# Supplementary Information (SI) for Chemical Science.
# 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_rp-463
_database_code_depnum_ccdc_archive 'CCDC 2483227'
loop_
_audit_author_name
_audit_author_address
'Darina Ildarovna Nasyrova'
;N D Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-08-27 deposited with the CCDC.	2025-10-10 downloaded from the CCDC.
;
_audit_creation_date             2024-04-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 O5'
_chemical_formula_sum            'C14 H20 O5'
_chemical_formula_weight         268.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H20O5
_chemical_oxdiff_usercomment     RP-463
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.53370(10)
_cell_length_b                   11.12850(10)
_cell_length_c                   28.2876(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.0310(10)
_cell_angle_gamma                90
_cell_volume                     2666.20(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    22373
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      79.4720
_cell_measurement_theta_min      3.1560
_shelx_estimated_absorpt_T_max   0.878
_shelx_estimated_absorpt_T_min   0.709
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.203
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.117a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -2 17 0.0864
0 3 -16 0.0893
2 4 -14 0.1355
-4 -4 -4 0.1840
-3 -1 -12 0.1351
3 -4 11 0.1415
0 5 -13 0.1156
-5 -3 4 0.1809
-3 3 -10 0.1784
4 4 -8 0.1965
4 -4 7 0.1535
-4 4 -7 0.1926
1 6 -11 0.1200
5 -2 -3 0.1994
4 -5 3 0.1719
-5 -3 9 0.1716
-4 4 -2 0.2102
1 7 -2 0.1606
-3 3 13 0.1935
-4 -2 14 0.1496
4 -2 -14 0.1462
2 -6 -7 0.2010
-1 -6 -8 0.1963
0 -5 -14 0.1617
1 6 9 0.1430
-2 1 18 0.1152
0 -1 -18 0.0773
-2 -4 -12 0.1502
1 3 16 0.1029
0 1 18 0.0854
-2 -1 -16 0.1059
2 1 16 0.0899
2 2 -17 0.0959
-1 0 18 0.0828

_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.16
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.7074 -2.3257 16.8071 -0.1784 -0.7550 -0.6310
0.2386 3.2014 -16.4124 0.1426 0.6074 0.7815
1.9816 4.4408 -13.6127 0.0578 0.2547 0.9653
-4.4099 -3.6190 -4.4066 0.1901 0.7880 -0.5856
-3.4956 -1.2694 -12.3532 0.2321 0.9705 -0.0653
3.1578 -3.6322 10.5614 0.2971 -0.8813 -0.3675
0.4736 5.2220 -12.6861 -0.1517 0.4432 0.8835
-5.0562 -2.8012 4.4126 -0.1825 0.5514 -0.8141
-3.4191 3.3970 -10.1097 -0.3035 0.9007 0.3108
4.1196 4.1031 -8.1008 0.0867 -0.2676 0.9596
3.7904 -4.1016 6.8042 0.4929 -0.8331 -0.2511
-3.8052 4.0871 -6.7707 -0.4933 0.8339 0.2476
0.8128 5.6452 -11.3805 -0.2080 0.3466 0.9147
5.3580 -1.7623 -3.4733 0.6454 -0.6570 0.3897
3.7886 -4.9504 3.0255 0.6845 -0.6940 -0.2232
-4.6510 -2.6473 9.1961 -0.3030 0.3115 -0.9007
-4.2480 4.4297 -1.7336 -0.6984 0.7087 0.0993
0.5730 7.1587 -1.7811 -0.6456 0.0252 0.7632
-3.4803 3.3769 12.7407 -0.9386 0.0409 -0.3425
-3.8310 -1.9192 13.7930 -0.4486 0.0217 -0.8935
3.7193 -2.4085 -13.5663 0.8786 -0.0388 0.4760
1.7747 -6.4201 -6.6895 0.9659 -0.0404 -0.2558
-1.2520 -6.1471 -8.1312 0.7697 0.4560 -0.4467
-0.0279 -4.6367 -13.9593 0.8604 0.5082 -0.0378
1.0820 5.9902 9.1023 -0.7922 -0.4691 0.3903
-1.9024 0.5186 17.8334 -0.6780 -0.3983 -0.6178
