# Supplementary Information (SI) for CrystEngComm.
# 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_EG-2MIE
_database_code_depnum_ccdc_archive 'CCDC 2335740'
loop_
_audit_author_name
_audit_author_address
'ziqi pan'
;Tianjin University
China
;
_audit_update_record             
;
2025-01-20 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_audit_creation_date             2025-01-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        EG-2MIE
_chemical_formula_moiety         'C9 H10 O5, C4 H6 N2'
_chemical_formula_sum            'C13 H16 N2 O5'
_chemical_formula_weight         280.28
_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 0.0181 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'

_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                   8.51680(10)
_cell_length_b                   11.7510(2)
_cell_length_c                   14.3094(3)
_cell_angle_alpha                110.381(2)
_cell_angle_beta                 91.880(2)
_cell_angle_gamma                94.517(2)
_cell_volume                     1335.49(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17180
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.8120
_cell_measurement_theta_min      4.0670
_shelx_estimated_absorpt_T_max   0.853
_shelx_estimated_absorpt_T_min   0.811
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23140
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.042
_diffrn_reflns_theta_min         4.032
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  94.00   0.50    0.50    --    5.00  57.00 150.00  238
  2  ω    -79.00  41.00   0.50    0.50    --  -48.80  57.00  30.00  240
  3  ω   -138.00 -11.00   0.50    0.50    --  -48.80 -30.00-110.06  254
  4  ω    -82.00  41.00   0.50    0.50    --  -48.80  38.00 -90.00  246
  5  ω    -83.00  41.00   0.50    0.50    --  -48.80  72.00  90.00  248
  6  ω   -144.00 -21.00   0.50    0.50    -- -110.00  72.00-150.00  246
  7  ω   -199.00 -80.00   0.50    0.50    -- -110.00 -57.00  30.00  238
  8  ω   -144.00 -21.00   0.50    0.50    -- -110.00  72.00 120.00  246
  9  ω   -144.00 -21.00   0.50    0.50    -- -110.00  72.00 -30.00  246
 10  ω   -144.00 -21.00   0.50    0.50    -- -110.00  72.00-180.00  246
 11  ω   -199.00 -75.00   0.50    0.50    -- -110.00 -36.00 -20.96  248
 12  ω   -199.00 -77.00   0.50    0.50    -- -110.00 -38.00  60.00  244
 13  ω   -144.00 -21.00   0.50    0.50    -- -110.00  72.00   0.00  246
 14  ω   -199.00 -80.00   0.50    0.50    -- -110.00 -50.00-108.10  238
 15  ω   -199.00 -80.00   0.50    0.50    -- -110.00 -49.00-175.79  238
 16  ω   -199.00 -78.00   0.50    0.50    -- -110.00 -65.00  97.74  242
 17  ω   -140.00 -21.00   0.50    0.50    -- -110.00  57.00 -90.00  238
 18  ω   -144.00 -21.00   0.50    0.50    -- -110.00  72.00 -60.00  246
 19  ω   -199.00 -77.00   0.50    0.50    -- -110.00 -38.00 150.00  244
 20  ω   -107.00 -81.00   0.50    0.50    -- -110.00  72.00 -90.00   52
 21  ω    -94.00 -49.00   0.50    0.50    -- -110.00  72.00  30.00   90
 22  ω   -141.00 -22.00   0.50    0.50    -- -110.00  72.00  90.00  238
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5296
_reflns_number_total             5544
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0069(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         5544
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.062
_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)+(0.0755P)²+0.5465P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1312
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H9-H5
 2.15 with sigma of 0.01
 H4-H10
 2.15 with sigma of 0.01
 N2-C2 \\sim N5-C30
 with sigma of 0.02
 N2-C4 \\sim N5-C28
 with sigma of 0.02
 N1-C2 \\sim N6-C30
 with sigma of 0.02
 N1-C3 \\sim N6-C29
 with sigma of 0.02
 C2-C1 \\sim C30-C27
 with sigma of 0.02
 C3-C4 \\sim C29-C28
 with sigma of 0.02
 N2-N1 \\sim N5-N6
 with sigma of 0.04
 N2-C3 \\sim N5-C29
 with sigma of 0.04
 N2-C1 \\sim N5-C27
 with sigma of 0.04
 N1-C4 \\sim N6-C28
 with sigma of 0.04
 N1-C1 \\sim N6-C27
 with sigma of 0.04
 C2-C3 \\sim C30-C29
 with sigma of 0.04
 C2-C4 \\sim C30-C28
 with sigma of 0.04
3. Others
 Sof(N5)=Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=Sof(N6)=Sof(C30)=Sof(C27)=
 Sof(H27A)=Sof(H27B)=Sof(H27C)=1-FVAR(1)
 Sof(N2)=Sof(N1)=Sof(C2)=Sof(C3)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(C1)=Sof(H1A)=
 Sof(H1B)=Sof(H1C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C19(H19A,H19B)
4.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C22(H22), C17(H17), C26(H26), C8(H8A), C7(H7), C3(H3B), C4(H4A),
 C28(H28), C29(H29)
4.c Tetrahedral OH refined with riding coordinates:
 O9(H9)
4.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C5(H5A,H5B,H5C), C1(H1A,H1B,H1C),
 C27(H27A,H27B,H27C)
4.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O9 O 0.56757(11) 0.65831(8) 0.79831(7) 0.0217(2) Uani 1 1 d . . . . .
H9 H 0.5800 0.6275 0.8411 0.033 Uiso 1 1 calc DR U . . .
O4 O 0.48611(11) 0.35694(8) 0.71065(7) 0.0221(2) Uani 1 1 d . . . . .
H4 H 0.4419 0.3455 0.6559 0.033 Uiso 1 1 calc DR U . . .
O5 O 0.77610(13) 0.49519(9) 0.73739(8) 0.0262(2) Uani 1 1 d . . . . .
O10 O 0.27879(13) 0.51992(8) 0.73724(8) 0.0261(2) Uani 1 1 d . . . . .
O6 O 0.03263(11) 1.00833(8) 0.88358(8) 0.0263(2) Uani 1 1 d . . . . .
O1 O 1.02168(12) 0.00791(9) 0.63105(8) 0.0283(2) Uani 1 1 d . . . . .
O7 O -0.12533(12) 0.83289(9) 0.82731(8) 0.0311(2) Uani 1 1 d . . . . .
