# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_LY20200514
_database_code_depnum_ccdc_archive 'CCDC 2072987'
loop_
_audit_author_name
_audit_author_address
'Yao liu'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2021-03-25 deposited with the CCDC.	2024-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C15H18N2O5
_chemical_formula_sum            'C15 H18 N2 O5'
_chemical_formula_weight         306.31

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                   7.7482(6)
_cell_length_b                   17.8486(11)
_cell_length_c                   10.7825(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.153(7)
_cell_angle_gamma                90
_cell_volume                     1488.90(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7516
_cell_measurement_theta_min      3.8730
_cell_measurement_theta_max      28.4470

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.6342
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16777
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.326
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2772
_reflns_number_gt                2259
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1032P)²+4.5096P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2772
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.1083
_refine_ls_wR_factor_ref         0.2799
_refine_ls_wR_factor_gt          0.2724
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.3926(13) 0.0543(4) 1.3616(6) 0.110(3) Uani 1 1 d . . . . .
H1A H 0.4471 0.0965 1.3249 0.165 Uiso 1 1 calc R U . . .
H1B H 0.4435 0.0460 1.4437 0.165 Uiso 1 1 calc R U . . .
H1C H 0.2713 0.0640 1.3663 0.165 Uiso 1 1 calc R U . . .
C2 C 0.4172(8) -0.0135(3) 1.2842(4) 0.0563(14) Uani 1 1 d . . . . .
H2A H 0.5393 -0.0227 1.2757 0.068 Uiso 1 1 calc R U . . .
H2B H 0.3674 -0.0571 1.3225 0.068 Uiso 1 1 calc R U . . .
C3 C 0.3250(6) -0.0564(2) 1.0841(4) 0.0418(11) Uani 1 1 d . . . . .
C4 C 0.2306(6) -0.0376(2) 0.9635(4) 0.0386(10) Uani 1 1 d . . . . .
C5 C 0.1455(6) -0.1625(3) 0.9244(4) 0.0411(10) Uani 1 1 d . . . . .
H5 H 0.1707 -0.1723 1.0082 0.049 Uiso 1 1 calc R U . . .
C6 C 0.0466(9) -0.2080(3) 0.7208(5) 0.0652(16) Uani 1 1 d . . . . .
H6A H -0.0384 -0.1692 0.7082 0.098 Uiso 1 1 calc R U . . .
H6B H 0.0025 -0.2539 0.6852 0.098 Uiso 1 1 calc R U . . .
H6C H 0.1501 -0.1940 0.6816 0.098 Uiso 1 1 calc R U . . .
C7 C 0.0641(8) -0.2926(3) 0.9028(5) 0.0577(14) Uani 1 1 d . . . . .
H7A H 0.1095 -0.2936 0.9875 0.087 Uiso 1 1 calc R U . . .
H7B H 0.1255 -0.3281 0.8550 0.087 Uiso 1 1 calc R U . . .
H7C H -0.0564 -0.3054 0.8997 0.087 Uiso 1 1 calc R U . . .
C8 C 0.2133(6) 0.0351(2) 0.9328(4) 0.0394(10) Uani 1 1 d . . . . .
H8 H 0.2646 0.0669 0.9924 0.047 Uiso 1 1 calc R U . . .
C9 C 0.1325(6) 0.0755(2) 0.8273(4) 0.0374(10) Uani 1 1 d . . . . .
C10 C 0.0783(6) 0.0456(3) 0.7103(4) 0.0452(11) Uani 1 1 d . . . . .
C11 C -0.0012(7) 0.0909(3) 0.6169(4) 0.0500(12) Uani 1 1 d . . . . .
H11 H -0.0367 0.0713 0.5398 0.060 Uiso 1 1 calc R U . . .
C12 C -0.0242(6) 0.1647(3) 0.6440(4) 0.0447(11) Uani 1 1 d . . . . .