0.1392 -0.5620 -18.2162 0.5718 0.6690 0.4749
-2.0596 -4.2228 -12.3058 0.6324 0.7431 -0.2187
1.1932 2.8327 15.8119 -0.6465 -0.7583 -0.0830
0.2624 1.2606 17.8141 -0.6047 -0.7081 -0.3646
-2.1389 -1.0054 -15.7494 0.3923 0.9039 0.1705
1.8882 0.6350 16.2902 -0.3866 -0.8901 -0.2414
1.9797 1.8744 -17.1506 0.4189 0.3748 0.8271
-1.0797 0.2168 18.3005 -0.6034 -0.5374 -0.5891

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            35256
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.826
_diffrn_reflns_theta_min         3.148
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -32.00   0.50    0.30    --  -48.17 -64.00 -71.00  174
  2  ω    -64.00  24.00   0.50    0.30    --  -48.17  64.00  64.00  176
  3  ω    -23.00  65.00   0.50    0.30    --   48.17 -64.00 -71.00  176
  4  ω   -161.00 -73.00   0.50    1.50    --  -90.00 -64.00 -71.00  176
  5  ω    -76.00 -18.00   0.50    1.50    --  -90.00  64.00  64.00  116
  6  ω    135.00 178.00   0.50    1.50    --  111.50  64.00  64.00   86
  7  ω     97.00 130.00   0.50    1.50    --  111.50  64.00  64.00   66
  8  ω     41.00  67.00   0.50    1.50    --  111.50 -64.00 -71.00   52
  9  ω    -84.00 -13.00   0.50    0.30    --  -48.17 125.00-180.00  142
 10  ω     52.00  77.00   0.50    0.30    --   48.17  64.00  64.00   50
 11  ω    -49.00 -22.00   0.50    1.50    --  -90.00  45.00-120.00   54
 12  ω    -47.00 -22.00   0.50    1.50    --  -90.00  45.00 -90.00   50
 13  ω     58.00 104.00   0.50    1.50    --  111.50 -77.00  90.00   92
 14  ω     40.00  70.00   0.50    1.50    --  111.50 -61.00-150.00   60
 15  ω     41.00  71.00   0.50    1.50    --  111.50 -61.00 150.00   60
 16  ω    102.00 146.00   0.50    1.50    --  111.50  15.00-180.00   88
 17  ω    152.00 177.00   0.50    1.50    --  111.50  30.00   0.00   50
 18  ω     79.00 105.00   0.50    1.50    --  111.50 -77.00  30.00   52
 19  ω    150.00 175.00   0.50    1.50    --  111.50  45.00 -90.00   50
 20  ω     74.00 103.00   0.50    1.50    --  111.50 -77.00 -30.00   58
 21  ω     59.00  85.00   0.50    1.50    --  111.50 -77.00-150.00   52
 22  ω    127.00 177.00   0.50    1.50    --  111.50  30.00  30.00  100
 23  ω     41.00 102.00   0.50    1.50    --  111.50 -77.00-180.00  122
 24  ω    108.00 151.00   0.50    1.50    --  111.50  61.00  90.00   86
 25  ω     40.00  70.00   0.50    1.50    --  111.50 -61.00  90.00   60
 26  ω    105.00 177.00   0.50    1.50    --  111.50  45.00 -30.00  144
 27  ω    101.00 156.00   0.50    1.50    --  111.50  30.00-150.00  110
 28  ω     40.00  88.00   0.50    1.50    --  111.50 -95.00   0.00   96
 29  ω     44.00  70.00   0.50    1.50    --  111.50 -61.00 -60.00   52
 30  ω    101.00 132.00   0.50    1.50    --  111.50  45.00 -90.00   62
 31  ω    138.00 165.00   0.50    1.50    --  111.50  77.00  30.00   54
 32  ω    102.00 147.00   0.50    1.50    --  111.50  15.00  30.00   90
 33  ω     41.00  67.00   0.50    1.50    --  111.50 -77.00   0.00   52
 34  ω     71.00 101.00   0.50    1.50    --  111.50 -77.00   0.00   60
 35  ω    106.00 172.00   0.50    1.50    --  111.50  45.00 -60.00  132
 36  ω    108.00 140.00   0.50    1.50    --  111.50  30.00  60.00   64