O3 O 0.47919(12) 0.10418(9) 0.65599(9) 0.0316(3) Uani 1 1 d . . . . .
O8 O 0.57745(12) 0.90899(9) 0.88554(9) 0.0325(3) Uani 1 1 d . . . . .
O2 O 1.18041(12) 0.18206(9) 0.66945(9) 0.0346(3) Uani 1 1 d . . . . .
N4 N 0.66345(14) 0.62520(11) 0.96580(8) 0.0256(3) Uani 1 1 d . . . . .
N3 N 0.65542(15) 0.62166(11) 1.11534(9) 0.0271(3) Uani 1 1 d . . . . .
C15 C 0.43389(15) 0.71168(11) 0.81089(9) 0.0199(3) Uani 1 1 d . . . . .
C16 C 0.28540(16) 0.64396(11) 0.78068(9) 0.0204(3) Uani 1 1 d . . . . .
C13 C 0.29915(16) 0.89652(12) 0.86786(10) 0.0232(3) Uani 1 1 d . . . . .
H13 H 0.3035 0.9810 0.8967 0.028 Uiso 1 1 calc R U . . .
C24 C 0.61951(16) 0.30368(12) 0.69824(9) 0.0207(3) Uani 1 1 d . . . . .
C14 C 0.43662(16) 0.83921(12) 0.85508(10) 0.0230(3) Uani 1 1 d . . . . .
C25 C 0.76861(16) 0.37131(11) 0.71130(9) 0.0207(3) Uani 1 1 d . . . . .
C22 C 0.75672(16) 0.11959(12) 0.65715(10) 0.0237(3) Uani 1 1 d . . . . .
H22 H 0.7529 0.0352 0.6385 0.028 Uiso 1 1 calc R U . . .
C23 C 0.61870(16) 0.17610(12) 0.67067(10) 0.0228(3) Uani 1 1 d . . . . .
C20 C 1.04906(16) 0.12880(12) 0.65777(10) 0.0231(3) Uani 1 1 d . . . . .
N2 N 0.3779(2) 0.29411(16) 0.51770(11) 0.0289(4) Uani 0.816(4) 1 d D . P A 1
C6 C 0.60147(17) 0.67433(12) 1.05375(10) 0.0256(3) Uani 1 1 d . . . . .
C11 C 0.00576(16) 0.88675(12) 0.84853(9) 0.0216(3) Uani 1 1 d . . . . .
C17 C 0.14615(15) 0.69989(12) 0.79429(10) 0.0216(3) Uani 1 1 d . . . . .
H17 H 0.0491 0.6536 0.7751 0.026 Uiso 1 1 calc R U . . .
C21 C 0.90156(16) 0.18914(12) 0.67153(9) 0.0216(3) Uani 1 1 d . . . . .
C26 C 0.90819(16) 0.31593(12) 0.69896(9) 0.0221(3) Uani 1 1 d . . . . .
H26 H 1.0049 0.3625 0.7088 0.026 Uiso 1 1 calc R U . . .
N1 N 0.3526(2) 0.28604(17) 0.36565(12) 0.0299(4) Uani 0.816(4) 1 d D . P A 1
C10 C -0.10286(16) 1.07793(12) 0.89272(10) 0.0248(3) Uani 1 1 d . . . . .
H10A H -0.1729 1.0626 0.9400 0.030 Uiso 1 1 calc R U . . .
H10B H -0.1612 1.0563 0.8286 0.030 Uiso 1 1 calc R U . . .
C8 C 0.75476(18) 0.53649(13) 1.06554(11) 0.0290(3) Uani 1 1 d . . . . .
H8A H 0.8084 0.4870 1.0915 0.035 Uiso 1 1 calc R U . . .
C7 C 0.75933(18) 0.53862(13) 0.97202(10) 0.0281(3) Uani 1 1 d . . . . .
H7 H 0.8165 0.4906 0.9212 0.034 Uiso 1 1 calc R U . . .
C9 C -0.03696(18) 1.20989(13) 0.92926(12) 0.0312(3) Uani 1 1 d . . . . .
H9A H 0.0371 1.2223 0.8838 0.047 Uiso 1 1 calc R U . . .
H9B H 0.0154 1.2309 0.9943 0.047 Uiso 1 1 calc R U . . .
H9C H -0.1214 1.2605 0.9330 0.047 Uiso 1 1 calc R U . . .
C18 C 1.0893(2) -0.19503(13) 0.58017(12) 0.0351(3) Uani 1 1 d . . . . .
H18A H 1.0248 -0.2141 0.5194 0.053 Uiso 1 1 calc R U . . .
H18B H 1.0265 -0.2084 0.6305 0.053 Uiso 1 1 calc R U . . .
H18C H 1.1741 -0.2465 0.5684 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4913(2) 0.77056(15) 1.07908(13) 0.0367(4) Uani 1 1 d . . . . .
H5A H 0.5412 0.8429 1.1297 0.055 Uiso 1 1 calc R U . . .
H5B H 0.3977 0.7426 1.1035 0.055 Uiso 1 1 calc R U . . .
H5C H 0.4635 0.7885 1.0205 0.055 Uiso 1 1 calc R U . . .
