0(4) . . . . ?
C2 C1 C6 C5 4.3(6) . . . . ?
C7 C1 C6 C5 -175.3(4) . . . . ?
C2 C1 C6 N23 -174.2(4) . . . . ?
C7 C1 C6 N23 6.2(6) . . . . ?
C2 C1 C7 O8 -9.3(6) . . . . ?
C6 C1 C7 O8 170.3(4) . . . . ?
C1 C7 O8 C10 -86.6(5) . . . . ?
C7 O8 C10 O9 -3.1(7) . . . . ?
C7 O8 C10 C11 179.0(4) . . . . ?
O9 C10 C11 C12 22.8(7) . . . . ?
O8 C10 C11 C12 -159.4(4) . . . . ?
C10 C11 C12 C13 83.0(6) . . . . ?
C11 C12 C13 C14 -66.5(6) . . . . ?
C12 C13 C14 C15 -127.2(7) . . . . ?
C13 C14 C15 C16 177.5(5) . . . . ?
C14 C15 C16 C17 115.0(7) . . . . ?
C15 C16 C17 C18 177.7(4) . . . . ?
C16 C17 C18 C19 59.5(6) . . . . ?
C17 C18 C19 O20 -104.4(6) . . . . ?
C17 C18 C19 O21 73.9(5) . . . . ?
O20 C19 O21 C22 4.3(7) . . . . ?
C18 C19 O21 C22 -174.0(4) . . . . ?
C19 O21 C22 C4 68.3(5) . . . . ?
C5 C4 C22 O21 -127.7(4) . . . . ?
C3 C4 C22 O21 52.3(6) . . . . ?
C5 C6 N23 O25 -174.3(4) . . . . ?
C1 C6 N23 O25 4.4(6) . . . . ?
C5 C6 N23 O24 4.1(6) . . . . ?
C1 C6 N23 O24 -177.3(4) . . . . ?

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_032_014
_database_code_depnum_ccdc_archive 'CCDC 2151117'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;IBS KAIST
South Korea
;
_audit_update_record             
;
2022-02-09 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N O6'
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.30

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1387(4)
_cell_length_b                   24.2934(10)
_cell_length_c                   8.5069(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.4138(13)
_cell_angle_gamma                90
_cell_volume                     1493.08(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6131
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34884
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.825
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3658
_reflns_number_gt                3286
_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       'Bruker APEXIII'
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0542P)²+0.6173P] 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         3658
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
C1 C 0.35475(17) 0.39629(5) 0.49281(17) 0.0270(2) Uani 1 1 d . . . . .
C2 C 0.47791(17) 0.42192(5) 0.65126(16) 0.0262(2) Uani 1 1 d . . . . .
C3 C 0.43535(19) 0.47635(5) 0.67545(17) 0.0298(3) Uani 1 1 d . . . . .
C4 C 0.2805(2) 0.50405(5) 0.5534(2) 0.0369(3) Uani 1 1 d . . . . .
H4 H 0.256877 0.540818 0.575294 0.044 Uiso 1 1 calc R U . . .
C5 C 0.1611(2) 0.47765(6) 0.3998(2) 0.0400(3) Uani 1 1 d . . . . .
H5 H 0.053843 0.496005 0.314862 0.048 Uiso 1 1 calc R U . . .
C6 C 0.19845(19) 0.42418(6) 0.36995(18) 0.0341(3) Uani 1 1 d . . . . .
H6 H 0.115948 0.406100 0.263634 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3877(2) 0.33951(5) 0.44205(19) 0.0322(3) Uani 1 1 d . . . . .
H7A H 0.453112 0.316213 0.548531 0.039 Uiso 1 1 calc R U . . .
H7B H 0.268972 0.321624 0.361997 0.039 Uiso 1 1 calc R U . . .
O8 O 0.50109(13) 0.34768(3) 0.35255(12) 0.0301(2) Uani 1 1 d . . . . .
O9 O 0.49099(15) 0.25692(4) 0.30395(14) 0.0362(2) Uani 1 1 d . . . . .
C10 C 0.54065(16) 0.30217(5) 0.28712(15) 0.0247(2) Uani 1 1 d . . . . .
C11 C 0.65499(18) 0.31475(5) 0.19472(16) 0.0284(3) Uani 1 1 d . . . . .