 37  ω    143.00 174.00   0.50    1.50    --  111.50  30.00  60.00   62
 38  ω     96.00 123.00   0.50    1.50    --  111.50  77.00  30.00   54
 39  ω     41.00  70.00   0.50    1.50    --  111.50 -61.00-120.00   58
 40  ω     40.00  65.00   0.50    1.50    --  111.50 -61.00   0.00   50
 41  ω    124.00 175.00   0.50    1.50    --  111.50  45.00-150.00  102
 42  ω    102.00 143.00   0.50    1.50    --  111.50  45.00  30.00   82
 43  ω    134.00 160.00   0.50    1.50    --  111.50  30.00-180.00   52
 44  ω     53.00  78.00   0.50    1.50    --  111.50   0.00-180.00   50
 45  ω     92.00 118.00   0.50    1.50    --  111.50   0.00-180.00   52
 46  ω     50.00  88.00   0.50    1.50    --  111.50 -95.00-120.00   76
 47  ω     56.00  82.00   0.50    1.50    --  111.50 -95.00  90.00   52
 48  ω     53.00  79.00   0.50    1.50    --  111.50-125.00  30.00   52
 49  ω     85.00 111.00   0.50    1.50    --  111.50-125.00  30.00   52
 50  ω    126.00 152.00   0.50    1.50    --  111.50 125.00 -30.00   52
 51  ω    122.00 164.00   0.50    1.50    --  111.50 125.00  90.00   84
 52  ω     46.00  82.00   0.50    1.50    --  111.50-102.00-133.82   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0687524000
_diffrn_orient_matrix_UB_12      -0.1025799000
_diffrn_orient_matrix_UB_13      -0.0277010000
_diffrn_orient_matrix_UB_21      -0.1453799000
_diffrn_orient_matrix_UB_22      0.0057051000
_diffrn_orient_matrix_UB_23      -0.0380112000
_diffrn_orient_matrix_UB_31      0.0849174000
_diffrn_orient_matrix_UB_32      0.0927847000
_diffrn_orient_matrix_UB_33      -0.0282811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5337
_reflns_number_total             5748
_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 1.171.43.117a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.117a 64-bit (release 26-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.117a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5748
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.048
_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)+(0.0487P)²+1.9139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1116
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C5(H5), C15(H15), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C16(H16A,H16B), C17(H17A,H17B),
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.59427(12) 0.51091(10) 0.69983(3) 0.0215(2) Uani 1 1 d . . . . .
H1 H 0.624(2) 0.582(2) 0.6930(7) 0.037(5) Uiso 1 1 d . . . . .
O2 O 0.62760(10) 0.52757(9) 0.77976(3) 0.0157(2) Uani 1 1 d . . . . .
O3 O 0.75234(10) 0.51750(8) 0.82027(3) 0.01507(19) Uani 1 1 d . . . . .
O4 O 0.57872(10) 0.47297(8) 0.87674(3) 0.01473(19) Uani 1 1 d . . . . .
O5 O 0.64460(10) 0.55839(8) 0.91414(3) 0.01527(19) Uani 1 1 d . . . . .
O6 O 0.90490(12) 0.74302(10) 0.80366(3) 0.0221(2) Uani 1 1 d . . . . .
H6 H 0.873(3) 0.669(2) 0.8109(8) 0.044(6) Uiso 1 1 d . . . . .
O7 O 0.87127(10) 0.72610(8) 0.72353(3) 0.01552(19) Uani 1 1 d . . . . .
O8 O 0.74538(10) 0.73737(8) 0.68337(3) 0.01481(19) Uani 1 1 d . . . . .
O9 O 0.91329(10) 0.77854(8) 0.62493(3) 0.01465(19) Uani 1 1 d . . . . .
O10 O 0.83797(11) 0.69903(8) 0.58679(3) 0.01580(19) Uani 1 1 d . . . . .