C2 C 0.3305(3) 0.3543(2) 0.45970(16) 0.0296(5) Uani 0.816(4) 1 d D . P A 1
C3 C 0.4150(3) 0.18100(17) 0.36377(17) 0.0314(5) Uani 0.816(4) 1 d D . P A 1
H3B H 0.4411 0.1184 0.3075 0.038 Uiso 0.816(4) 1 calc R U P A 1
C4 C 0.4309(2) 0.18616(17) 0.45913(16) 0.0304(4) Uani 0.816(4) 1 d D . P A 1
H4A H 0.4703 0.1277 0.4812 0.036 Uiso 0.816(4) 1 calc R U P A 1
C1 C 0.2648(4) 0.4736(2) 0.4923(2) 0.0488(6) Uani 0.816(4) 1 d D . P A 1
H1A H 0.1636 0.4659 0.5183 0.073 Uiso 0.816(4) 1 calc R U P A 1
H1B H 0.2531 0.5003 0.4364 0.073 Uiso 0.816(4) 1 calc R U P A 1
H1C H 0.3349 0.5323 0.5434 0.073 Uiso 0.816(4) 1 calc R U P A 1
N5 N 0.3045(9) 0.3520(8) 0.3833(5) 0.033(2) Uani 0.184(4) 1 d D . P A 2
C28 C 0.2060(11) 0.4364(8) 0.4353(7) 0.032(2) Uani 0.184(4) 1 d D . P A 2
H28 H 0.1419 0.4802 0.4094 0.039 Uiso 0.184(4) 1 calc R U P A 2
C29 C 0.2208(11) 0.4431(10) 0.5322(7) 0.038(2) Uani 0.184(4) 1 d D . P A 2
H29 H 0.1736 0.4952 0.5863 0.045 Uiso 0.184(4) 1 calc R U P A 2
N6 N 0.3220(9) 0.3554(8) 0.5334(5) 0.034(2) Uani 0.184(4) 1 d D . P A 2
C30 C 0.3731(12) 0.3054(9) 0.4432(8) 0.035(3) Uani 0.184(4) 1 d D . P A 2
C27 C 0.4847(16) 0.2086(9) 0.4161(8) 0.043(3) Uani 0.184(4) 1 d D . P A 2
H27A H 0.4262 0.1299 0.3970 0.065 Uiso 0.184(4) 1 calc R U P A 2
H27B H 0.5561 0.2201 0.4727 0.065 Uiso 0.184(4) 1 calc R U P A 2
H27C H 0.5434 0.2139 0.3614 0.065 Uiso 0.184(4) 1 calc R U P A 2
C12 C 0.15389(15) 0.82696(12) 0.83731(9) 0.0211(3) Uani 1 1 d . . . . .
C19 C 1.15597(17) -0.06343(13) 0.61490(11) 0.0287(3) Uani 1 1 d . . . . .
H19A H 1.2214 -0.0426 0.6764 0.034 Uiso 1 1 calc R U . . .
H19B H 1.2195 -0.0483 0.5646 0.034 Uiso 1 1 calc R U . . .
H3A H 0.621(3) 0.639(2) 1.1756(17) 0.051(6) Uiso 1 1 d . . . . .
H1 H 0.345(3) 0.310(2) 0.3139(19) 0.059(7) Uiso 1 1 d . . . . .
H10 H 0.352(4) 0.5111(19) 0.742(2) 0.088(11) Uiso 1 1 d D . . . .
H5 H 0.701(3) 0.502(2) 0.7308(16) 0.064(9) Uiso 1 1 d D . . . .
H3 H 0.395(3) 0.144(2) 0.6630(17) 0.054(6) Uiso 1 1 d . . . . .
H8 H 0.655(3) 0.868(2) 0.8682(17) 0.053(6) Uiso 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
O9 H9 0.8200 . ?
O9 C15 1.3301(16) . ?
O4 H4 0.8200 . ?
O4 C24 1.3274(16) . ?
O5 C25 1.3668(15) . ?
O5 H5 0.66(2) . ?
O10 C16 1.3667(15) . ?
O10 H10 0.64(3) . ?
O6 C11 1.3369(15) . ?
O6 C10 1.4496(15) . ?
O1 C20 1.3351(16) . ?
O1 C19 1.4484(16) . ?
O7 C11 1.2132(17) . ?
O3 C23 1.3682(16) . ?
O3 H3 0.88(2) . ?
O8 C14 1.3648(16) . ?
O8 H8 0.84(2) . ?
O2 C20 1.2147(17) . ?
N4 C6 1.3348(18) . ?
N4 C7 1.3781(18) . ?
N3 C6 1.3300(18) . ?
N3 C8 1.3790(19) . ?
N3 H3A 0.88(2) . ?
C15 C16 1.4091(18) . ?
C15 C14 1.4071(18) . ?
C16 C17 1.3875(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.3821(19) . ?
C13 C12 1.3950(18) . ?
C24 C25 1.4145(18) . ?
C24 C23 1.4106(18) . ?
C25 C26 1.3869(18) . ?
C22 H22 0.9300 . ?
C22 C23 1.3815(19) . ?
C22 C21 1.3926(19) . ?
C20 C21 1.4761(18) . ?
N2 C2 1.336(3) . ?
N2 C4 1.375(3) . ?
C6 C5 1.482(2) . ?
C11 C12 1.4783(18) . ?
C17 H17 0.9300 . ?
C17 C12 1.3980(18) . ?
C21 C26 1.3982(18) . ?
C26 H26 0.9300 . ?
N1 C2 1.334(3) . ?
N1 C3 1.374(3) . ?
N1 H1 0.89(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.5073(19) . ?
C8 H8A 0.9300 . ?
C8 C7 1.349(2) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 C19 1.506(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C2 C1 1.477(3) . ?
C3 H3B 0.9300 . ?
C3 C4 1.346(3) . ?
C4 H4A 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N5 C28 1.378(10) . ?
N5 C30 1.312(12) . ?
N5 H1 1.03(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.361(10) . ?
C29 H29 0.9300 . ?
C29 N6 1.399(11) . ?
N6 C30 1.322(12) . ?
C30 C27 1.494(11) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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
C15 O9 H9 109.5 . . ?
C24 O4 H4 109.5 . . ?
C25 O5 H5 100(2) . . ?
C16 O10 H10 101(2) . . ?
C11 O6 C10 117.51(10) . . ?
C20 O1 C19 118.14(11) . . ?
C23 O3 H3 114.4(16) . . ?
C14 O8 H8 112.3(17) . . ?
C6 N4 C7 108.70(12) . . ?
C6 N3 C8 109.01(12) . . ?
C6 N3 H3A 120.5(14) . . ?
C8 N3 H3A 130.2(14) . . ?
O9 C15 C16 121.87(11) . . ?
O9 C15 C14 120.57(12) . . ?
C14 C15 C16 117.55(12) . . ?
O10 C16 C15 118.97(11) . . ?
O10 C16 C17 119.31(12) . . ?
C17 C16 C15 121.72(11) . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.64(12) . . ?
C12 C13 H13 120.2 . . ?
O4 C24 C25 121.97(11) . . ?
O4 C24 C23 121.21(12) . . ?
C23 C24 C25 116.82(12) . . ?
O8 C14 C15 119.85(12) . . ?
O8 C14 C13 118.68(12) . . ?
C13 C14 C15 121.47(12) . . ?
O5 C25 C24 119.23(12) . . ?
O5 C25 C26 118.71(12) . . ?
C26 C25 C24 122.06(11) . . ?
C23 C22 H22 120.1 . . ?