H11A H 0.656703 0.355014 0.177548 0.034 Uiso 1 1 calc R U . . .
H11B H 0.598372 0.297105 0.076548 0.034 Uiso 1 1 calc R U . . .
C12 C 0.85286(19) 0.29394(6) 0.30186(18) 0.0337(3) Uani 1 1 d . . . . .
H12A H 0.850320 0.253922 0.322653 0.040 Uiso 1 1 calc R U . . .
H12B H 0.921666 0.299640 0.232849 0.040 Uiso 1 1 calc R U . . .
C13 C 0.95312(18) 0.32320(5) 0.47855(19) 0.0331(3) Uani 1 1 d . . . . .
H13 H 0.923282 0.360731 0.483819 0.040 Uiso 1 1 calc R U . . .
C14 C 1.07781(18) 0.30045(5) 0.62435(18) 0.0330(3) Uani 1 1 d . . . . .
H14 H 1.099633 0.262223 0.619357 0.040 Uiso 1 1 calc R U . . .
C15 C 1.18927(18) 0.32854(6) 0.79780(18) 0.0344(3) Uani 1 1 d . . . . .
H15A H 1.314625 0.335509 0.810435 0.041 Uiso 1 1 calc R U . . .
H15B H 1.202997 0.302886 0.893525 0.041 Uiso 1 1 calc R U . . .
C16 C 1.11250(17) 0.38282(5) 0.82645(19) 0.0327(3) Uani 1 1 d . . . . .
H16A H 1.211662 0.402942 0.926260 0.039 Uiso 1 1 calc R U . . .
H16B H 1.071172 0.405888 0.718957 0.039 Uiso 1 1 calc R U . . .
C17 C 0.95261(17) 0.37337(5) 0.86588(16) 0.0282(3) Uani 1 1 d . . . . .
O18 O 0.96218(15) 0.34658(5) 0.98886(14) 0.0428(3) Uani 1 1 d . . . . .
O19 O 0.79566(12) 0.39799(4) 0.75015(12) 0.0298(2) Uani 1 1 d . . . . .
C20 C 0.64037(18) 0.39086(5) 0.78877(18) 0.0311(3) Uani 1 1 d . . . . .
H20A H 0.672519 0.405240 0.908335 0.037 Uiso 1 1 calc R U . . .
H20B H 0.609514 0.351312 0.785342 0.037 Uiso 1 1 calc R U . . .
N21 N 0.55794(19) 0.50826(5) 0.83422(17) 0.0377(3) Uani 1 1 d . . . . .
O22 O 0.48633(19) 0.54517(4) 0.88106(16) 0.0496(3) Uani 1 1 d . . . . .
O23 O 0.72318(16) 0.49758(5) 0.91000(16) 0.0510(3) Uani 1 1 d . . . . .


_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
C1 C6 1.3946(19) . ?
C1 C2 1.4018(18) . ?
C1 C7 1.5060(17) . ?
C2 C3 1.4057(17) . ?
C2 C20 1.5040(18) . ?
C3 C4 1.384(2) . ?
C3 N21 1.4765(18) . ?
C4 C5 1.376(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O8 1.4554(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O8 C10 1.3418(14) . ?
O9 C10 1.2024(15) . ?
C10 C11 1.5003(17) . ?
C11 C12 1.5259(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5169(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.3094(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.4944(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.5262(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5035(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O18 1.2038(16) . ?
C17 O19 1.3418(15) . ?
O19 C20 1.4552(14) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N21 O23 1.2219(18) . ?
N21 O22 1.2314(16) . ?

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
C6 C1 C2 120.43(11) . . ?
C6 C1 C7 116.83(12) . . ?
C2 C1 C7 122.66(12) . . ?
C1 C2 C3 116.31(11) . . ?
C1 C2 C20 120.55(11) . . ?
C3 C2 C20 123.08(12) . . ?
C4 C3 C2 123.25(12) . . ?
C4 C3 N21 115.44(12) . . ?
C2 C3 N21 121.30(12) . . ?
C5 C4 C3 119.13(12) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 119.55(13) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 121.32(13) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O8 C7 C1 105.34(9) . . ?
O8 C7 H7A 110.7 . . ?
C1 C7 H7A 110.7 . . ?