C1 C 0.69022(15) 0.46881(12) 0.73980(4) 0.0165(3) Uani 1 1 d . . . . .
H1A H 0.802556 0.492767 0.738514 0.020 Uiso 1 1 calc R U . . .
C2 C 0.67545(16) 0.33407(13) 0.74173(5) 0.0183(3) Uani 1 1 d . . . . .
H2A H 0.733407 0.299309 0.716724 0.022 Uiso 1 1 calc R U . . .
H2B H 0.562684 0.312895 0.733618 0.022 Uiso 1 1 calc R U . . .
C3 C 0.73569(15) 0.27400(12) 0.78913(5) 0.0171(3) Uani 1 1 d . . . . .
H3A H 0.849310 0.292605 0.797061 0.020 Uiso 1 1 calc R U . . .
H3B H 0.725386 0.185819 0.785324 0.020 Uiso 1 1 calc R U . . .
C4 C 0.64834(15) 0.31332(11) 0.83068(5) 0.0154(2) Uani 1 1 d . . . . .
H4A H 0.534381 0.320095 0.819159 0.018 Uiso 1 1 calc R U . . .
H4B H 0.660708 0.250007 0.855442 0.018 Uiso 1 1 calc R U . . .
C5 C 0.70477(14) 0.43197(11) 0.85326(4) 0.0144(2) Uani 1 1 d . . . . .
H5 H 0.796926 0.415454 0.877785 0.017 Uiso 1 1 calc R U . . .
C6 C 0.54396(15) 0.66326(11) 0.91152(4) 0.0150(3) Uani 1 1 d . . . . .
C7 C 0.37655(15) 0.63008(12) 0.92069(4) 0.0145(2) Uani 1 1 d . . . . .
C8 C 0.34816(15) 0.52539(12) 0.94544(4) 0.0159(3) Uani 1 1 d . . . . .
H8 H 0.433023 0.472295 0.955344 0.019 Uiso 1 1 calc R U . . .
C9 C 0.19679(16) 0.49786(13) 0.95577(5) 0.0186(3) Uani 1 1 d . . . . .
H9 H 0.179204 0.426068 0.972511 0.022 Uiso 1 1 calc R U . . .
C10 C 0.07133(16) 0.57473(13) 0.94176(5) 0.0194(3) Uani 1 1 d . . . . .
H10 H -0.031789 0.556000 0.948919 0.023 Uiso 1 1 calc R U . . .
C11 C 0.09829(16) 0.67895(13) 0.91724(5) 0.0205(3) Uani 1 1 d . . . . .
H11 H 0.013100 0.731942 0.907557 0.025 Uiso 1 1 calc R U . . .
C12 C 0.24943(16) 0.70671(12) 0.90666(5) 0.0182(3) Uani 1 1 d . . . . .
H12 H 0.266261 0.778388 0.889743 0.022 Uiso 1 1 calc R U . . .
C13 C 0.55142(17) 0.72807(12) 0.86438(5) 0.0185(3) Uani 1 1 d . . . . .
H13A H 0.494900 0.804695 0.864588 0.028 Uiso 1 1 calc R U . . .
H13B H 0.502222 0.678033 0.838160 0.028 Uiso 1 1 calc R U . . .
H13C H 0.661935 0.743175 0.860094 0.028 Uiso 1 1 calc R U . . .
C14 C 0.62314(16) 0.73794(12) 0.95335(5) 0.0185(3) Uani 1 1 d . . . . .
H14A H 0.566365 0.814048 0.955093 0.028 Uiso 1 1 calc R U . . .
H14B H 0.732967 0.754298 0.948603 0.028 Uiso 1 1 calc R U . . .
H14C H 0.620684 0.693192 0.983090 0.028 Uiso 1 1 calc R U . . .
C15 C 0.81040(15) 0.78578(12) 0.76355(4) 0.0169(3) Uani 1 1 d . . . . .
H15 H 0.697410 0.763649 0.764815 0.020 Uiso 1 1 calc R U . . .
C16 C 0.82886(16) 0.92054(12) 0.76156(5) 0.0184(3) Uani 1 1 d . . . . .