C23 C22 C21 119.90(12) . . ?
C21 C22 H22 120.1 . . ?
O3 C23 C24 120.39(12) . . ?
O3 C23 C22 117.88(11) . . ?
C22 C23 C24 121.73(12) . . ?
O1 C20 C21 112.04(11) . . ?
O2 C20 O1 123.53(12) . . ?
O2 C20 C21 124.43(12) . . ?
C2 N2 C4 109.35(18) . . ?
N4 C6 C5 126.29(13) . . ?
N3 C6 N4 108.16(12) . . ?
N3 C6 C5 125.55(13) . . ?
O6 C11 C12 112.05(11) . . ?
O7 C11 O6 123.39(12) . . ?
O7 C11 C12 124.55(12) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C12 119.00(12) . . ?
C12 C17 H17 120.5 . . ?
C22 C21 C20 119.88(12) . . ?
C22 C21 C26 120.39(12) . . ?
C26 C21 C20 119.73(12) . . ?
C25 C26 C21 119.09(12) . . ?
C25 C26 H26 120.5 . . ?
C21 C26 H26 120.5 . . ?
C2 N1 C3 109.66(19) . . ?
C2 N1 H1 124.9(16) . . ?
C3 N1 H1 124.6(16) . . ?
O6 C10 H10A 110.6 . . ?
O6 C10 H10B 110.6 . . ?
O6 C10 C9 105.71(11) . . ?
H10A C10 H10B 108.7 . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
N3 C8 H8A 126.6 . . ?
C7 C8 N3 106.90(12) . . ?
C7 C8 H8A 126.6 . . ?
N4 C7 H7 126.4 . . ?
C8 C7 N4 107.23(12) . . ?
C8 C7 H7 126.4 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C2 C1 127.0(2) . . ?
N1 C2 N2 107.1(2) . . ?
N1 C2 C1 125.9(2) . . ?
N1 C3 H3B 126.6 . . ?
C4 C3 N1 106.79(17) . . ?
C4 C3 H3B 126.6 . . ?
N2 C4 H4A 126.4 . . ?
C3 C4 N2 107.10(17) . . ?
C3 C4 H4A 126.4 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C28 N5 H1 143.5(17) . . ?
C30 N5 C28 110.1(8) . . ?
C30 N5 H1 106.4(17) . . ?
N5 C28 H28 126.7 . . ?
C29 C28 N5 106.6(7) . . ?
C29 C28 H28 126.7 . . ?
C28 C29 H29 127.2 . . ?
C28 C29 N6 105.6(7) . . ?
N6 C29 H29 127.2 . . ?
C30 N6 C29 109.3(8) . . ?
N5 C30 N6 108.2(9) . . ?
N5 C30 C27 127.2(10) . . ?
N6 C30 C27 124.5(9) . . ?
C30 C27 H27A 109.5 . . ?
C30 C27 H27B 109.5 . . ?
C30 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C13 C12 C11 120.44(11) . . ?
C13 C12 C17 120.61(12) . . ?
C17 C12 C11 118.95(12) . . ?
O1 C19 C18 106.19(12) . . ?
O1 C19 H19A 110.5 . . ?
O1 C19 H19B 110.5 . . ?
C18 C19 H19A 110.5 . . ?
C18 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?

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
O9 C15 C16 O10 0.01(18) . . . . ?
O9 C15 C16 C17 179.73(11) . . . . ?
O9 C15 C14 O8 -0.12(19) . . . . ?
O9 C15 C14 C13 179.31(11) . . . . ?
O4 C24 C25 O5 -0.06(18) . . . . ?
O4 C24 C25 C26 179.61(11) . . . . ?
O4 C24 C23 O3 0.05(19) . . . . ?
O4 C24 C23 C22 179.73(12) . . . . ?
O5 C25 C26 C21 -179.51(11) . . . . ?
O10 C16 C17 C12 -178.99(11) . . . . ?
O6 C11 C12 C13 3.85(18) . . . . ?
O6 C11 C12 C17 -175.21(11) . . . . ?
O1 C20 C21 C22 0.43(18) . . . . ?
O1 C20 C21 C26 -179.57(11) . . . . ?
O7 C11 C12 C13 -177.17(13) . . . . ?
O7 C11 C12 C17 3.8(2) . . . . ?
O2 C20 C21 C22 -179.37(13) . . . . ?
O2 C20 C21 C26 0.6(2) . . . . ?
N3 C8 C7 N4 0.23(17) . . . . ?
C15 C16 C17 C12 1.30(19) . . . . ?
C16 C15 C14 O8 -179.92(12) . . . . ?
C16 C15 C14 C13 -0.49(19) . . . . ?
C16 C17 C12 C13 -1.19(19) . . . . ?
C16 C17 C12 C11 177.87(11) . . . . ?
C24 C25 C26 C21 0.82(19) . . . . ?
C14 C15 C16 O10 179.81(11) . . . . ?
C14 C15 C16 C17 -0.47(19) . . . . ?
C14 C13 C12 C11 -178.79(12) . . . . ?
C14 C13 C12 C17 0.3(2) . . . . ?
C25 C24 C23 O3 -179.59(12) . . . . ?
C25 C24 C23 C22 0.09(19) . . . . ?
C22 C21 C26 C25 -0.21(19) . . . . ?
C23 C24 C25 O5 179.58(11) . . . . ?
C23 C24 C25 C26 -0.75(19) . . . . ?
C23 C22 C21 C20 179.57(12) . . . . ?
C23 C22 C21 C26 -0.4(2) . . . . ?
C20 O1 C19 C18 -176.76(12) . . . . ?
C20 C21 C26 C25 179.79(11) . . . . ?
C6 N4 C7 C8 -0.21(17) . . . . ?
C6 N3 C8 C7 -0.16(17) . . . . ?
C11 O6 C10 C9 -177.65(11) . . . . ?
C21 C22 C23 O3 -179.82(12) . . . . ?
C21 C22 C23 C24 0.5(2) . . . . ?
N1 C3 C4 N2 0.1(2) . . . . ?
C10 O6 C11 O7 -2.37(19) . . . . ?
C10 O6 C11 C12 176.62(10) . . . . ?
C8 N3 C6 N4 0.03(16) . . . . ?
C8 N3 C6 C5 179.86(14) . . . . ?
C7 N4 C6 N3 0.11(16) . . . . ?
C7 N4 C6 C5 -179.72(14) . . . . ?
