# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

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

data_G23003
_audit_block_doi                 10.5517/ccdc.csd.cc2j3864
_database_code_depnum_ccdc_archive 'CCDC 2326835'
loop_
_audit_author_name
_audit_author_address
'Peter Mueller'
;MIT
United States of America
;
_audit_update_record             
;
2024-01-19 deposited with the CCDC.	2024-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.9523(6)
_cell_length_b                   13.5277(14)
_cell_length_c                   9.0395(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.324(3)
_cell_angle_gamma                90
_cell_volume                     705.24(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9479
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      78.76

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.105
_exptl_absorpt_coefficient_mu    0.684
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Photon3 CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4
_diffrn_reflns_number            28377
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.050
_diffrn_reflns_theta_max         78.975
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2997
_reflns_number_gt                2982
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    0.999

_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²+0.1511P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0233(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin.  Resonant signal is quite weak.
;
_refine_ls_abs_structure_Flack   0.3(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2997
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
O1 O 0.4276(2) 0.50272(10) 0.02715(14) 0.0274(3) Uani 1 1 d . . . . .
O2 O 0.0138(2) 0.49972(9) 0.38988(15) 0.0275(3) Uani 1 1 d . . . . .
N1 N 0.1849(2) 0.48908(11) 0.18826(16) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.3764(3) 0.52609(12) 0.14423(19) 0.0212(3) Uani 1 1 d . . . . .
C2 C 0.4969(3) 0.59878(12) 0.26289(19) 0.0208(3) Uani 1 1 d . . . . .
H2 H 0.668887 0.590569 0.297933 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4113(3) 0.70802(12) 0.22673(18) 0.0192(3) Uani 1 1 d . . . . .
H3 H 0.305298 0.718281 0.123274 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5952(3) 0.79013(13) 0.27948(18) 0.0225(4) Uani 1 1 d . . . . .
H4 H 0.721461 0.793502 0.224384 0.027 Uiso 1 1 calc R U . . .
C5 C 0.6724(3) 0.77086(14) 0.4516(2) 0.0289(4) Uani 1 1 d . . . . .
H5A H 0.780044 0.821898 0.507121 0.035 Uiso 1 1 calc R U . . .
H5B H 0.739019 0.704080 0.476637 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4535(3) 0.88391(13) 0.2778(2) 0.0260(4) Uani 1 1 d . . . . .
H6 H 0.439157 0.936731 0.206858 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3533(4) 0.87849(14) 0.3941(2) 0.0293(4) Uani 1 1 d . . . . .
H7 H 0.254879 0.926734 0.421441 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4259(4) 0.78075(14) 0.4747(2) 0.0284(4) Uani 1 1 d . . . . .
H8 H 0.411524 0.775969 0.582369 0.034 Uiso 1 1 calc R U . . .
C9 C 0.2879(3) 0.70337(12) 0.36136(19) 0.0217(3) Uani 1 1 d . . . . .
H9 H 0.116258 0.713859 0.331028 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3661(3) 0.59353(13) 0.39029(19) 0.0217(3) Uani 1 1 d . . . . .
H10 H 0.464255 0.578734 0.494763 0.026 Uiso 1 1 calc R U . . .
C11 C 0.1685(3) 0.52255(12) 0.33099(19) 0.0211(3) Uani 1 1 d . . . . .
C12 C 0.0090(3) 0.42677(13) 0.0894(2) 0.0237(4) Uani 1 1 d . . . . .
H12A H 0.020329 0.434598 -0.017407 0.028 Uiso 1 1 calc R U . . .
H12B H -0.146458 0.450122 0.094750 0.028 Uiso 1 1 calc R U . . .
C13 C 0.0310(3) 0.31837(13) 0.13077(18) 0.0208(3) Uani 1 1 d . . . . .
C14 C -0.1293(3) 0.27374(13) 0.19832(19) 0.0236(4) Uani 1 1 d . . . . .
H14 H -0.250873 0.312019 0.220321 0.028 Uiso 1 1 calc R U . . .
C15 C -0.1130(3) 0.17372(14) 0.2338(2) 0.0291(4) Uani 1 1 d . . . . .