H16A H 0.942309 0.940024 0.769262 0.022 Uiso 1 1 calc R U . . .
H16B H 0.772815 0.956520 0.786747 0.022 Uiso 1 1 calc R U . . .
C17 C 0.76833(16) 0.98059(12) 0.71413(5) 0.0171(3) Uani 1 1 d . . . . .
H17A H 0.654308 0.963048 0.706499 0.021 Uiso 1 1 calc R U . . .
H17B H 0.780228 1.068721 0.717764 0.021 Uiso 1 1 calc R U . . .
C18 C 0.85386(15) 0.93969(12) 0.67247(4) 0.0151(2) Uani 1 1 d . . . . .
H18A H 0.843379 1.003135 0.647757 0.018 Uiso 1 1 calc R U . . .
H18B H 0.967630 0.930545 0.683855 0.018 Uiso 1 1 calc R U . . .
C19 C 0.79253(15) 0.82213(11) 0.64998(4) 0.0143(2) Uani 1 1 d . . . . .
H19 H 0.698640 0.840548 0.626334 0.017 Uiso 1 1 calc R U . . .
C20 C 0.92965(15) 0.58894(12) 0.58720(4) 0.0154(3) Uani 1 1 d . . . . .
C21 C 1.09877(15) 0.61610(12) 0.57818(4) 0.0146(2) Uani 1 1 d . . . . .
C22 C 1.13025(16) 0.71463(12) 0.55010(5) 0.0175(3) Uani 1 1 d . . . . .
H22 H 1.046470 0.766499 0.537929 0.021 Uiso 1 1 calc R U . . .
C23 C 1.28251(17) 0.73760(13) 0.53978(5) 0.0198(3) Uani 1 1 d . . . . .
H23 H 1.301929 0.804856 0.520645 0.024 Uiso 1 1 calc R U . . .
C24 C 1.40655(16) 0.66269(13) 0.55730(5) 0.0200(3) Uani 1 1 d . . . . .
H24 H 1.510625 0.678505 0.550272 0.024 Uiso 1 1 calc R U . . .
C25 C 1.37685(16) 0.56460(13) 0.58515(5) 0.0199(3) Uani 1 1 d . . . . .
H25 H 1.460983 0.512934 0.597207 0.024 Uiso 1 1 calc R U . . .
C26 C 1.22425(16) 0.54150(12) 0.59553(5) 0.0180(3) Uani 1 1 d . . . . .
H26 H 1.205376 0.474109 0.614658 0.022 Uiso 1 1 calc R U . . .
C27 C 0.91798(16) 0.52089(12) 0.63330(5) 0.0188(3) Uani 1 1 d . . . . .
H27A H 0.967496 0.441777 0.631692 0.028 Uiso 1 1 calc R U . . .
H27B H 0.806644 0.510790 0.637753 0.028 Uiso 1 1 calc R U . . .
H27C H 0.972270 0.566267 0.660152 0.028 Uiso 1 1 calc R U . . .
C28 C 0.84212(16) 0.52271(13) 0.54438(5) 0.0200(3) Uani 1 1 d . . . . .
H28A H 0.892690 0.444815 0.540591 0.030 Uiso 1 1 calc R U . . .
H28B H 0.845760 0.570859 0.515527 0.030 Uiso 1 1 calc R U . . .
H28C H 0.731913 0.510080 0.549624 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.86(2) . ?
O1 C1 1.3934(16) . ?
O2 O3 1.4699(12) . ?
O2 C1 1.4625(15) . ?
O3 C5 1.4262(15) . ?
O4 O5 1.4811(12) . ?
O4 C5 1.4076(15) . ?
O5 C6 1.4454(15) . ?
O6 H6 0.90(2) . ?
O6 C15 1.3928(16) . ?
O7 O8 1.4703(12) . ?
O7 C15 1.4617(15) . ?
O8 C19 1.4273(15) . ?
O9 O10 1.4799(12) . ?
O9 C19 1.4064(15) . ?
O10 C20 1.4530(15) . ?
C1 H1A 1.0000 . ?
C1 C2 1.5063(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5300(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5305(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5193(18) . ?