C2 N2 C4 C3 -0.1(2) . . . . ?
C2 N1 C3 C4 0.0(2) . . . . ?
C3 N1 C2 N2 0.0(3) . . . . ?
C3 N1 C2 C1 -179.7(2) . . . . ?
C4 N2 C2 N1 0.0(2) . . . . ?
C4 N2 C2 C1 179.7(2) . . . . ?
N5 C28 C29 N6 -3.6(11) . . . . ?
C28 N5 C30 N6 0.6(11) . . . . ?
C28 N5 C30 C27 178.2(11) . . . . ?
C28 C29 N6 C30 4.2(12) . . . . ?
C29 N6 C30 N5 -3.0(12) . . . . ?
C29 N6 C30 C27 179.4(10) . . . . ?
C30 N5 C28 C29 2.0(11) . . . . ?
C12 C13 C14 O8 -179.97(12) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C19 O1 C20 O2 -0.2(2) . . . . ?
C19 O1 C20 C21 -179.99(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_EG-Hydrate
_database_code_depnum_ccdc_archive 'CCDC 2408322'
loop_
_audit_author_name
_audit_author_address
'Ziqi Pan'
;Tianjin University
China
;
_audit_update_record             
;
2024-12-06 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_audit_creation_date             2024-12-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        EG-Hydrate
_chemical_formula_moiety         'C9 H10 O5, 2.5(H2 O)'
_chemical_formula_sum            'C9 H15 O7.50'
_chemical_formula_weight         243.21
_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 0.0181 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'
O O 0.0492 0.0322 '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                   7.0043(2)
_cell_length_b                   11.7986(3)
_cell_length_c                   14.0615(4)
_cell_angle_alpha                79.478(2)
_cell_angle_beta                 83.701(2)
_cell_angle_gamma                82.920(2)
_cell_volume                     1129.26(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14113
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1580
_cell_measurement_theta_min      3.1860
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.794
_exptl_absorpt_coefficient_mu    1.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19643
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.267
_diffrn_reflns_theta_min         3.209
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  48.00   0.50    0.05    --   59.34 -94.00-180.00   52
  2  ω     24.00  49.00   0.50    0.05    --   59.34 -94.00 -90.00   50
  3  ω   -101.00 -50.00   0.50    0.05    --  -60.24 -15.00 -30.00  102
  4  ω    -96.00 -40.00   0.50    0.05    --  -60.24 -15.00 -90.00  112
  5  ω   -107.00 -53.00   0.50    0.05    --  -60.24 -15.00  30.00  108
  6  ω    -68.00 -42.00   0.50    0.05    --  -60.24 -15.00-180.00   52
  7  ω    -67.00 -42.00   0.50    0.05    --  -60.24 -15.00 150.00   50
  8  ω     37.00  63.00   0.50    0.05    --   72.68 -94.00  30.00   52
  9  ω     66.00  92.00   0.50    0.05    --   72.68-125.00-120.00   52
 10  ω     32.00  57.00   0.50    0.05    --   72.68 -94.00 -30.00   50
 11  ω     33.00  65.00   0.50    0.05    --   72.68 -94.00  90.00   64
 12  ω     28.00  53.00   0.50    0.05    --   72.68-125.00-120.00   50
 13  ω    -96.00 -70.00   0.50    0.05    --  -74.29 125.00-120.00   52
 14  ω   -121.00 -71.00   0.50    0.05    --  -74.29 -15.00  90.00  100
 15  ω    -56.00 -29.00   0.50    0.05    --  -74.29 125.00-120.00   54
 16  ω   -120.00 -85.00   0.50    0.05    --  -78.05 -15.00-150.00   70
 17  ω   -121.00 -80.00   0.50    0.05    --  -78.05 -15.00 150.00   82
 18  ω   -100.00 -72.00   0.50    0.05    --  -78.05 125.00   0.00   56
 19  ω    -96.00 -60.00   0.50    0.05    --  -78.05 -15.00 -30.00   72
 20  ω   -125.00 -91.00   0.50    0.05    --  -78.05 -15.00  60.00   68
 21  ω     90.00 118.00   0.50    0.05    --   79.03  15.00  60.00   56
 22  ω     53.00  99.00   0.50    0.05    --   79.03  15.00-150.00   92
 23  ω     76.00 127.00   0.50    0.05    --   79.03  15.00   0.00  102
 24  ω     41.00  66.00   0.50    0.05    --   79.03-125.00 -60.00   50
 25  ω     76.00 101.00   0.50    0.05    --   79.03-125.00 -60.00   50
 26  ω     37.00  62.00   0.50    0.05    --   79.03-125.00-120.00   50
 27  ω     75.00 101.00   0.50    0.05    --   79.03-125.00-150.00   52
 28  ω     43.00  69.00   0.50    0.05    --   79.03-125.00-150.00   52
 29  ω     74.00  99.00   0.50    0.05    --   79.03  15.00  30.00   50
 30  ω     76.00 101.00   0.50    0.05    --   79.03-125.00-120.00   50
 31  ω     57.00  83.00   0.50    0.05    --   79.03 -94.00-180.00   52
 32  ω    -91.00 -62.00   0.50    0.05    --  -82.00 109.00 -99.63   58
 33  ω    -83.00 -44.00   0.50    0.05    --  -82.00  90.00 125.60   78
 34  ω    -90.00 -37.00   0.50    0.05    --  -82.00 129.00 -53.37  106
 35  ω    -73.00 -48.00   0.50    0.05    --  -82.00 108.00 158.96   50
 36  ω   -130.00-105.00   0.50    0.05    --  -82.00 -41.00-161.98   50
 37  ω    -83.00 -38.00   0.50    0.05    --  -82.00 131.00  12.61   90
 38  ω    -68.00 -43.00   0.50    0.05    --  -82.00  71.00-124.78   50
 39  ω    -97.00 -69.00   0.50    0.05    --  -82.00 114.00   0.07   56
 40  ω    -64.00 -38.00   0.50    0.05    --  -82.00 125.00 -67.17   52
 41  ω    -90.00 -56.00   0.50    0.05    --  -82.00 103.00-139.35   68