H15 H -0.222752 0.143851 0.280337 0.035 Uiso 1 1 calc R U . . .
C16 C 0.0634(4) 0.11752(14) 0.2014(2) 0.0325(4) Uani 1 1 d . . . . .
H16 H 0.074857 0.049135 0.226032 0.039 Uiso 1 1 calc R U . . .
C17 C 0.2229(4) 0.16090(15) 0.1332(2) 0.0340(5) Uani 1 1 d . . . . .
H17 H 0.343105 0.122183 0.110208 0.041 Uiso 1 1 calc R U . . .
C18 C 0.2072(3) 0.26138(14) 0.0983(2) 0.0276(4) Uani 1 1 d . . . . .
H18 H 0.317334 0.291093 0.051974 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.213(2) . ?
O2 C11 1.212(2) . ?
N1 C1 1.390(2) . ?
N1 C11 1.393(2) . ?
N1 C12 1.464(2) . ?
C1 C2 1.500(2) . ?
C2 C10 1.543(2) . ?
C2 C3 1.571(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.550(2) . ?
C3 C9 1.571(2) . ?
C3 H3 1.0000 . ?
C4 C6 1.521(2) . ?
C4 C5 1.532(2) . ?
C4 H4 1.0000 . ?
C5 C8 1.538(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.332(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.520(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.550(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.560(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.511(2) . ?
C10 H10 1.0000 . ?
C12 C13 1.511(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.390(2) . ?
C13 C14 1.391(2) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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
C1 N1 C11 113.49(14) . . ?
C1 N1 C12 123.09(14) . . ?
C11 N1 C12 123.28(14) . . ?
O1 C1 N1 123.81(16) . . ?
O1 C1 C2 128.00(15) . . ?
N1 C1 C2 108.18(14) . . ?
C1 C2 C10 105.27(13) . . ?
C1 C2 C3 113.24(13) . . ?
C10 C2 C3 90.05(12) . . ?
C1 C2 H2 115.1 . . ?
C10 C2 H2 115.1 . . ?
C3 C2 H2 115.1 . . ?
C4 C3 C9 102.74(13) . . ?
C4 C3 C2 116.24(14) . . ?
C9 C3 C2 89.49(12) . . ?
C4 C3 H3 115.0 . . ?
C9 C3 H3 115.0 . . ?
C2 C3 H3 115.0 . . ?
C6 C4 C5 100.25(14) . . ?
C6 C4 C3 104.30(14) . . ?
C5 C4 C3 101.65(13) . . ?
C6 C4 H4 116.1 . . ?
C5 C4 H4 116.1 . . ?
C3 C4 H4 116.1 . . ?
C4 C5 C8 93.82(14) . . ?
C4 C5 H5A 113.0 . . ?
C8 C5 H5A 113.0 . . ?
C4 C5 H5B 113.0 . . ?
C8 C5 H5B 113.0 . . ?
H5A C5 H5B 110.4 . . ?
C7 C6 C4 107.56(16) . . ?
C7 C6 H6 126.2 . . ?
C4 C6 H6 126.2 . . ?
C6 C7 C8 107.25(16) . . ?
C6 C7 H7 126.4 . . ?
C8 C7 H7 126.4 . . ?
C7 C8 C5 100.25(15) . . ?
C7 C8 C9 103.25(15) . . ?
C5 C8 C9 102.64(14) . . ?
C7 C8 H8 116.1 . . ?
C5 C8 H8 116.1 . . ?
C9 C8 H8 116.1 . . ?
C8 C9 C10 116.42(15) . . ?
C8 C9 C3 102.24(13) . . ?
C10 C9 C3 89.45(12) . . ?
C8 C9 H9 115.1 . . ?
C10 C9 H9 115.1 . . ?
C3 C9 H9 115.1 . . ?
C11 C10 C2 104.88(13) . . ?
C11 C10 C9 111.83(14) . . ?
C2 C10 C9 90.92(12) . . ?
C11 C10 H10 115.4 . . ?
C2 C10 H10 115.4 . . ?
C9 C10 H10 115.4 . . ?
O2 C11 N1 123.99(16) . . ?
O2 C11 C10 128.00(16) . . ?
N1 C11 C10 107.94(14) . . ?
N1 C12 C13 113.73(13) . . ?
N1 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N1 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C18 C13 C14 119.16(15) . . ?
C18 C13 C12 120.64(15) . . ?
C14 C13 C12 120.18(15) . . ?
C15 C14 C13 120.53(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.95(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.08(18) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.94(18) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.34(18) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_G23002
_audit_block_doi                 10.5517/ccdc.csd.cc2j3875
_database_code_depnum_ccdc_archive 'CCDC 2326836'
loop_
_audit_author_name
_audit_author_address
'Peter Mueller'
;MIT
United States of America
;
_audit_update_record             
;
2024-01-19 deposited with the CCDC.	2024-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.5018(6)
_cell_length_b                   10.4685(7)
_cell_length_c                   9.0020(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.336(4)
_cell_angle_gamma                90
_cell_volume                     671.06(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      5.18
_cell_measurement_theta_max      78.14