O8 C7 H7B 110.7 . . ?
C1 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C10 O8 C7 115.83(9) . . ?
O9 C10 O8 123.09(11) . . ?
O9 C10 C11 124.90(11) . . ?
O8 C10 C11 112.01(10) . . ?
C10 C11 C12 110.99(10) . . ?
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 112.02(11) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 124.72(12) . . ?
C14 C13 H13 117.6 . . ?
C12 C13 H13 117.6 . . ?
C13 C14 C15 126.58(12) . . ?
C13 C14 H14 116.7 . . ?
C15 C14 H14 116.7 . . ?
C14 C15 C16 116.44(11) . . ?
C14 C15 H15A 108.2 . . ?
C16 C15 H15A 108.2 . . ?
C14 C15 H15B 108.2 . . ?
C16 C15 H15B 108.2 . . ?
H15A C15 H15B 107.3 . . ?
C17 C16 C15 111.33(11) . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O18 C17 O19 122.51(12) . . ?
O18 C17 C16 124.06(12) . . ?
O19 C17 C16 113.43(11) . . ?
C17 O19 C20 114.44(10) . . ?
O19 C20 C2 107.98(9) . . ?
O19 C20 H20A 110.1 . . ?
C2 C20 H20A 110.1 . . ?
O19 C20 H20B 110.1 . . ?
C2 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
O23 N21 O22 123.63(13) . . ?
O23 N21 C3 119.15(11) . . ?
O22 N21 C3 117.21(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.89(17) . . . . ?
C7 C1 C2 C3 175.91(10) . . . . ?
C6 C1 C2 C20 176.35(11) . . . . ?
C7 C1 C2 C20 -6.84(17) . . . . ?
C1 C2 C3 C4 0.78(17) . . . . ?
C20 C2 C3 C4 -176.40(11) . . . . ?
C1 C2 C3 N21 -177.92(10) . . . . ?
C20 C2 C3 N21 4.91(17) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
N21 C3 C4 C5 178.59(12) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C2 C1 C6 C5 0.45(19) . . . . ?
C7 C1 C6 C5 -176.53(12) . . . . ?
C6 C1 C7 O8 90.11(13) . . . . ?
C2 C1 C7 O8 -86.80(14) . . . . ?
C1 C7 O8 C10 -176.86(10) . . . . ?
C7 O8 C10 O9 -1.89(17) . . . . ?
C7 O8 C10 C11 178.99(10) . . . . ?
O9 C10 C11 C12 -70.24(16) . . . . ?
O8 C10 C11 C12 108.86(12) . . . . ?
C10 C11 C12 C13 -64.13(14) . . . . ?
C11 C12 C13 C14 146.67(13) . . . . ?
C12 C13 C14 C15 175.48(12) . . . . ?
C13 C14 C15 C16 20.3(2) . . . . ?
C14 C15 C16 C17 75.73(15) . . . . ?
C15 C16 C17 O18 58.82(17) . . . . ?
C15 C16 C17 O19 -121.35(12) . . . . ?
O18 C17 O19 C20 1.66(17) . . . . ?
C16 C17 O19 C20 -178.17(10) . . . . ?
C17 O19 C20 C2 178.43(10) . . . . ?
C1 C2 C20 O19 89.29(13) . . . . ?
C3 C2 C20 O19 -93.66(13) . . . . ?
C4 C3 N21 O23 -151.17(13) . . . . ?
C2 C3 N21 O23 27.62(17) . . . . ?
C4 C3 N21 O22 27.73(16) . . . . ?
C2 C3 N21 O22 -153.48(12) . . . . ?

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_027_014
_database_code_depnum_ccdc_archive 'CCDC 2151119'
loop_
_audit_author_name
_audit_author_address
'Dongwook Kim'
;IBS KAIST
South Korea
;
_audit_update_record             
;
2022-02-09 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N O6'
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.30

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.8712(4)
_cell_length_b                   16.4752(7)
_cell_length_c                   11.7570(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.5968(14)
_cell_angle_gamma                90
_cell_volume                     1524.05(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8543
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      27.47

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6508
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\^I1/4S 3.0 Microfocus'
_diffrn_measurement_device_type  'PHOTON II 14'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20523
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.869
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3447
_reflns_number_gt                2852
_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       'Bruker APEXIII'
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_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)+(0.0317P)²+0.4916P] 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         3447
_refine_ls_number_parameters     245
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.024
_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
C1 C 0.41523(16) 0.55267(7) 0.64524(12) 0.0309(3) Uani 1 1 d . . . . .
