# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_24dhba
_database_code_depnum_ccdc_archive 'CCDC 2465472'
loop_
_audit_author_name
_audit_author_address
'Toshiyuki Sasaki'
; Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2025-06-19 deposited with the CCDC.	2025-08-27 downloaded from the CCDC.
;
_audit_creation_date             2025-06-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3

# start Validation Reply Form
_vrf_RINTA01_24dhba              
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: This dataset was merged from 13 crystals.
R(int) increases with the multiplicity of the dataset.
This is pointed out in Diederichs & Karplus,
Nat. Struct. Biol., 1997 for the case of a related metric R(merge)
in macromolecular crystallography.
;
_vrf_PLAT020_24dhba              
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.294 Report
RESPONSE: 
This dataset was merged from 13 crystals.
R(int) increases with the multiplicity of the dataset.
This is pointed out in Diederichs & Karplus,
Nat. Struct. Biol., 1997 for the case of a related metric R(merge)
in macromolecular crystallography.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H6 O4'
_chemical_formula_sum            'C7 H6 O4'
_chemical_formula_weight         154.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   3.6740(6)
_cell_length_b                   22.230(2)
_cell_length_c                   8.0598(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.801(15)
_cell_angle_gamma                90
_cell_volume                     648.65(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8916
_cell_measurement_temperature    79
_cell_measurement_theta_max      1.2593825225381257
_cell_measurement_theta_min      0.13283470852102497
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       powder
_exptl_crystal_F_000             112
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2938
_diffrn_reflns_av_unetI/netI     0.1901
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            43188
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        0.862
_diffrn_reflns_theta_max         1.197
_diffrn_reflns_theta_min         0.133
_diffrn_ambient_temperature      79
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.991
_diffrn_detector                 
;
Falcon 3 direct electron camera (integration mode)
;
_diffrn_detector_type            CMOS
_diffrn_measurement_device_type  'Talos Arctica electron microscope'
_diffrn_measurement_method       
;
continuous rotation electron diffraction (MicroED)
;
_diffrn_radiation_probe          electron
_diffrn_radiation_type           electron
_diffrn_radiation_wavelength     0.02508
_diffrn_source                   'Talos Arctica Field Emission Gun'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2013
_reflns_number_total             3114
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'dials.two_theta_refine (Waterman et al., 2016)'
_computing_data_collection       'SerialEM (Mastronarde, 2005)'
_computing_data_reduction        'dials.scale (Beilsten-Edmands et al., 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       85926(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         3114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2006
_refine_ls_R_factor_gt           0.1661
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1654P)²+0.0891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4061
_refine_ls_wR_factor_ref         0.4185
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C3(H3)
2.b Idealised tetrahedral OH refined as rotating group:
 O11(H11), O10(H10), O8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O11 O 0.6171(11) 0.29373(14) 0.3545(4) 0.0270(7) Uani 1 1 d . . . . .
H11 H 0.672144 0.259293 0.393858 0.041 Uiso 1 1 calc R U . . .
O10 O 0.3768(11) 0.32243(13) 0.9146(4) 0.0266(7) Uani 1 1 d . . . . .
H10 H 0.322617 0.349990 0.977449 0.040 Uiso 1 1 calc R U . . .
O8 O 0.1042(11) 0.50097(13) 0.7889(4) 0.0254(7) Uani 1 1 d . . . . .
H8 H 0.039462 0.521470 0.866421 0.038 Uiso 1 1 calc R U . . .
C7 C 0.1765(13) 0.44630(16) 0.8413(5) 0.0237(8) Uani 1 1 d . . . . .
O9 O 0.1486(11) 0.42980(13) 0.9870(4) 0.0258(7) Uani 1 1 d . . . . .
C5 C 0.4263(13) 0.38853(16) 0.4327(5) 0.0240(8) Uani 1 1 d . . . . .
H5 H 0.437328 0.403149 0.322870 0.029 Uiso 1 1 calc R U . . .
C2 C 0.3896(12) 0.34519(16) 0.7591(5) 0.0210(8) Uani 1 1 d . . . . .
C6 C 0.3205(12) 0.42576(16) 0.5519(5) 0.0231(8) Uani 1 1 d . . . . .