C5 H5 1.0000 . ?
C6 C7 1.5282(18) . ?
C6 C13 1.5241(17) . ?
C6 C14 1.5336(17) . ?
C7 C8 1.3956(18) . ?
C7 C12 1.3986(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3930(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.390(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.3940(19) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15 1.0000 . ?
C15 C16 1.5097(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5310(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5295(17) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5195(18) . ?
C19 H19 1.0000 . ?
C20 C21 1.5262(17) . ?
C20 C27 1.5218(18) . ?
C20 C28 1.5320(18) . ?
C21 C22 1.3992(18) . ?
C21 C26 1.3957(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3899(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.390(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.388(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.3935(19) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.3(14) . . ?
C1 O2 O3 105.68(8) . . ?
C5 O3 O2 108.90(8) . . ?
C5 O4 O5 107.46(9) . . ?
C6 O5 O4 108.07(8) . . ?
C15 O6 H6 109.5(14) . . ?
C15 O7 O8 105.33(8) . . ?
C19 O8 O7 109.22(8) . . ?
C19 O9 O10 107.08(8) . . ?
C20 O10 O9 108.24(8) . . ?
O1 C1 O2 104.05(10) . . ?
O1 C1 H1A 110.6 . . ?
O1 C1 C2 108.70(11) . . ?
O2 C1 H1A 110.6 . . ?
O2 C1 C2 112.15(10) . . ?
C2 C1 H1A 110.6 . . ?
C1 C2 H2A 108.2 . . ?
C1 C2 H2B 108.2 . . ?
C1 C2 C3 116.49(11) . . ?
H2A C2 H2B 107.3 . . ?
C3 C2 H2A 108.2 . . ?
C3 C2 H2B 108.2 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C2 C3 C4 113.90(11) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.35(11) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
O3 C5 C4 113.95(10) . . ?
O3 C5 H5 108.3 . . ?
O4 C5 O3 112.80(10) . . ?
O4 C5 C4 105.01(10) . . ?
O4 C5 H5 108.3 . . ?
C4 C5 H5 108.3 . . ?
O5 C6 C7 110.98(10) . . ?
O5 C6 C13 109.81(10) . . ?
O5 C6 C14 101.24(10) . . ?
C7 C6 C14 109.43(10) . . ?
C13 C6 C7 113.76(11) . . ?
C13 C6 C14 110.91(11) . . ?
C8 C7 C6 120.67(11) . . ?
C8 C7 C12 118.37(12) . . ?
C12 C7 C6 120.88(12) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.75(12) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.44(13) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.27(13) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.53(13) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.65(13) . . ?
C11 C12 H12 119.7 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O6 C15 O7 104.50(10) . . ?
O6 C15 H15 110.6 . . ?
O6 C15 C16 108.48(11) . . ?
O7 C15 H15 110.6 . . ?
O7 C15 C16 111.95(10) . . ?
C16 C15 H15 110.6 . . ?
C15 C16 H16A 108.2 . . ?
C15 C16 H16B 108.2 . . ?
C15 C16 C17 116.15(11) . . ?
H16A C16 H16B 107.4 . . ?
C17 C16 H16A 108.2 . . ?
C17 C16 H16B 108.2 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 C16 113.80(11) . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 C17 113.99(11) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
O8 C19 C18 113.73(10) . . ?
O8 C19 H19 108.1 . . ?
O9 C19 O8 112.88(10) . . ?
O9 C19 C18 105.78(10) . . ?
O9 C19 H19 108.1 . . ?
C18 C19 H19 108.1 . . ?
O10 C20 C21 110.55(10) . . ?
O10 C20 C27 109.56(10) . . ?
O10 C20 C28 100.92(10) . . ?
C21 C20 C28 110.03(10) . . ?
C27 C20 C21 113.85(11) . . ?
C27 C20 C28 111.19(11) . . ?
C22 C21 C20 120.09(12) . . ?
C26 C21 C20 121.59(12) . . ?
C26 C21 C22 118.26(12) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.85(12) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.36(13) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.35(13) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.34(13) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.85(13) . . ?