C13 C 0.0331(6) 0.1957(3) 0.7558(4) 0.0417(10) Uani 1 1 d . . . . .
C14 C 0.1114(6) 0.1532(2) 0.8462(4) 0.0407(10) Uani 1 1 d . . . . .
H14 H 0.1513 0.1751 0.9206 0.049 Uiso 1 1 calc R U . . .
C15 C -0.0830(7) 0.2871(3) 0.6390(5) 0.0564(14) Uani 1 1 d . . . . .
H15A H -0.0146 0.3232 0.5958 0.068 Uiso 1 1 calc R U . . .
H15B H -0.1968 0.3083 0.6482 0.068 Uiso 1 1 calc R U . . .
N1 N 0.1711(5) -0.0956(2) 0.8838(3) 0.0417(9) Uani 1 1 d . . . . .
N2 N 0.0849(6) -0.2183(2) 0.8522(4) 0.0485(10) Uani 1 1 d . . . . .
O1 O 0.3312(5) 0.00060(18) 1.1638(3) 0.0530(10) Uani 1 1 d . . . . .
O2 O 0.3890(5) -0.11684(18) 1.1090(3) 0.0597(10) Uani 1 1 d . . . . .
O3 O 0.1057(6) -0.0256(2) 0.6778(3) 0.0708(13) Uani 1 1 d . . . . .
H3 H 0.1261 -0.0508 0.7404 0.106 Uiso 1 1 calc R U . . .
O4 O -0.0032(6) 0.2716(2) 0.7570(3) 0.0710(12) Uani 1 1 d . . . . .
O5 O -0.0976(6) 0.2191(2) 0.5687(3) 0.0688(12) 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 1.488(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.449(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O2 1.211(5) . ?
C3 O1 1.330(5) . ?
C3 C4 1.495(6) . ?
C4 C8 1.343(6) . ?
C4 N1 1.407(5) . ?
C5 N1 1.292(6) . ?
C5 N2 1.333(6) . ?
C5 H5 0.9300 . ?
C6 N2 1.444(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 N2 1.446(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.459(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.412(6) . ?
C9 C14 1.413(6) . ?
C10 O3 1.338(6) . ?
C10 C11 1.407(6) . ?
C11 C12 1.362(7) . ?
C11 H11 0.9300 . ?
C12 O5 1.369(6) . ?
C12 C13 1.377(6) . ?
C13 C14 1.352(6) . ?
C13 O4 1.383(5) . ?
C14 H14 0.9300 . ?
C15 O4 1.411(6) . ?
C15 O5 1.432(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O3 H3 0.8200 . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 107.1(4) . . ?
O1 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
O1 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 O1 122.6(4) . . ?
O2 C3 C4 124.6(4) . . ?
O1 C3 C4 112.8(4) . . ?
C8 C4 N1 122.3(4) . . ?
C8 C4 C3 117.9(4) . . ?
N1 C4 C3 119.6(4) . . ?
N1 C5 N2 123.2(4) . . ?
N1 C5 H5 118.4 . . ?
N2 C5 H5 118.4 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 C9 134.6(4) . . ?
C4 C8 H8 112.7 . . ?
C9 C8 H8 112.7 . . ?
C10 C9 C14 118.0(4) . . ?
C10 C9 C8 127.1(4) . . ?
C14 C9 C8 114.9(4) . . ?
O3 C10 C9 123.3(4) . . ?
O3 C10 C11 115.4(4) . . ?
C9 C10 C11 121.3(4) . . ?
C12 C11 C10 117.4(4) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
C11 C12 O5 127.8(4) . . ?
C11 C12 C13 122.4(4) . . ?
O5 C12 C13 109.7(4) . . ?
C14 C13 C12 121.1(4) . . ?
C14 C13 O4 128.7(4) . . ?
C12 C13 O4 110.3(4) . . ?
C13 C14 C9 119.8(4) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
O4 C15 O5 109.2(4) . . ?
O4 C15 H15A 109.8 . . ?
O5 C15 H15A 109.8 . . ?
O4 C15 H15B 109.8 . . ?
O5 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C5 N1 C4 121.7(4) . . ?
C5 N2 C7 120.4(4) . . ?
C5 N2 C6 121.7(4) . . ?
C7 N2 C6 117.8(4) . . ?
C3 O1 C2 116.4(4) . . ?
C10 O3 H3 109.5 . . ?
C13 O4 C15 105.2(4) . . ?
C12 O5 C15 105.6(4) . . ?