H6 H 0.260798 0.466433 0.522966 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5174(13) 0.32886(17) 0.4753(5) 0.0248(9) Uani 1 1 d . . . . .
C1 C 0.2972(12) 0.40552(17) 0.7172(5) 0.0227(8) Uani 1 1 d . . . . .
C3 C 0.5031(12) 0.30697(17) 0.6388(5) 0.0239(8) Uani 1 1 d . . . . .
H3 H 0.570029 0.266517 0.667263 0.029 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
O11 H11 0.8400 . ?
O11 C4 1.347(5) . ?
O10 H10 0.8400 . ?
O10 C2 1.360(5) . ?
O8 H8 0.8400 . ?
O8 C7 1.299(5) . ?
C7 O9 1.251(5) . ?
C7 C1 1.473(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.373(5) . ?
C5 C4 1.397(5) . ?
C2 C1 1.410(5) . ?
C2 C3 1.404(5) . ?
C6 H6 0.9500 . ?
C6 C1 1.423(5) . ?
C4 C3 1.414(5) . ?
C3 H3 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
C4 O11 H11 109.5 . . ?
C2 O10 H10 109.5 . . ?
C7 O8 H8 109.5 . . ?
O8 C7 C1 115.0(3) . . ?
O9 C7 O8 122.3(3) . . ?
O9 C7 C1 122.6(3) . . ?
C6 C5 H5 120.5 . . ?
C6 C5 C4 119.0(4) . . ?
C4 C5 H5 120.5 . . ?
O10 C2 C1 122.0(3) . . ?
O10 C2 C3 118.2(3) . . ?
C3 C2 C1 119.8(3) . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C1 122.3(3) . . ?
C1 C6 H6 118.9 . . ?
O11 C4 C5 117.1(4) . . ?
O11 C4 C3 122.2(4) . . ?
C5 C4 C3 120.7(3) . . ?
C2 C1 C7 120.7(3) . . ?
C2 C1 C6 118.3(3) . . ?
C6 C1 C7 121.0(3) . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?

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
O11 C4 C3 C2 -178.6(4) . . . . ?
O10 C2 C1 C7 -0.9(7) . . . . ?
O10 C2 C1 C6 179.6(4) . . . . ?
O10 C2 C3 C4 179.6(4) . . . . ?
O8 C7 C1 C2 179.0(4) . . . . ?
O8 C7 C1 C6 -1.5(6) . . . . ?
O9 C7 C1 C2 -0.4(7) . . . . ?
O9 C7 C1 C6 179.1(5) . . . . ?
C5 C6 C1 C7 -178.9(4) . . . . ?
C5 C6 C1 C2 0.6(7) . . . . ?
C5 C4 C3 C2 1.2(7) . . . . ?
C6 C5 C4 O11 179.5(4) . . . . ?
C6 C5 C4 C3 -0.3(7) . . . . ?
C4 C5 C6 C1 -0.6(7) . . . . ?
C1 C2 C3 C4 -1.2(7) . . . . ?
C3 C2 C1 C7 179.8(4) . . . . ?
C3 C2 C1 C6 0.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_urea-24dhba-pre
_database_code_depnum_ccdc_archive 'CCDC 2465561'
loop_
_audit_author_name
_audit_author_address
'Toshiyuki Sasaki'
; Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2025-06-19 deposited with the CCDC.	2025-08-27 downloaded from the CCDC.