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    0.718
_shelx_estimated_absorpt_T_min   0.720
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5585
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Photon3 CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4
_diffrn_reflns_number            14537
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.176
_diffrn_reflns_theta_max         78.467
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1506
_reflns_number_gt                1374
_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       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Kappa DUO four-circle diffractometer, Bruker Photon3 CPAD. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0645P)²+0.4361P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1506
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
O1 O 0.62364(17) 0.53195(10) 0.70263(13) 0.0297(3) Uani 1 1 d . . . . .
N1 N 0.6317(2) 0.750000 0.6703(2) 0.0209(4) Uani 1 2 d S T P . .
C1 C 0.6383(2) 0.63845(13) 0.75733(18) 0.0231(4) Uani 1 1 d . . . . .
C2 C 0.6655(2) 0.67650(13) 0.92464(17) 0.0226(3) Uani 1 1 d . . . . .
H2 H 0.781496 0.639165 1.000161 0.027 Uiso 1 1 calc R U . . .
C3 C 0.4921(2) 0.67511(13) 0.98810(17) 0.0222(3) Uani 1 1 d . . . . .
H3 H 0.522793 0.637960 1.095565 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2903(2) 0.64202(14) 0.88258(18) 0.0234(4) Uani 1 1 d . . . . .
H4 H 0.268681 0.552649 0.841607 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2439(3) 0.750000 0.7601(2) 0.0234(5) Uani 1 2 d S T P . .
H5A H 0.326989 0.750001 0.693714 0.028 Uiso 1 2 calc R U P . .
H5B H 0.110521 0.750000 0.694018 0.028 Uiso 1 2 calc R U P . .
C6 C 0.1733(2) 0.68636(15) 0.98319(18) 0.0262(4) Uani 1 1 d . . . . .
H6 H 0.111221 0.632890 1.036602 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5770(3) 0.750000 0.4983(2) 0.0220(4) Uani 1 2 d S T P . .
H7A H 0.499164 0.826400 0.457675 0.026 Uiso 0.5 1 calc R U P . .
H7B H 0.499164 0.673600 0.457674 0.026 Uiso 0.5 1 calc R U P . .
C8 C 0.7434(3) 0.750000 0.4378(2) 0.0204(4) Uani 1 2 d S T P . .
C9 C 0.8208(2) 0.86481(14) 0.40920(18) 0.0248(4) Uani 1 1 d . . . . .
H9 H 0.767369 0.943555 0.426242 0.030 Uiso 1 1 calc R U . . .
C10 C 0.9755(2) 0.86477(16) 0.35598(19) 0.0295(4) Uani 1 1 d . . . . .
H10 H 1.027771 0.943382 0.337025 0.035 Uiso 1 1 calc R U . . .
C11 C 1.0539(3) 0.750000 0.3304(3) 0.0293(5) Uani 1 2 d S T P . .
H11 H 1.160948 0.749999 0.295482 0.035 Uiso 1 2 calc R U P . .


_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
O1 C1 1.2098(18) . ?
N1 C1 1.3983(17) . ?
N1 C1 1.3983(17) 4_575 ?
N1 C7 1.472(3) . ?
C1 C2 1.509(2) . ?
C2 C2 1.539(3) 4_575 ?
C2 C3 1.577(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.552(2) . ?
C3 C3 1.568(3) 4_575 ?
C3 H3 1.0000 . ?
C4 C6 1.519(2) . ?
C4 C5 1.541(2) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C6 1.332(3) 4_575 ?
C6 H6 0.9500 . ?
C7 C8 1.511(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.3934(18) . ?
C8 C9 1.3934(18) 4_575 ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?