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.088



####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 2076653'
loop_
_audit_author_name
_audit_author_address
'Yao Liu'
;Jiangxi normal university
China
;
_audit_update_record             
;
2021-04-11 deposited with the CCDC.	2024-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C13H10O6
_chemical_formula_sum            'C13 H10 O6'
_chemical_formula_weight         262.21

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'
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                   8.499(2)
_cell_length_b                   12.440(3)
_cell_length_c                   11.520(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.08(3)
_cell_angle_gamma                90
_cell_volume                     1181.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3142
_cell_measurement_theta_min      3.8090
_cell_measurement_theta_max      26.2820

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   0.7146
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9342
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.275
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2195
_reflns_number_gt                1509
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0686P)²+0.0847P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2195
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.4503(3) -0.1912(2) 0.7993(2) 0.0629(8) Uani 1 1 d . . . . .
H1A H 0.3327 -0.1902 0.7795 0.075 Uiso 1 1 calc R U . . .
H1B H 0.4850 -0.2492 0.7549 0.075 Uiso 1 1 calc R U . . .
C2 C 0.6151(2) -0.12346(18) 0.9631(2) 0.0452(6) Uani 1 1 d . . . . .
C3 C 0.6153(2) -0.05337(18) 0.86966(19) 0.0438(6) Uani 1 1 d . . . . .
C4 C 0.7073(2) 0.03772(17) 0.88105(19) 0.0427(6) Uani 1 1 d . . . . .
H4 H 0.7061 0.0836 0.8171 0.051 Uiso 1 1 calc R U . . .
C5 C 0.8040(2) 0.05698(16) 0.99660(18) 0.0363(5) Uani 1 1 d . . . . .
C6 C 0.8007(2) -0.01451(18) 1.08710(19) 0.0415(6) Uani 1 1 d . . . . .
C7 C 0.7080(3) -0.10774(19) 1.0764(2) 0.0481(6) Uani 1 1 d . . . . .
H7 H 0.7091 -0.1544 1.1396 0.058 Uiso 1 1 calc R U . . .
C8 C 0.9198(2) 0.13941(17) 1.04971(18) 0.0371(5) Uani 1 1 d . . . . .
C9 C 0.9748(3) 0.11151(18) 1.16642(19) 0.0454(6) Uani 1 1 d . . . . .
H9 H 1.0506 0.1510 1.2219 0.054 Uiso 1 1 calc R U . . .
C10 C 0.9644(2) 0.23036(17) 0.98690(19) 0.0420(6) Uani 1 1 d . . . . .
C11 C 1.0991(2) 0.30672(18) 1.0548(2) 0.0433(6) Uani 1 1 d . . . . .
C12 C 1.2455(3) 0.4660(2) 1.0424(2) 0.0607(7) Uani 1 1 d . . . . .
H12A H 1.3458 0.4317 1.0843 0.073 Uiso 1 1 calc R U . . .
H12B H 1.2038 0.5074 1.0997 0.073 Uiso 1 1 calc R U . . .
C13 C 1.2750(3) 0.5367(2) 0.9476(3) 0.0677(8) Uani 1 1 d . . . . .
H13A H 1.3266 0.4964 0.8961 0.101 Uiso 1 1 calc R U . . .
H13B H 1.3440 0.5950 0.9830 0.101 Uiso 1 1 calc R U . . .
H13C H 1.1736 0.5647 0.9017 0.101 Uiso 1 1 calc R U . . .
O1 O 0.5100(2) -0.09157(14) 0.76771(14) 0.0672(6) Uani 1 1 d . . . . .
O2 O 0.51109(19) -0.20795(13) 0.92346(16) 0.0615(5) Uani 1 1 d . . . . .
O3 O 0.90606(18) 0.01904(13) 1.19251(13) 0.0516(5) Uani 1 1 d . . . . .
O4 O 0.9010(2) 0.24924(14) 0.88291(14) 0.0639(6) Uani 1 1 d . . . . .
O5 O 1.1675(2) 0.29543(14) 1.15738(14) 0.0638(6) Uani 1 1 d . . . . .
O6 O 1.12689(18) 0.38464(13) 0.98564(15) 0.0554(5) 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 1.413(3) . ?
C1 O1 1.420(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.365(3) . ?
C2 O2 1.378(2) . ?
C2 C3 1.385(3) . ?
C3 C4 1.365(3) . ?
C3 O1 1.376(2) . ?
C4 C5 1.404(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 C8 1.450(3) . ?
C6 O3 1.386(2) . ?
C6 C7 1.391(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.357(3) . ?
C8 C10 1.442(3) . ?
C9 O3 1.357(3) . ?
C9 H9 0.9300 . ?
C10 O4 1.211(2) . ?
C10 C11 1.545(3) . ?
C11 O5 1.192(2) . ?
C11 O6 1.312(3) . ?
C12 O6 1.465(3) . ?
C12 C13 1.471(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 108.79(18) . . ?
O2 C1 H1A 109.9 . . ?
O1 C1 H1A 109.9 . . ?
O2 C1 H1B 109.9 . . ?
O1 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C7 C2 O2 126.9(2) . . ?
C7 C2 C3 122.9(2) . . ?
O2 C2 C3 110.17(19) . . ?
C4 C3 O1 127.4(2) . . ?
C4 C3 C2 123.8(2) . . ?
O1 C3 C2 108.80(19) . . ?
C3 C4 C5 115.0(2) . . ?
C3 C4 H4 122.5 . . ?
C5 C4 H4 122.5 . . ?
C6 C5 C4 119.55(19) . . ?
C6 C5 C8 105.91(17) . . ?
C4 C5 C8 134.5(2) . . ?
C5 C6 O3 109.97(19) . . ?
C5 C6 C7 126.0(2) . . ?
O3 C6 C7 124.1(2) . . ?
C2 C7 C6 112.8(2) . . ?
C2 C7 H7 123.6 . . ?
C6 C7 H7 123.6 . . ?
C9 C8 C10 128.93(19) . . ?
C9 C8 C5 105.79(19) . . ?
C10 C8 C5 125.27(18) . . ?
O3 C9 C8 111.92(18) . . ?
O3 C9 H9 124.0 . . ?
C8 C9 H9 124.0 . . ?
O4 C10 C8 122.69(19) . . ?
O4 C10 C11 118.6(2) . . ?
C8 C10 C11 118.75(18) . . ?
O5 C11 O6 124.9(2) . . ?
O5 C11 C10 123.5(2) . . ?
O6 C11 C10 111.58(18) . . ?
O6 C12 C13 107.73(19) . . ?
O6 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
O6 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
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 . . ?
C3 O1 C1 106.36(18) . . ?
C2 O2 C1 105.67(18) . . ?
C9 O3 C6 106.40(17) . . ?
C11 O6 C12 116.45(17) . . ?