;
_audit_creation_date             2025-06-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C H4 N2 O), C7 H6 O4'
_chemical_formula_sum            'C9 H14 N4 O6'
_chemical_formula_weight         274.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2558(10)
_cell_length_b                   8.8651(16)
_cell_length_c                   10.860(2)
_cell_angle_alpha                74.412(15)
_cell_angle_beta                 75.956(14)
_cell_angle_gamma                71.464(14)
_cell_volume                     628.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8666
_cell_measurement_temperature    79
_cell_measurement_theta_max      1.1171058736815767
_cell_measurement_theta_min      0.13786914567765718
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       powder
_exptl_crystal_F_000             99
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2278
_diffrn_reflns_av_unetI/netI     0.1231
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            47366
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        0.862
_diffrn_reflns_theta_max         0.984
_diffrn_reflns_theta_min         0.116
_diffrn_ambient_temperature      79
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_detector                 
;
Falcon 3 direct electron camera (integration mode)
;
_diffrn_detector_type            CMOS
_diffrn_measurement_device_type  'Talos Arctica electron microscope'
_diffrn_measurement_method       
;
continuous rotation electron diffraction (MicroED)
;
_diffrn_radiation_probe          electron
_diffrn_radiation_type           electron
_diffrn_radiation_wavelength     0.02508
_diffrn_source                   'Talos Arctica Field Emission Gun'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2195
_reflns_number_total             3360
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'dials.two_theta_refine (Waterman et al., 2016)'
_computing_data_collection       'SerialEM (Mastronarde, 2005)'
_computing_data_reduction        'dials.scale (Beilsten-Edmands et al., 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       21014(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.1927
_refine_ls_R_factor_gt           0.1591
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1554P)²+0.2722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4008
_refine_ls_wR_factor_ref         0.4139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(O10) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.05 and sigma for 1-3 distances of 0.05
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C3(H3)
4.b X=CH2 refined with riding coordinates:
 N14(H14A,H14B), N15(H15A,H15B), N18(H18A,H18B), N19(H19A,H19B)
4.c Idealised tetrahedral OH refined as rotating group:
 O11(H11), O9(H9), O10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N14 N 0.9506(7) 0.3173(7) -0.0175(5) 0.0263(13) Uani 1 1 d . . . . .
H14A H 0.843867 0.285049 0.020555 0.032 Uiso 1 1 calc R U . . .
H14B H 0.947883 0.394509 -0.088200 0.032 Uiso 1 1 calc R U . . .
N15 N 1.2803(7) 0.2961(7) -0.0289(5) 0.0256(13) Uani 1 1 d . . . . .
H15A H 1.391018 0.249467 0.002065 0.031 Uiso 1 1 calc R U . . .
H15B H 1.277000 0.373278 -0.099621 0.031 Uiso 1 1 calc R U . . .
O17 O 0.3884(7) 0.8035(7) 0.8816(5) 0.0285(13) Uani 1 1 d . . . . .
O11 O 0.5727(8) 0.4994(7) 0.8534(5) 0.0301(12) Uani 1 1 d . . . . .
H11 H 0.537711 0.600108 0.849911 0.045 Uiso 1 1 calc R U . . .
O13 O 1.1247(7) 0.1395(7) 0.1318(5) 0.0280(12) Uani 1 1 d . . . . .
N18 N 0.5221(8) 0.9987(7) 0.7429(6) 0.0355(16) Uani 1 1 d . . . . .
H18A H 0.640653 0.944226 0.760223 0.043 Uiso 1 1 calc R U . . .
H18B H 0.504923 1.092609 0.687245 0.043 Uiso 1 1 calc R U . . .
C5 C 0.7355(9) 0.3085(8) 0.7226(6) 0.0243(14) Uani 1 1 d . . . . .
H5 H 0.739682 0.223950 0.798096 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6489(9) 0.4708(8) 0.7352(6) 0.0275(15) Uani 1 1 d . . . . .
O8 O 0.8863(8) 0.4628(7) 0.2620(5) 0.0316(13) Uani 1 1 d . . . . .
O9 O 0.9695(9) 0.2037(7) 0.3609(5) 0.0374(14) Uani 1 1 d . . . . .
H9 H 1.018740 0.192053 0.284444 0.056 Uiso 1 1 calc R U . . .
C16 C 0.3688(8) 0.9389(7) 0.8007(6) 0.0220(14) Uani 1 1 d . . . . .
O10 O 0.7070(8) 0.6784(7) 0.3966(5) 0.0307(13) Uani 1 1 d . U . . .
H10 H 0.754307 0.639058 0.329782 0.046 Uiso 1 1 calc R U . . .
N19 N 0.1924(8) 1.0235(7) 0.7701(6) 0.0384(17) Uani 1 1 d . . . . .
H19A H 0.088977 0.985776 0.805884 0.046 Uiso 1 1 calc R U . . .
H19B H 0.179337 1.117131 0.714154 0.046 Uiso 1 1 calc R U . . .
C7 C 0.8923(9) 0.3549(8) 0.3614(6) 0.0243(14) Uani 1 1 d . . . . .