H1A H 0.381964 0.543439 0.724794 0.037 Uiso 1 1 calc R U . . .
H1B H 0.339511 0.519946 0.594632 0.037 Uiso 1 1 calc R U . . .
O2 O 0.59135(11) 0.52796(5) 0.63145(7) 0.0299(2) Uani 1 1 d . . . . .
O3 O 0.66097(12) 0.57846(6) 0.80421(8) 0.0357(2) Uani 1 1 d . . . . .
C4 C 0.70340(16) 0.54994(7) 0.71498(10) 0.0267(3) Uani 1 1 d . . . . .
C5 C 0.88193(17) 0.53591(8) 0.67928(11) 0.0323(3) Uani 1 1 d D . . . .
H5A H 0.892042 0.480420 0.647863 0.039 Uiso 1 1 calc R U . A 1
H5B H 0.960157 0.540279 0.746408 0.039 Uiso 1 1 calc R U . A 1
C6 C 0.9330(4) 0.59829(10) 0.58883(17) 0.0307(4) Uani 0.923(4) 1 d . U P B 1
H6A H 1.041152 0.581064 0.555230 0.037 Uiso 0.923(4) 1 calc R U P B 1
H6B H 0.844792 0.599519 0.527164 0.037 Uiso 0.923(4) 1 calc R U P B 1
C7 C 0.9542(2) 0.68215(9) 0.63751(12) 0.0291(4) Uani 0.923(4) 1 d . U P B 1
H7 H 1.039147 0.689779 0.695479 0.035 Uiso 0.923(4) 1 calc R U P B 1
C8 C 0.8630(3) 0.74619(10) 0.60552(13) 0.0303(4) Uani 0.923(4) 1 d . U P B 1
H8 H 0.773749 0.738115 0.550658 0.036 Uiso 0.923(4) 1 calc R U P B 1
C9 C 0.8914(4) 0.83122(15) 0.6503(2) 0.0348(5) Uani 0.923(4) 1 d . U P B 1
H9A H 1.004427 0.833879 0.689265 0.042 Uiso 0.923(4) 1 calc R U P B 1
H9B H 0.804780 0.843266 0.707413 0.042 Uiso 0.923(4) 1 calc R U P B 1
C6B C 0.924(5) 0.6128(10) 0.608(2) 0.033(3) Uani 0.077(4) 1 d D U P B 2
H6BA H 1.049079 0.614036 0.604442 0.039 Uiso 0.077(4) 1 calc R U P B 2
H6BB H 0.880883 0.600887 0.529980 0.039 Uiso 0.077(4) 1 calc R U P B 2
C7B C 0.870(3) 0.7012(11) 0.6317(16) 0.030(2) Uani 0.077(4) 1 d D U P B 2
H7B H 0.770306 0.707727 0.674275 0.036 Uiso 0.077(4) 1 calc R U P B 2
C8B C 0.938(3) 0.7618(13) 0.6034(17) 0.034(2) Uani 0.077(4) 1 d D U P B 2
H8B H 1.027884 0.762946 0.551500 0.040 Uiso 0.077(4) 1 calc R U P B 2
C9B C 0.865(6) 0.8387(13) 0.6586(19) 0.031(3) Uani 0.077(4) 1 d D U P B 2
H9BA H 0.934742 0.856547 0.725477 0.037 Uiso 0.077(4) 1 calc R U P B 2
H9BB H 0.745598 0.831559 0.680357 0.037 Uiso 0.077(4) 1 calc R U P B 2
C10 C 0.88198(18) 0.89665(8) 0.55649(12) 0.0367(3) Uani 1 1 d D . . . .
H10A H 0.904726 0.950573 0.590803 0.044 Uiso 1 1 calc R U . B 1
H10B H 0.970736 0.885926 0.500386 0.044 Uiso 1 1 calc R U . B 1
C11 C 0.71098(18) 0.89756(7) 0.49688(11) 0.0321(3) Uani 1 1 d . . . . .