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
C7 C2 C3 C4 0.0(4) . . . . ?
O2 C2 C3 C4 -179.6(2) . . . . ?
C7 C2 C3 O1 179.8(2) . . . . ?
O2 C2 C3 O1 0.3(3) . . . . ?
O1 C3 C4 C5 179.9(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 C8 178.7(2) . . . . ?
C4 C5 C6 O3 179.21(17) . . . . ?
C8 C5 C6 O3 0.5(2) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C8 C5 C6 C7 -178.9(2) . . . . ?
O2 C2 C7 C6 179.7(2) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
O3 C6 C7 C2 -179.5(2) . . . . ?
C6 C5 C8 C9 -0.5(2) . . . . ?
C4 C5 C8 C9 -179.0(2) . . . . ?
C6 C5 C8 C10 178.9(2) . . . . ?
C4 C5 C8 C10 0.4(4) . . . . ?
C10 C8 C9 O3 -179.0(2) . . . . ?
C5 C8 C9 O3 0.4(2) . . . . ?
C9 C8 C10 O4 -176.7(2) . . . . ?
C5 C8 C10 O4 4.0(3) . . . . ?
C9 C8 C10 C11 3.5(3) . . . . ?
C5 C8 C10 C11 -175.74(18) . . . . ?
O4 C10 C11 O5 179.3(2) . . . . ?
C8 C10 C11 O5 -1.0(3) . . . . ?
O4 C10 C11 O6 -0.4(3) . . . . ?
C8 C10 C11 O6 179.39(18) . . . . ?
C4 C3 O1 C1 176.8(2) . . . . ?
C2 C3 O1 C1 -3.0(3) . . . . ?
O2 C1 O1 C3 4.6(3) . . . . ?
C7 C2 O2 C1 -176.9(2) . . . . ?
C3 C2 O2 C1 2.6(2) . . . . ?
O1 C1 O2 C2 -4.4(3) . . . . ?
C8 C9 O3 C6 -0.1(2) . . . . ?
C5 C6 O3 C9 -0.2(2) . . . . ?
C7 C6 O3 C9 179.1(2) . . . . ?
O5 C11 O6 C12 -3.3(3) . . . . ?
C10 C11 O6 C12 176.38(19) . . . . ?
C13 C12 O6 C11 172.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 O5 0.93 2.26 2.830(3) 118.7 .
C7 H7 O5 0.93 2.40 3.225(3) 147.6 2_747
C4 H4 O4 0.93 2.64 3.101(3) 111.5 .
C1 H1A O4 0.97 2.49 3.289(3) 139.4 2_646
C9 H9 O5 0.93 2.26 2.830(3) 118.7 .
C1 H1A O4 0.97 2.49 3.289(3) 139.4 2_646
C7 H7 O5 0.93 2.40 3.225(3) 147.6 2_747
C4 H4 O4 0.93 2.64 3.101(3) 111.5 .
C9 H9 O5 0.93 2.26 2.830(3) 118.7 .
C1 H1A O4 0.97 2.49 3.289(3) 139.4 2_646
C7 H7 O5 0.93 2.40 3.225(3) 147.6 2_747
C4 H4 O4 0.93 2.64 3.101(3) 111.5 .

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.057