 42  ω   -100.00 -74.00   0.50    0.05    --  -82.00 125.00 -67.17   52
 43  ω   -124.00 -98.00   0.50    0.05    --  -82.00 -61.00 174.10   52
 44  ω    -98.00 -37.00   0.50    0.05    --  -82.00 131.00-108.42  122
 45  ω    -81.00 -49.00   0.50    0.05    --  -82.00 125.00  31.24   64
 46  ω    -77.00 -37.00   0.50    0.05    --  -82.00 125.00  -4.40   80
 47  ω    -75.00 -50.00   0.50    0.05    --  -82.00  94.00-105.59   50
 48  ω   -123.00 -97.00   0.50    0.05    --  -82.00 -66.00  33.47   52
 49  ω    -67.00 -38.00   0.50    0.05    --  -82.00 129.00 151.47   58
 50  ω   -124.00 -98.00   0.50    0.05    --  -82.00 -58.00 -78.36   52
 51  ω    -92.00 -40.00   0.50    0.05    --  -82.00 109.00  82.21  104
 52  ω   -127.00 -98.00   0.50    0.05    --  -82.00 -52.00-137.26   58
 53  ω    -64.00 -39.00   0.50    0.05    --  -82.00 130.00 -92.42   50
 54  ω   -131.00-106.00   0.50    0.05    --  -82.00 -36.00 149.85   50
 55  ω    -63.00 -38.00   0.50    0.05    --  -82.00 131.00  50.05   50
 56  ω    -96.00 -50.00   0.50    0.05    --  -82.00 114.00 -18.82   92
 57  ω   -124.00 -98.00   0.50    0.05    --  -82.00 -47.00 -56.82   52
 58  ω   -123.00 -98.00   0.50    0.05    --  -82.00 -36.00 -29.43   50
 59  ω    -64.00 -39.00   0.50    0.05    --  -82.00 111.00 -64.40   50
 60  ω    -95.00 -67.00   0.50    0.05    --  -82.00 118.00 167.57   56
 61  ω   -123.00 -98.00   0.50    0.05    --  -82.00 -55.00 137.49   50
 62  ω    -94.00 -68.00   0.50    0.05    --  -82.00 118.00 108.56   52
 63  ω    -66.00 -36.00   0.50    0.05    --  -82.00 127.00-146.50   60
 64  ω    -97.00 -47.00   0.50    0.05    --  -82.00 114.00  60.40  100
 65  ω    -97.00 -64.00   0.50    0.05    --  -82.00 114.00 -75.14   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1345148000
_diffrn_orient_matrix_UB_12      -0.1110111000
_diffrn_orient_matrix_UB_13      -0.0120020000
_diffrn_orient_matrix_UB_21      0.1636463000
_diffrn_orient_matrix_UB_22      0.0740889000
_diffrn_orient_matrix_UB_23      -0.0459205000
_diffrn_orient_matrix_UB_31      0.0681415000
_diffrn_orient_matrix_UB_32      -0.0048519000
_diffrn_orient_matrix_UB_33      0.1013140000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4202
_reflns_number_total             4504
_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       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0020(3)
_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   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4504
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.058
_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)+(0.0530P)²+0.3569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0919
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O29-H29A = O29-H29B
 0.87 with sigma of 0.02
 O30-H30A = O30-H30B
 0.87 with sigma of 0.02
 O31-H31A = O31-H31B
 0.87 with sigma of 0.02
 O32-H32A = O32-H32B
 0.87 with sigma of 0.02
 O33-H33A = O33-H33B
 0.87 with sigma of 0.02
 H29A-H29B
 1.38 with sigma of 0.04
 H30A-H30B
 1.38 with sigma of 0.04
 H31A-H31B
 1.38 with sigma of 0.04
 H32A-H32B
 1.38 with sigma of 0.04
 H33A-H33B
 1.38 with sigma of 0.04
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C20(H20), C16(H16), C2(H2)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C24(H24A,H24B,H24C)
2.d Idealised tetrahedral OH refined as rotating group:
 O13(H13), O14(H14), O12(H12), O26(H26), O28(H28), O27(H27)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O8 O 0.43433(11) 0.65724(7) 0.26921(6) 0.01674(17) Uani 1 1 d . . . . .
O13 O 0.11255(12) 0.57451(6) 0.60021(6) 0.01760(18) Uani 1 1 d . . . . .
H13 H 0.072985 0.532512 0.651719 0.026 Uiso 1 1 calc R U . . .
O22 O 0.23015(11) 0.37045(7) 0.09847(6) 0.01714(18) Uani 1 1 d . . . . .
O14 O 0.15819(12) 0.34158(7) 0.65631(5) 0.01729(17) Uani 1 1 d . . . . .
H14 H 0.150723 0.270352 0.660091 0.026 Uiso 1 1 calc R U . . .
O25 O 0.07183(13) 0.44584(7) 0.22368(6) 0.02184(19) Uani 1 1 d . . . . .
O12 O 0.36762(12) 0.20112(6) 0.53828(6) 0.01817(18) Uani 1 1 d . . . . .
H12 H 0.365246 0.162473 0.493903 0.027 Uiso 1 1 calc R U . . .
O11 O 0.54188(12) 0.48748(7) 0.22346(6) 0.02097(19) Uani 1 1 d . . . . .
O26 O 0.31515(12) 0.71278(7) -0.17026(6) 0.01879(18) Uani 1 1 d . . . . .
H26 H 0.357772 0.649345 -0.187724 0.028 Uiso 1 1 calc R U . . .
O28 O 0.17609(12) 0.89694(7) -0.09556(6) 0.01896(18) Uani 1 1 d . . . . .
H28 H 0.117698 0.949258 -0.066722 0.028 Uiso 1 1 calc R U . . .
O27 O 0.01936(12) 0.88302(7) 0.09166(6) 0.01915(18) Uani 1 1 d . . . . .
H27 H 0.003102 0.871283 0.152606 0.029 Uiso 1 1 calc R U . . .
C15 C 0.15888(15) 0.57389(9) 0.07773(8) 0.0152(2) Uani 1 1 d . . . . .
C19 C 0.08971(15) 0.78095(9) 0.06025(8) 0.0153(2) Uani 1 1 d . . . . .
C21 C 0.14783(15) 0.45919(9) 0.14110(8) 0.0157(2) Uani 1 1 d . . . . .
C5 C 0.20443(15) 0.50620(9) 0.53708(8) 0.0141(2) Uani 1 1 d . . . . .
C6 C 0.27269(15) 0.55741(9) 0.44520(8) 0.0150(2) Uani 1 1 d . . . . .