O12 O 0.68344(15) 0.88174(8) 0.39850(9) 0.0533(3) Uani 1 1 d . . . . .
O13 O 0.58662(11) 0.91684(5) 0.56921(7) 0.0292(2) Uani 1 1 d . . . . .
C14 C 0.41387(17) 0.89612(8) 0.53173(11) 0.0318(3) Uani 1 1 d . . . . .
H14A H 0.399046 0.904491 0.448660 0.038 Uiso 1 1 calc R U . . .
H14B H 0.330635 0.930494 0.571016 0.038 Uiso 1 1 calc R U . . .
C15 C 0.38826(15) 0.80802(7) 0.56129(10) 0.0253(2) Uani 1 1 d . . . . .
C16 C 0.37481(17) 0.74905(8) 0.47702(11) 0.0314(3) Uani 1 1 d . . . . .
H16 H 0.362867 0.765168 0.399629 0.038 Uiso 1 1 calc R U . . .
C17 C 0.37853(16) 0.66690(8) 0.50393(11) 0.0301(3) Uani 1 1 d . . . . .
H17 H 0.368063 0.627768 0.444797 0.036 Uiso 1 1 calc R U . . .
C18 C 0.39730(14) 0.64131(7) 0.61593(10) 0.0252(3) Uani 1 1 d . . . . .
C19 C 0.40774(14) 0.69914(7) 0.70212(10) 0.0236(2) Uani 1 1 d . . . . .
H19 H 0.418971 0.683036 0.779554 0.028 Uiso 1 1 calc R U . . .
C20 C 0.40150(14) 0.78028(7) 0.67318(10) 0.0222(2) Uani 1 1 d . . . . .
N21 N 0.41417(13) 0.83802(6) 0.76867(9) 0.0269(2) Uani 1 1 d . . . . .
O22 O 0.31178(13) 0.89409(6) 0.77136(9) 0.0408(3) Uani 1 1 d . . . . .
O23 O 0.52548(13) 0.82633(6) 0.84143(8) 0.0392(2) Uani 1 1 d . . . . .


_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
C1 O2 1.4581(15) . ?
C1 C18 1.5062(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C4 1.3510(15) . ?
O3 C4 1.2052(15) . ?
C4 C5 1.4958(18) . ?
C5 C6 1.540(2) . ?
C5 C6B 1.558(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.503(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.324(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.511(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.543(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C6B C7B 1.542(10) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C8B 1.18(3) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.539(10) . ?
C8B H8B 0.9500 . ?
C9B C10 1.542(10) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10 C11 1.500(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O12 1.1995(17) . ?
C11 O13 1.3522(15) . ?
O13 C14 1.4582(16) . ?
C14 C15 1.5074(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.3896(17) . ?
C15 C20 1.3938(16) . ?
C16 C17 1.3901(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.3867(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3917(16) . ?
C19 C20 1.3799(16) . ?
C19 H19 0.9500 . ?
C20 N21 1.4728(14) . ?
N21 O23 1.2226(14) . ?
N21 O22 1.2269(13) . ?

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
O2 C1 C18 109.18(9) . . ?
O2 C1 H1A 109.8 . . ?
C18 C1 H1A 109.8 . . ?
O2 C1 H1B 109.8 . . ?
C18 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
C4 O2 C1 116.60(9) . . ?
O3 C4 O2 123.10(12) . . ?
O3 C4 C5 126.15(12) . . ?
O2 C4 C5 110.73(10) . . ?
C4 C5 C6 110.85(14) . . ?
C4 C5 C6B 103.8(13) . . ?
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 112.26(14) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 124.81(19) . . ?
C8 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
C7 C8 C9 124.5(2) . . ?
C7 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
C8 C9 C10 113.2(2) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C7B C6B C5 127.5(17) . . ?
C7B C6B H6BA 105.4 . . ?
C5 C6B H6BA 105.4 . . ?
C7B C6B H6BB 105.4 . . ?
C5 C6B H6BB 105.4 . . ?
H6BA C6B H6BB 106.0 . . ?
C8B C7B C6B 128(2) . . ?
C8B C7B H7B 115.8 . . ?
C6B C7B H7B 115.8 . . ?
C7B C8B C9B 114(3) . . ?
C7B C8B H8B 123.1 . . ?