C12 C 1.1162(9) 0.2492(8) 0.0317(6) 0.0253(14) Uani 1 1 d . U . . .
C2 C 0.7200(9) 0.5565(8) 0.5035(6) 0.0257(15) Uani 1 1 d . . . . .
C6 C 0.8139(9) 0.2705(8) 0.6036(6) 0.0263(15) Uani 1 1 d . . . . .
H6 H 0.872482 0.160022 0.597126 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6427(9) 0.5944(8) 0.6248(6) 0.0247(14) Uani 1 1 d . . . . .
H3 H 0.585586 0.704592 0.632348 0.030 Uiso 1 1 calc R U . . .
C1 C 0.8084(9) 0.3948(8) 0.4896(6) 0.0246(14) 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
N14 H14A 0.8800 . ?
N14 H14B 0.8800 . ?
N14 C12 1.331(8) . ?
N15 H15A 0.8800 . ?
N15 H15B 0.8800 . ?
N15 C12 1.346(7) . ?
O17 C16 1.272(7) . ?
O11 H11 0.8400 . ?
O11 C4 1.326(9) . ?
O13 C12 1.248(7) . ?
N18 H18A 0.8800 . ?
N18 H18B 0.8800 . ?
N18 C16 1.330(8) . ?
C5 H5 0.9500 . ?
C5 C4 1.405(9) . ?
C5 C6 1.365(9) . ?
C4 C3 1.389(8) . ?
O8 C7 1.235(7) . ?
O9 H9 0.8400 . ?
O9 C7 1.279(9) . ?
C16 N19 1.331(8) . ?
O10 H10 0.8400 . ?
O10 C2 1.356(7) . ?
N19 H19A 0.8800 . ?
N19 H19B 0.8800 . ?
C7 C1 1.467(9) . ?
C2 C3 1.386(9) . ?
C2 C1 1.404(9) . ?
C6 H6 0.9500 . ?
C6 C1 1.419(8) . ?
C3 H3 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
H14A N14 H14B 120.0 . . ?
C12 N14 H14A 120.0 . . ?
C12 N14 H14B 120.0 . . ?
H15A N15 H15B 120.0 . . ?
C12 N15 H15A 120.0 . . ?
C12 N15 H15B 120.0 . . ?
C4 O11 H11 109.5 . . ?
H18A N18 H18B 120.0 . . ?
C16 N18 H18A 120.0 . . ?
C16 N18 H18B 120.0 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C6 C5 C4 121.0(6) . . ?
O11 C4 C5 118.0(6) . . ?
O11 C4 C3 122.5(6) . . ?
C3 C4 C5 119.4(6) . . ?
C7 O9 H9 109.5 . . ?
O17 C16 N18 121.6(5) . . ?
O17 C16 N19 120.2(5) . . ?
N18 C16 N19 118.2(5) . . ?
C2 O10 H10 109.5 . . ?
C16 N19 H19A 120.0 . . ?
C16 N19 H19B 120.0 . . ?
H19A N19 H19B 120.0 . . ?
O8 C7 O9 123.5(7) . . ?
O8 C7 C1 120.8(6) . . ?
O9 C7 C1 115.7(5) . . ?
N14 C12 N15 119.7(5) . . ?
O13 C12 N14 121.5(5) . . ?
O13 C12 N15 118.8(5) . . ?
O10 C2 C3 119.0(6) . . ?
O10 C2 C1 119.7(6) . . ?
C3 C2 C1 121.3(6) . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C1 120.4(6) . . ?
C1 C6 H6 119.8 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.9(6) . . ?
C2 C3 H3 120.1 . . ?
C2 C1 C7 121.3(5) . . ?
C2 C1 C6 118.0(6) . . ?
C6 C1 C7 120.7(6) . . ?

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
O11 C4 C3 C2 -178.2(6) . . . . ?
C5 C4 C3 C2 0.6(9) . . . . ?
C5 C6 C1 C7 180.0(6) . . . . ?
C5 C6 C1 C2 -0.1(9) . . . . ?
C4 C5 C6 C1 -0.3(9) . . . . ?
O8 C7 C1 C2 -0.5(9) . . . . ?
O8 C7 C1 C6 179.4(6) . . . . ?
O9 C7 C1 C2 179.7(6) . . . . ?