H6 H 0.252148 0.639101 0.425816 0.018 Uiso 1 1 calc R U . . .
C23 C 0.21958(17) 0.25635(9) 0.15802(8) 0.0188(2) Uani 1 1 d . . . . .
H23A H 0.083491 0.244072 0.180391 0.023 Uiso 1 1 calc R U . . .
H23B H 0.292356 0.249223 0.215706 0.023 Uiso 1 1 calc R U . . .
C3 C 0.33392(15) 0.31783(9) 0.50140(8) 0.0148(2) Uani 1 1 d . . . . .
C4 C 0.23106(15) 0.38604(9) 0.56546(8) 0.0142(2) Uani 1 1 d . . . . .
C20 C 0.08327(15) 0.67219(9) 0.11734(8) 0.0155(2) Uani 1 1 d . . . . .
H20 H 0.028054 0.664533 0.182695 0.019 Uiso 1 1 calc R U . . .
C7 C 0.45660(15) 0.54152(9) 0.28423(8) 0.0153(2) Uani 1 1 d . . . . .
C9 C 0.53187(16) 0.71404(10) 0.17895(8) 0.0180(2) Uani 1 1 d . . . . .
H9A H 0.474832 0.697663 0.122156 0.022 Uiso 1 1 calc R U . . .
H9B H 0.671080 0.685764 0.174426 0.022 Uiso 1 1 calc R U . . .
C17 C 0.24318(15) 0.69312(9) -0.07514(8) 0.0154(2) Uani 1 1 d . . . . .
C18 C 0.16859(15) 0.79201(9) -0.03606(8) 0.0153(2) Uani 1 1 d . . . . .
C16 C 0.23981(15) 0.58385(9) -0.01861(8) 0.0156(2) Uani 1 1 d . . . . .
H16 H 0.291689 0.516710 -0.044885 0.019 Uiso 1 1 calc R U . . .
C2 C 0.40346(15) 0.36794(9) 0.40926(8) 0.0154(2) Uani 1 1 d . . . . .
H2 H 0.471716 0.321135 0.365720 0.018 Uiso 1 1 calc R U . . .
C10 C 0.50429(18) 0.84211(10) 0.18151(9) 0.0237(3) Uani 1 1 d . . . . .
H10A H 0.570162 0.883736 0.122771 0.036 Uiso 1 1 calc R U . . .
H10B H 0.558679 0.856783 0.238880 0.036 Uiso 1 1 calc R U . . .
H10C H 0.366095 0.869160 0.184563 0.036 Uiso 1 1 calc R U . . .
C1 C 0.37204(15) 0.48833(9) 0.38100(8) 0.0144(2) Uani 1 1 d . . . . .
C24 C 0.30651(18) 0.16807(10) 0.09598(9) 0.0229(3) Uani 1 1 d . . . . .
H24A H 0.236855 0.178233 0.037744 0.034 Uiso 1 1 calc R U . . .
H24B H 0.296350 0.089861 0.133025 0.034 Uiso 1 1 calc R U . . .
H24C H 0.442791 0.178774 0.076869 0.034 Uiso 1 1 calc R U . . .
O29 O 0.04074(12) 0.12551(7) 0.71501(6) 0.01951(18) Uani 1 1 d D . . . .
H29A H 0.115(2) 0.0631(12) 0.7033(11) 0.029 Uiso 1 1 d D U . . .
H29B H -0.055(2) 0.1257(14) 0.6818(11) 0.029 Uiso 1 1 d D U . . .
O30 O 0.04143(13) 0.80861(7) 0.59555(6) 0.02201(19) Uani 1 1 d D . . . .
H30A H 0.057(2) 0.7322(12) 0.6008(12) 0.033 Uiso 1 1 d D U . . .
H30B H -0.081(2) 0.8267(14) 0.6073(12) 0.033 Uiso 1 1 d D U . . .
O31 O 0.23878(12) 0.87118(7) 0.41615(6) 0.02058(18) Uani 1 1 d D . . . .
H31A H 0.172(2) 0.8532(14) 0.4718(10) 0.031 Uiso 1 1 d D U . . .
H31B H 0.354(2) 0.8367(14) 0.4223(12) 0.031 Uiso 1 1 d D U . . .
O32 O 0.26963(12) 0.92103(7) 0.69095(6) 0.02151(18) Uani 1 1 d D . . . .
H32A H 0.200(2) 0.8843(14) 0.6604(11) 0.032 Uiso 1 1 d D U . . .
H32B H 0.270(2) 0.8824(14) 0.7492(10) 0.032 Uiso 1 1 d D U . . .
O33 O 0.35190(13) 0.09038(7) 0.39072(6) 0.02128(19) Uani 1 1 d D . . . .
H33A H 0.319(2) 0.0204(12) 0.4008(12) 0.032 Uiso 1 1 d D U . . .
H33B H 0.469(2) 0.0848(14) 0.3612(12) 0.032 Uiso 1 1 d D 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
O8 C7 1.3351(13) . ?
O8 C9 1.4624(13) . ?
O13 H13 0.8400 . ?
O13 C5 1.3638(12) . ?
O22 C21 1.3389(13) . ?
O22 C23 1.4555(13) . ?
O14 H14 0.8400 . ?
O14 C4 1.3586(13) . ?
O25 C21 1.2144(14) . ?
O12 H12 0.8400 . ?
O12 C3 1.3808(13) . ?
O11 C7 1.2193(13) . ?
O26 H26 0.8400 . ?
O26 C17 1.3655(13) . ?
O28 H28 0.8400 . ?
O28 C18 1.3651(13) . ?
O27 H27 0.8400 . ?
O27 C19 1.3743(13) . ?
C15 C21 1.4838(15) . ?
C15 C20 1.3984(15) . ?
C15 C16 1.3999(15) . ?
C19 C20 1.3868(15) . ?
C19 C18 1.3947(15) . ?
C5 C6 1.3833(15) . ?
C5 C4 1.3958(15) . ?
C6 H6 0.9500 . ?
C6 C1 1.3981(14) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5085(16) . ?
C3 C4 1.3992(15) . ?
C3 C2 1.3850(15) . ?
C20 H20 0.9500 . ?
C7 C1 1.4828(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5061(16) . ?
C17 C18 1.3990(15) . ?
C17 C16 1.3869(15) . ?
C16 H16 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.4000(15) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O29 H29A 0.879(13) . ?