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
C1 N1 C1 113.25(18) . 4_575 ?
C1 N1 C7 122.57(9) . . ?
C1 N1 C7 122.57(9) 4_575 . ?
O1 C1 N1 123.98(14) . . ?
O1 C1 C2 128.04(14) . . ?
N1 C1 C2 107.98(13) . . ?
C1 C2 C2 105.31(8) . 4_575 ?
C1 C2 C3 119.45(12) . . ?
C2 C2 C3 90.53(7) 4_575 . ?
C1 C2 H2 113.0 . . ?
C2 C2 H2 113.0 4_575 . ?
C3 C2 H2 113.0 . . ?
C4 C3 C3 102.90(7) . 4_575 ?
C4 C3 C2 122.49(12) . . ?
C3 C3 C2 89.47(7) 4_575 . ?
C4 C3 H3 112.9 . . ?
C3 C3 H3 112.9 4_575 . ?
C2 C3 H3 112.9 . . ?
C6 C4 C5 99.18(13) . . ?
C6 C4 C3 101.66(12) . . ?
C5 C4 C3 103.41(12) . . ?
C6 C4 H4 116.7 . . ?
C5 C4 H4 116.7 . . ?
C3 C4 H4 116.7 . . ?
C4 C5 C4 94.40(16) 4_575 . ?
C4 C5 H5A 112.8 4_575 . ?
C4 C5 H5A 112.8 . . ?
C4 C5 H5B 112.8 4_575 . ?
C4 C5 H5B 112.8 . . ?
H5A C5 H5B 110.3 . . ?
C6 C6 C4 107.80(8) 4_575 . ?
C6 C6 H6 126.1 4_575 . ?
C4 C6 H6 126.1 . . ?
N1 C7 C8 112.99(17) . . ?
N1 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C9 119.2(2) . 4_575 ?
C9 C8 C7 120.40(10) . . ?
C9 C8 C7 120.40(10) 4_575 . ?
C10 C9 C8 120.37(15) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.10(15) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C10 119.8(2) . 4_575 ?
C10 C11 H11 120.1 . . ?
C10 C11 H11 120.1 4_575 . ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_P23127
_database_code_depnum_ccdc_archive 'CCDC 2351614'
loop_
_audit_author_name
_audit_author_address
Peter
;MIT
United States of America
;
_audit_update_record             
;
2024-04-27 deposited with the CCDC.	2024-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 O5'
_chemical_formula_weight         222.19

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                   7.9853(11)
_cell_length_b                   11.7489(17)
_cell_length_c                   10.3831(15)
_cell_angle_alpha                90
_cell_angle_beta                 103.886(6)
_cell_angle_gamma                90
_cell_volume                     945.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9791
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      31.55