O9 C7 C1 C6 -0.4(9) . . . . ?
O10 C2 C3 C4 177.9(6) . . . . ?
O10 C2 C1 C7 1.7(9) . . . . ?
O10 C2 C1 C6 -178.2(5) . . . . ?
C6 C5 C4 O11 179.0(6) . . . . ?
C6 C5 C4 C3 0.1(9) . . . . ?
C3 C2 C1 C7 -179.3(5) . . . . ?
C3 C2 C1 C6 0.9(9) . . . . ?
C1 C2 C3 C4 -1.1(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_urea-24dhba-post
_database_code_depnum_ccdc_archive 'CCDC 2465562'
loop_
_audit_author_name
_audit_author_address
'Toshiyuki Sasaki'
; Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2025-06-19 deposited with the CCDC.	2025-08-27 downloaded from the CCDC.
;
_audit_creation_date             2025-06-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3

# start Validation Reply Form
_vrf_RINTA01_urea-24dhba-post    
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: This dataset was merged from 21 crystals.
R(int) increases with the multiplicity of the dataset.
This is pointed out in Diederichs & Karplus,
Nat. Struct. Biol., 1997 for the case of a related metric R(merge)
in macromolecular crystallography.
;
_vrf_PLAT020_urea-24dhba-post    
;
PROBLEM: The Value of Rint is greater Than 0.12 .........      0.336 Report
RESPONSE: 
This dataset was merged from 21 crystals.
R(int) increases with the multiplicity of the dataset.
This is pointed out in Diederichs & Karplus,
Nat. Struct. Biol., 1997 for the case of a related metric R(merge)
in macromolecular crystallography.
;
_vrf_PLAT084_urea-24dhba-post    
;
PROBLEM: High wR2 Value (i.e. > 0.25) .........      0.47 Report
RESPONSE: 
Such a high wR2 value, while typical 
for electron diffraction data refined with a kinematic model, 
was likely exacerbated by the aggregation 
of the crystal particles in our sample.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H6 O4, C H4 N2 O'
_chemical_formula_sum            'C8 H10 N2 O5'
_chemical_formula_weight         214.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.9711(15)
_cell_length_b                   11.059(3)
_cell_length_c                   31.307(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.70(2)
_cell_angle_gamma                90
_cell_volume                     2412.6(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4205
_cell_measurement_temperature    79
_cell_measurement_theta_max      0.8684896833716158
_cell_measurement_theta_min      0.12253341769976006
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       powder
_exptl_crystal_F_000             310
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.3357
_diffrn_reflns_av_unetI/netI     0.0997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            78363
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        0.862
_diffrn_reflns_theta_max         0.866
_diffrn_reflns_theta_min         0.122
_diffrn_ambient_temperature      79
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_detector                 
;
Falcon 3 direct electron camera (integration mode)
;
_diffrn_detector_type            CMOS
_diffrn_measurement_device_type  'Talos Arctica electron microscope'
_diffrn_measurement_method       
;
continuous rotation electron diffraction (MicroED)
;
_diffrn_radiation_probe          electron
_diffrn_radiation_type           electron
_diffrn_radiation_wavelength     0.02508
_diffrn_source                   'Talos Arctica Field Emission Gun'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2923
_reflns_number_total             4413
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'dials.two_theta_refine (Waterman et al., 2016)'
_computing_data_collection       'SerialEM (Mastronarde, 2005)'
_computing_data_reduction        'dials.scale (Beilsten-Edmands et al., 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       9556(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.643
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2208
_refine_ls_R_factor_gt           0.2041
_refine_ls_restrained_S_all      1.643
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4599
_refine_ls_wR_factor_ref         0.4699
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C6(H6), C17(H17), C5(H5), C3(H3), C16(H16)
2.b X=CH2 refined with riding coordinates:
 N29(H29A,H29B), N25(H25A,H25B), N26(H26A,H26B), N30(H30A,H30B)
2.c Idealised tetrahedral OH refined as rotating group:
 O10(H10), O21(H21), O20(H20), O11(H11), O22(H22), O9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O10 O -0.0693(9) 0.5893(6) 0.3728(2) 0.0498(16) Uani 1 1 d . . . . .