O29 H29B 0.855(13) . ?
O30 H30A 0.885(13) . ?
O30 H30B 0.865(14) . ?
O31 H31A 0.873(13) . ?
O31 H31B 0.865(13) . ?
O32 H32A 0.883(13) . ?
O32 H32B 0.862(13) . ?
O33 H33A 0.868(13) . ?
O33 H33B 0.878(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O8 C9 115.55(8) . . ?
C5 O13 H13 109.5 . . ?
C21 O22 C23 115.02(8) . . ?
C4 O14 H14 109.5 . . ?
C3 O12 H12 109.5 . . ?
C17 O26 H26 109.5 . . ?
C18 O28 H28 109.5 . . ?
C19 O27 H27 109.5 . . ?
C20 C15 C21 117.57(10) . . ?
C20 C15 C16 120.95(10) . . ?
C16 C15 C21 121.48(10) . . ?
O27 C19 C20 124.15(10) . . ?
O27 C19 C18 115.54(9) . . ?
C20 C19 C18 120.30(10) . . ?
O22 C21 C15 113.47(9) . . ?
O25 C21 O22 122.63(10) . . ?
O25 C21 C15 123.90(10) . . ?
O13 C5 C6 119.28(9) . . ?
O13 C5 C4 120.23(9) . . ?
C6 C5 C4 120.49(10) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C1 119.67(10) . . ?
C1 C6 H6 120.2 . . ?
O22 C23 H23A 110.3 . . ?
O22 C23 H23B 110.3 . . ?
O22 C23 C24 107.31(9) . . ?
H23A C23 H23B 108.5 . . ?
C24 C23 H23A 110.3 . . ?
C24 C23 H23B 110.3 . . ?
O12 C3 C4 115.56(9) . . ?
O12 C3 C2 123.68(9) . . ?
C2 C3 C4 120.69(10) . . ?
O14 C4 C5 117.32(9) . . ?
O14 C4 C3 123.24(9) . . ?
C5 C4 C3 119.41(10) . . ?
C15 C20 H20 120.3 . . ?
C19 C20 C15 119.32(10) . . ?
C19 C20 H20 120.3 . . ?
O8 C7 C1 113.38(9) . . ?
O11 C7 O8 121.81(10) . . ?
O11 C7 C1 124.80(10) . . ?
O8 C9 H9A 110.4 . . ?
O8 C9 H9B 110.4 . . ?
O8 C9 C10 106.62(9) . . ?
H9A C9 H9B 108.6 . . ?
C10 C9 H9A 110.4 . . ?
C10 C9 H9B 110.4 . . ?
O26 C17 C18 115.58(9) . . ?
O26 C17 C16 124.00(9) . . ?
C16 C17 C18 120.42(10) . . ?
O28 C18 C19 122.54(9) . . ?
O28 C18 C17 117.51(9) . . ?
C19 C18 C17 119.94(10) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.06(10) . . ?
C17 C16 H16 120.5 . . ?
C3 C2 H2 120.4 . . ?
C3 C2 C1 119.26(10) . . ?
C1 C2 H2 120.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C1 C7 120.75(10) . . ?
C6 C1 C2 120.44(10) . . ?
C2 C1 C7 118.70(9) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H29A O29 H29B 102.7(14) . . ?
H30A O30 H30B 105.5(15) . . ?
H31A O31 H31B 107.0(14) . . ?
H32A O32 H32B 105.4(15) . . ?
H33A O33 H33B 104.7(14) . . ?

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
O8 C7 C1 C6 2.74(14) . . . . ?
O8 C7 C1 C2 -173.48(9) . . . . ?
O13 C5 C6 C1 178.13(10) . . . . ?
O13 C5 C4 O14 1.53(15) . . . . ?
O13 C5 C4 C3 -176.89(9) . . . . ?
O12 C3 C4 O14 -3.63(15) . . . . ?
O12 C3 C4 C5 174.69(9) . . . . ?
O12 C3 C2 C1 -175.82(10) . . . . ?
O11 C7 C1 C6 -178.51(11) . . . . ?
O11 C7 C1 C2 5.27(17) . . . . ?
O26 C17 C18 O28 -0.47(15) . . . . ?
O26 C17 C18 C19 179.28(10) . . . . ?
O26 C17 C16 C15 -178.74(10) . . . . ?
O27 C19 C20 C15 179.83(10) . . . . ?
O27 C19 C18 O28 0.06(15) . . . . ?
O27 C19 C18 C17 -179.67(10) . . . . ?
C21 O22 C23 C24 176.14(9) . . . . ?
C21 C15 C20 C19 -179.59(10) . . . . ?
C21 C15 C16 C17 178.82(10) . . . . ?
C5 C6 C1 C7 -176.41(10) . . . . ?
C5 C6 C1 C2 -0.26(16) . . . . ?
C6 C5 C4 O14 -179.20(9) . . . . ?
C6 C5 C4 C3 2.38(16) . . . . ?
C23 O22 C21 O25 0.80(15) . . . . ?
C23 O22 C21 C15 -179.14(9) . . . . ?
C3 C2 C1 C6 0.41(16) . . . . ?
C3 C2 C1 C7 176.63(10) . . . . ?
C4 C5 C6 C1 -1.14(16) . . . . ?
C4 C3 C2 C1 0.85(16) . . . . ?
C20 C15 C21 O22 -177.58(9) . . . . ?
C20 C15 C21 O25 2.48(17) . . . . ?
C20 C15 C16 C17 -0.43(16) . . . . ?
C20 C19 C18 O28 179.16(10) . . . . ?
C20 C19 C18 C17 -0.57(16) . . . . ?
C7 O8 C9 C10 -174.58(9) . . . . ?
C9 O8 C7 O11 -4.71(15) . . . . ?
C9 O8 C7 C1 174.09(9) . . . . ?
C18 C19 C20 C15 0.81(16) . . . . ?
C18 C17 C16 C15 0.68(16) . . . . ?
C16 C15 C21 O22 3.15(15) . . . . ?
C16 C15 C21 O25 -176.79(11) . . . . ?
C16 C15 C20 C19 -0.32(16) . . . . ?
C16 C17 C18 O28 -179.93(9) . . . . ?
C16 C17 C18 C19 -0.19(16) . . . . ?
C2 C3 C4 O14 179.45(10) . . . . ?
C2 C3 C4 C5 -2.23(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.666