C9B C8B H8B 123.1 . . ?
C8B C9B C10 98.1(13) . . ?
C8B C9B H9BA 112.1 . . ?
C10 C9B H9BA 112.1 . . ?
C8B C9B H9BB 112.1 . . ?
C10 C9B H9BB 112.1 . . ?
H9BA C9B H9BB 109.8 . . ?
C11 C10 C9B 106.0(19) . . ?
C11 C10 C9 111.45(17) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
O12 C11 O13 122.88(13) . . ?
O12 C11 C10 125.73(13) . . ?
O13 C11 C10 111.37(11) . . ?
C11 O13 C14 116.12(10) . . ?
O13 C14 C15 106.57(10) . . ?
O13 C14 H14A 110.4 . . ?
C15 C14 H14A 110.4 . . ?
O13 C14 H14B 110.4 . . ?
C15 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
C16 C15 C20 116.48(11) . . ?
C16 C15 C14 121.12(11) . . ?
C20 C15 C14 121.77(11) . . ?
C15 C16 C17 121.18(12) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 120.87(11) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.07(11) . . ?
C17 C18 C1 121.26(11) . . ?
C19 C18 C1 119.60(11) . . ?
C20 C19 C18 118.86(11) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C15 123.48(10) . . ?
C19 C20 N21 115.89(10) . . ?
C15 C20 N21 120.62(10) . . ?
O23 N21 O22 123.98(10) . . ?
O23 N21 C20 117.62(10) . . ?
O22 N21 C20 118.39(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 C1 O2 C4 77.30(13) . . . . ?
C1 O2 C4 O3 10.05(16) . . . . ?
C1 O2 C4 C5 -168.47(10) . . . . ?
O3 C4 C5 C6 -106.54(16) . . . . ?
O2 C4 C5 C6 71.92(15) . . . . ?
O3 C4 C5 C6B -95.6(14) . . . . ?
O2 C4 C5 C6B 82.8(14) . . . . ?
C4 C5 C6 C7 70.5(2) . . . . ?
C5 C6 C7 C8 -118.4(2) . . . . ?
C6 C7 C8 C9 -176.53(18) . . . . ?
C7 C8 C9 C10 136.7(2) . . . . ?
C4 C5 C6B C7B 38(4) . . . . ?
C5 C6B C7B C8B 155(3) . . . . ?
C6B C7B C8B C9B -170(3) . . . . ?
C7B C8B C9B C10 -144(2) . . . . ?
C8B C9B C10 C11 97(2) . . . . ?
C8 C9 C10 C11 60.6(2) . . . . ?
C9B C10 C11 O12 -124.2(9) . . . . ?
C9 C10 C11 O12 -115.74(17) . . . . ?
C9B C10 C11 O13 54.3(9) . . . . ?
C9 C10 C11 O13 62.70(15) . . . . ?
O12 C11 O13 C14 16.44(17) . . . . ?
C10 C11 O13 C14 -162.04(10) . . . . ?
C11 O13 C14 C15 83.12(12) . . . . ?
O13 C14 C15 C16 -110.22(13) . . . . ?
O13 C14 C15 C20 60.34(14) . . . . ?
C20 C15 C16 C17 -1.44(18) . . . . ?
C14 C15 C16 C17 169.59(12) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C16 C17 C18 C19 1.78(18) . . . . ?
C16 C17 C18 C1 -175.15(11) . . . . ?
O2 C1 C18 C17 81.83(14) . . . . ?
O2 C1 C18 C19 -95.08(13) . . . . ?
C17 C18 C19 C20 -0.92(17) . . . . ?
C1 C18 C19 C20 176.07(10) . . . . ?
C18 C19 C20 C15 -1.20(17) . . . . ?
C18 C19 C20 N21 -179.68(10) . . . . ?
C16 C15 C20 C19 2.36(17) . . . . ?
C14 C15 C20 C19 -168.62(11) . . . . ?
C16 C15 C20 N21 -179.23(11) . . . . ?
C14 C15 C20 N21 9.80(17) . . . . ?
C19 C20 N21 O23 46.63(15) . . . . ?
C15 C20 N21 O23 -131.90(12) . . . . ?
C19 C20 N21 O22 -132.46(11) . . . . ?
C15 C20 N21 O22 49.01(15) . . . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.036