H10 H -0.105999 0.618567 0.395968 0.075 Uiso 1 1 calc R U . . .
N29 N -0.2320(8) 0.9732(6) 0.2828(2) 0.0465(17) Uani 1 1 d . . . . .
H29A H -0.233833 1.052210 0.285956 0.056 Uiso 1 1 calc R U . . .
H29B H -0.339800 0.931796 0.283106 0.056 Uiso 1 1 calc R U . . .
C27 C -0.0663(9) 0.9162(7) 0.2774(3) 0.0440(18) Uani 1 1 d . . . . .
O21 O 0.0816(9) 1.0059(5) 0.12571(19) 0.0406(14) Uani 1 1 d . . . . .
H21 H 0.106510 1.029042 0.100922 0.061 Uiso 1 1 calc R U . . .
O28 O -0.0809(8) 0.7968(7) 0.2729(2) 0.0503(17) Uani 1 1 d . . . . .
O8 O -0.1727(10) 0.5794(10) 0.4523(2) 0.071(2) Uani 1 1 d . . . . .
C14 C 0.0662(9) 0.8326(7) 0.1663(2) 0.0404(18) Uani 1 1 d . . . . .
H14 H 0.031487 0.884185 0.189093 0.049 Uiso 1 1 calc R U . . .
C7 C -0.1837(10) 0.4634(8) 0.4490(2) 0.0439(18) Uani 1 1 d . . . . .
C15 C 0.0780(10) 0.7098(7) 0.1737(2) 0.0435(18) Uani 1 1 d . . . . .
C6 C -0.1610(10) 0.2787(7) 0.4070(2) 0.0415(18) Uani 1 1 d . . . . .
H6 H -0.201516 0.234473 0.431163 0.050 Uiso 1 1 calc R U . . .
C17 C 0.1628(11) 0.6876(8) 0.1001(2) 0.049(2) Uani 1 1 d . . . . .
H17 H 0.204315 0.637621 0.077445 0.059 Uiso 1 1 calc R U . . .
C5 C -0.1239(11) 0.2160(8) 0.3699(2) 0.051(2) Uani 1 1 d . . . . .
H5 H -0.129981 0.130184 0.369078 0.061 Uiso 1 1 calc R U . . .
N25 N 0.5921(9) 0.6755(7) 0.3102(2) 0.0537(19) Uani 1 1 d . . . . .
H25A H 0.699312 0.695750 0.297923 0.064 Uiso 1 1 calc R U . . .
H25B H 0.592700 0.618195 0.329724 0.064 Uiso 1 1 calc R U . . .
C3 C -0.0604(10) 0.4047(7) 0.3353(2) 0.0442(18) Uani 1 1 d . . . . .
H3 H -0.028859 0.448728 0.310468 0.053 Uiso 1 1 calc R U . . .
C4 C -0.0773(10) 0.2825(7) 0.3337(2) 0.0414(18) Uani 1 1 d . . . . .
N26 N 0.2680(10) 0.6909(8) 0.3153(2) 0.063(2) Uani 1 1 d . . . . .
H26A H 0.155196 0.719318 0.306932 0.075 Uiso 1 1 calc R U . . .
H26B H 0.275791 0.633406 0.334726 0.075 Uiso 1 1 calc R U . . .
C18 C 0.1876(10) 0.8643(9) 0.0535(3) 0.047(2) Uani 1 1 d . . . . .
O20 O 0.2462(10) 0.7954(8) 0.0237(2) 0.061(2) Uani 1 1 d . . . . .
H20 H 0.271295 0.837248 0.002213 0.092 Uiso 1 1 calc R U . . .
O19 O 0.1774(10) 0.9778(9) 0.0476(2) 0.061(2) Uani 1 1 d . . . . .
N30 N 0.0934(8) 0.9681(6) 0.2765(2) 0.0470(17) Uani 1 1 d . . . . .
H30A H 0.198374 0.925617 0.272849 0.056 Uiso 1 1 calc R U . . .
H30B H 0.100569 1.047144 0.279509 0.056 Uiso 1 1 calc R U . . .
C2 C -0.0896(9) 0.4653(7) 0.3736(2) 0.0417(18) Uani 1 1 d . . . . .