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5743
_exptl_absorpt_correction_T_max  0.6748
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Photon3 CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4
_diffrn_reflns_number            39227
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.627
_diffrn_reflns_theta_max         31.552
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3157
_reflns_number_gt                2725
_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       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Kappa DUO four-circle diffractometer, Bruker Photon3 CPAD. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0617P)²+0.6425P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3157
_refine_ls_number_parameters     151
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
O1 O 0.11077(13) 0.62545(8) 0.80674(10) 0.0223(2) Uani 1 1 d . . . . .
O2 O -0.10743(11) 0.54802(8) 0.65798(10) 0.01944(19) Uani 1 1 d D . . . .
H2 H -0.122(3) 0.4863(14) 0.6138(18) 0.029 Uiso 1 1 d D U . . .
O3 O -0.14246(11) 0.35952(8) 0.51594(9) 0.01880(19) Uani 1 1 d . . . . .
O4 O 0.03724(11) 0.22192(8) 0.48088(9) 0.01843(19) Uani 1 1 d D . . . .
H4 H -0.051(2) 0.2017(15) 0.4182(16) 0.022 Uiso 1 1 d D U . . .
O5 O 0.75903(11) 0.35296(8) 0.80711(9) 0.0200(2) Uani 1 1 d . . . . .
C1 C 0.04986(15) 0.54434(10) 0.73917(12) 0.0167(2) Uani 1 1 d . . . . .
C2 C 0.14881(14) 0.43714(10) 0.74075(11) 0.0152(2) Uani 1 1 d . . . . .
C3 C 0.32024(14) 0.40125(10) 0.82896(11) 0.0154(2) Uani 1 1 d . . . . .
H3 H 0.318440 0.384580 0.923063 0.018 Uiso 1 1 calc R U . . .
C4 C 0.48605(14) 0.46033(10) 0.81036(12) 0.0163(2) Uani 1 1 d . . . . .
H4A H 0.502235 0.541498 0.839679 0.020 Uiso 1 1 calc R U . . .
C5 C 0.62547(15) 0.37719(10) 0.87928(12) 0.0173(2) Uani 1 1 d . . . . .
H5 H 0.650043 0.366016 0.977515 0.021 Uiso 1 1 calc R U . . .
C6 C 0.60935(15) 0.27842(11) 0.78995(12) 0.0182(2) Uani 1 1 d . . . . .
H6 H 0.622526 0.199518 0.827126 0.022 Uiso 1 1 calc R U . . .
C7 C 0.46026(15) 0.30688(11) 0.67186(12) 0.0180(2) Uani 1 1 d . . . . .
H7 H 0.455581 0.263190 0.588419 0.022 Uiso 1 1 calc R U . . .
C8 C 0.30351(14) 0.29260(10) 0.73494(12) 0.0158(2) Uani 1 1 d . . . . .
H8 H 0.295848 0.217689 0.778899 0.019 Uiso 1 1 calc R U . . .
C9 C 0.13316(14) 0.34384(10) 0.66260(12) 0.0154(2) Uani 1 1 d . . . . .
C10 C -0.00370(14) 0.30882(10) 0.54656(12) 0.0159(2) Uani 1 1 d . . . . .
C11 C 0.47671(15) 0.43739(11) 0.66281(12) 0.0181(2) Uani 1 1 d . . . . .
H11A H 0.582898 0.460878 0.636594 0.022 Uiso 1 1 calc R U . . .
H11B H 0.374394 0.472685 0.603175 0.022 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2137(15) . ?
O2 C1 1.3349(14) . ?
O2 H2 0.851(15) . ?
O3 C10 1.2307(14) . ?
O4 C10 1.3120(15) . ?
O4 H4 0.868(14) . ?
O5 C6 1.4577(15) . ?
O5 C5 1.4709(16) . ?
C1 C2 1.4848(16) . ?
C2 C9 1.3517(16) . ?
C2 C3 1.5129(15) . ?
C3 C4 1.5475(16) . ?
C3 C8 1.5930(17) . ?
C3 H3 1.0000 . ?
C4 C5 1.5243(16) . ?
C4 C11 1.5396(17) . ?
C4 H4A 1.0000 . ?
C5 C6 1.4717(17) . ?
C5 H5 1.0000 . ?
C6 C7 1.5270(16) . ?
C6 H6 1.0000 . ?
C7 C11 1.5437(18) . ?
C7 C8 1.5548(17) . ?
C7 H7 1.0000 . ?
C8 C9 1.5121(16) . ?
C8 H8 1.0000 . ?
C9 C10 1.4776(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
C1 O2 H2 107.5(14) . . ?
C10 O4 H4 110.1(12) . . ?
C6 O5 C5 60.33(8) . . ?
O1 C1 O2 121.70(11) . . ?
O1 C1 C2 121.42(11) . . ?
O2 C1 C2 116.87(10) . . ?
C9 C2 C1 135.15(11) . . ?
C9 C2 C3 94.43(9) . . ?
C1 C2 C3 130.16(10) . . ?
C2 C3 C4 118.45(10) . . ?
C2 C3 C8 85.51(8) . . ?
C4 C3 C8 103.38(9) . . ?
C2 C3 H3 115.0 . . ?
C4 C3 H3 115.0 . . ?
C8 C3 H3 115.0 . . ?
C5 C4 C11 102.15(10) . . ?
C5 C4 C3 101.79(9) . . ?
C11 C4 C3 101.95(9) . . ?
C5 C4 H4A 116.2 . . ?
C11 C4 H4A 116.2 . . ?
C3 C4 H4A 116.2 . . ?
O5 C5 C6 59.39(8) . . ?
O5 C5 C4 114.96(10) . . ?
C6 C5 C4 105.41(9) . . ?
O5 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
O5 C6 C5 60.28(8) . . ?
O5 C6 C7 115.15(10) . . ?
C5 C6 C7 105.48(10) . . ?
O5 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C11 101.83(9) . . ?
C6 C7 C8 100.92(10) . . ?
C11 C7 C8 102.81(9) . . ?
C6 C7 H7 116.3 . . ?
C11 C7 H7 116.3 . . ?
C8 C7 H7 116.3 . . ?
C9 C8 C7 117.84(10) . . ?
C9 C8 C3 85.33(8) . . ?
C7 C8 C3 102.36(9) . . ?
C9 C8 H8 115.5 . . ?
C7 C8 H8 115.5 . . ?
C3 C8 H8 115.5 . . ?
C2 C9 C10 131.23(11) . . ?
C2 C9 C8 94.71(9) . . ?
C10 C9 C8 134.05(11) . . ?
O3 C10 O4 124.30(11) . . ?
O3 C10 C9 121.31(11) . . ?
O4 C10 C9 114.38(10) . . ?
C4 C11 C7 95.61(9) . . ?
C4 C11 H11A 112.6 . . ?
C7 C11 H11A 112.6 . . ?
C4 C11 H11B 112.6 . . ?
C7 C11 H11B 112.6 . . ?
H11A C11 H11B 110.1 . . ?

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
_geom_hbond_publ_flag
O2 H2 O3 0.851(15) 1.789(15) 2.6382(14) 176(2) . yes
O4 H4 O5 0.868(14) 1.791(15) 2.6535(13) 171.6(18) 4_465 yes
C5 H5 O1 1.00 2.57 3.4306(16) 143.7 3_667 yes
C6 H6 O3 1.00 2.47 3.1350(15) 123.9 4_666 yes

_refine_diff_density_max         0.478
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.064