O11 O -0.0521(10) 0.2186(6) 0.2975(2) 0.0510(16) Uani 1 1 d . . . . .
H11 H -0.026284 0.266074 0.277523 0.076 Uiso 1 1 calc R U . . .
O22 O 0.0502(9) 0.6548(6) 0.2105(2) 0.0497(17) Uani 1 1 d . . . . .
H22 H 0.002624 0.703818 0.227760 0.074 Uiso 1 1 calc R U . . .
C16 C 0.1250(11) 0.6340(7) 0.1390(3) 0.055(2) Uani 1 1 d . . . . .
H16 H 0.130557 0.548709 0.142314 0.066 Uiso 1 1 calc R U . . .
O9 O -0.2312(10) 0.3961(6) 0.4811(2) 0.0529(17) Uani 1 1 d . . . . .
H9 H -0.238517 0.439090 0.503144 0.079 Uiso 1 1 calc R U . . .
C23 C 0.4232(8) 0.7337(7) 0.2990(2) 0.0421(19) Uani 1 1 d . . . . .
O24 O 0.4215(7) 0.8149(7) 0.2714(2) 0.0509(18) Uani 1 1 d . . . . .
C13 C 0.1020(9) 0.8816(7) 0.1283(2) 0.0366(17) Uani 1 1 d . . . . .
C12 C 0.1429(10) 0.8090(7) 0.0927(2) 0.0454(19) Uani 1 1 d . . . . .
C1 C -0.1423(8) 0.3999(7) 0.4105(2) 0.0433(19) 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
O10 H10 0.8400 . ?
O10 C2 1.379(10) . ?
N29 H29A 0.8800 . ?
N29 H29B 0.8800 . ?
N29 C27 1.331(9) . ?
C27 O28 1.331(10) . ?
C27 N30 1.254(9) . ?
O21 H21 0.8400 . ?
O21 C13 1.384(9) . ?
O8 C7 1.290(12) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(11) . ?
C14 C13 1.337(10) . ?
C7 O9 1.302(10) . ?
C7 C1 1.431(10) . ?
C15 O22 1.324(10) . ?
C15 C16 1.418(11) . ?
C6 H6 0.9500 . ?
C6 C5 1.384(10) . ?
C6 C1 1.351(10) . ?
C17 H17 0.9500 . ?
C17 C16 1.387(11) . ?
C17 C12 1.369(11) . ?
C5 H5 0.9500 . ?
C5 C4 1.398(10) . ?
N25 H25A 0.8800 . ?
N25 H25B 0.8800 . ?
N25 C23 1.378(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.357(11) . ?
C3 C2 1.394(10) . ?
C4 O11 1.351(9) . ?
N26 H26A 0.8800 . ?
N26 H26B 0.8800 . ?
N26 C23 1.299(9) . ?
C18 O20 1.280(10) . ?
C18 O19 1.269(11) . ?
C18 C12 1.415(11) . ?
O20 H20 0.8400 . ?
N30 H30A 0.8800 . ?
N30 H30B 0.8800 . ?
C2 C1 1.420(10) . ?
O11 H11 0.8400 . ?
O22 H22 0.8400 . ?
C16 H16 0.9500 . ?
O9 H9 0.8400 . ?
C23 O24 1.245(9) . ?
C13 C12 1.411(10) . ?

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 O10 H10 109.5 . . ?
H29A N29 H29B 120.0 . . ?
C27 N29 H29A 120.0 . . ?
C27 N29 H29B 120.0 . . ?
O28 C27 N29 114.7(6) . . ?
N30 C27 N29 124.1(7) . . ?
N30 C27 O28 121.2(6) . . ?
C13 O21 H21 109.5 . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C13 C14 C15 122.4(7) . . ?
O8 C7 O9 121.5(7) . . ?
O8 C7 C1 122.9(7) . . ?
O9 C7 C1 115.6(7) . . ?
C14 C15 C16 117.9(7) . . ?
O22 C15 C14 126.0(7) . . ?
O22 C15 C16 116.0(7) . . ?
C5 C6 H6 118.5 . . ?
C1 C6 H6 118.5 . . ?
C1 C6 C5 123.0(7) . . ?
C16 C17 H17 118.4 . . ?
C12 C17 H17 118.4 . . ?
C12 C17 C16 123.1(7) . . ?
C6 C5 H5 121.0 . . ?
C6 C5 C4 118.1(7) . . ?
C4 C5 H5 121.0 . . ?
H25A N25 H25B 120.0 . . ?
C23 N25 H25A 120.0 . . ?
C23 N25 H25B 120.0 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.8(7) . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.0(7) . . ?
O11 C4 C5 116.4(7) . . ?
O11 C4 C3 122.6(7) . . ?
H26A N26 H26B 120.0 . . ?
C23 N26 H26A 120.0 . . ?
C23 N26 H26B 120.0 . . ?
O20 C18 C12 117.2(8) . . ?
O19 C18 O20 120.1(8) . . ?
O19 C18 C12 122.6(7) . . ?
C18 O20 H20 109.5 . . ?
C27 N30 H30A 120.0 . . ?
C27 N30 H30B 120.0 . . ?
H30A N30 H30B 120.0 . . ?
O10 C2 C3 116.4(6) . . ?
O10 C2 C1 123.4(6) . . ?
C3 C2 C1 120.2(7) . . ?
C4 O11 H11 109.5 . . ?
C15 O22 H22 109.5 . . ?
C15 C16 H16 120.8 . . ?
C17 C16 C15 118.3(7) . . ?
C17 C16 H16 120.8 . . ?
C7 O9 H9 109.5 . . ?
N26 C23 N25 116.4(7) . . ?
O24 C23 N25 120.3(6) . . ?
O24 C23 N26 123.0(6) . . ?
O21 C13 C12 122.7(6) . . ?
C14 C13 O21 115.7(6) . . ?
C14 C13 C12 121.3(7) . . ?
C17 C12 C18 123.1(7) . . ?
C17 C12 C13 116.5(7) . . ?
C13 C12 C18 119.7(7) . . ?
C6 C1 C7 122.2(7) . . ?
C6 C1 C2 117.8(7) . . ?
C2 C1 C7 119.9(7) . . ?

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
O10 C2 C1 C7 2.2(10) . . . . ?
O10 C2 C1 C6 178.8(6) . . . . ?
O21 C13 C12 C17 178.9(6) . . . . ?
O21 C13 C12 C18 7.6(10) . . . . ?
O8 C7 C1 C6 -177.6(7) . . . . ?
O8 C7 C1 C2 -1.2(11) . . . . ?
C14 C15 C16 C17 2.1(10) . . . . ?
C14 C13 C12 C17 -6.3(10) . . . . ?
C14 C13 C12 C18 -177.5(6) . . . . ?
C15 C14 C13 O21 179.1(6) . . . . ?
C15 C14 C13 C12 3.9(10) . . . . ?
C6 C5 C4 C3 2.9(11) . . . . ?
C6 C5 C4 O11 -176.6(7) . . . . ?
C5 C6 C1 C7 179.2(7) . . . . ?
C5 C6 C1 C2 2.7(10) . . . . ?
C3 C2 C1 C7 -176.1(6) . . . . ?
C3 C2 C1 C6 0.5(9) . . . . ?
C4 C3 C2 O10 179.8(6) . . . . ?
C4 C3 C2 C1 -1.8(10) . . . . ?
O20 C18 C12 C17 1.1(11) . . . . ?
O20 C18 C12 C13 171.7(6) . . . . ?
O19 C18 C12 C17 -176.6(7) . . . . ?
O19 C18 C12 C13 -6.0(11) . . . . ?
C2 C3 C4 C5 0.1(10) . . . . ?
C2 C3 C4 O11 179.5(7) . . . . ?
O22 C15 C16 C17 -177.6(7) . . . . ?
C16 C17 C12 C18 177.8(7) . . . . ?
C16 C17 C12 C13 6.9(11) . . . . ?
O9 C7 C1 C6 3.4(10) . . . . ?
O9 C7 C1 C2 179.8(6) . . . . ?
C13 C14 C15 O22 178.0(7) . . . . ?
C13 C14 C15 C16 -1.7(10) . . . . ?
C12 C17 C16 C15 -5.0(11) . . . . ?
C1 C6 C5 C4 -4.4(11) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.237 0.000 0.500 340.4 27.3 ?
2 -0.973 0.500 0.000 340.4 27.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