C25 C26 H26 119.6 . . ?
C20 C27 H27A 109.5 . . ?
C20 C27 H27B 109.5 . . ?
C20 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C20 C28 H28A 109.5 . . ?
C20 C28 H28B 109.5 . . ?
C20 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O8 0.86(2) 2.05(2) 2.8944(14) 167(2) . yes
O6 H6 O3 0.90(2) 2.01(2) 2.8921(14) 167(2) . yes

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
O1 C1 C2 C3 -164.30(11) . . . . ?
O2 O3 C5 O4 -69.54(12) . . . . ?
O2 O3 C5 C4 50.07(12) . . . . ?
O2 C1 C2 C3 -49.81(15) . . . . ?
O3 O2 C1 O1 -162.39(9) . . . . ?
O3 O2 C1 C2 80.30(12) . . . . ?
O4 O5 C6 C7 61.33(11) . . . . ?
O4 O5 C6 C13 -65.31(12) . . . . ?
O4 O5 C6 C14 177.40(9) . . . . ?
O5 O4 C5 O3 -77.47(11) . . . . ?
O5 O4 C5 C4 157.88(9) . . . . ?
O5 C6 C7 C8 22.11(16) . . . . ?
O5 C6 C7 C12 -161.15(11) . . . . ?
O6 C15 C16 C17 165.14(11) . . . . ?
O7 O8 C19 O9 71.27(12) . . . . ?
O7 O8 C19 C18 -49.24(12) . . . . ?
O7 C15 C16 C17 50.34(15) . . . . ?
O8 O7 C15 O6 161.96(9) . . . . ?
O8 O7 C15 C16 -80.83(12) . . . . ?
O9 O10 C20 C21 -60.23(12) . . . . ?
O9 O10 C20 C27 66.02(12) . . . . ?
O9 O10 C20 C28 -176.65(9) . . . . ?
O10 O9 C19 O8 79.57(11) . . . . ?
O10 O9 C19 C18 -155.47(9) . . . . ?
O10 C20 C21 C22 -30.14(16) . . . . ?
O10 C20 C21 C26 152.84(11) . . . . ?
C1 O2 O3 C5 -107.90(10) . . . . ?
C1 C2 C3 C4 61.79(15) . . . . ?
C2 C3 C4 C5 -81.51(14) . . . . ?
C3 C4 C5 O3 34.85(15) . . . . ?
C3 C4 C5 O4 158.78(10) . . . . ?
C5 O4 O5 C6 133.82(10) . . . . ?
C6 C7 C8 C9 176.98(11) . . . . ?
C6 C7 C12 C11 -176.74(12) . . . . ?
C7 C8 C9 C10 -0.30(19) . . . . ?
C8 C7 C12 C11 0.07(19) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C7 -0.2(2) . . . . ?
C12 C7 C8 C9 0.16(19) . . . . ?
C13 C6 C7 C8 146.55(12) . . . . ?
C13 C6 C7 C12 -36.71(16) . . . . ?
C14 C6 C7 C8 -88.79(14) . . . . ?
C14 C6 C7 C12 87.95(14) . . . . ?
C15 O7 O8 C19 107.97(10) . . . . ?
C15 C16 C17 C18 -62.20(15) . . . . ?
C16 C17 C18 C19 82.37(14) . . . . ?
C17 C18 C19 O8 -36.00(15) . . . . ?
C17 C18 C19 O9 -160.44(10) . . . . ?
C19 O9 O10 C20 -133.24(10) . . . . ?
C20 C21 C22 C23 -177.13(12) . . . . ?
C20 C21 C26 C25 177.08(12) . . . . ?
C21 C22 C23 C24 0.0(2) . . . . ?
C22 C21 C26 C25 0.01(19) . . . . ?
C22 C23 C24 C25 0.1(2) . . . . ?
C23 C24 C25 C26 -0.1(2) . . . . ?
C24 C25 C26 C21 0.1(2) . . . . ?
C26 C21 C22 C23 -0.02(19) . . . . ?
C27 C20 C21 C22 -153.96(12) . . . . ?
C27 C20 C21 C26 29.03(17) . . . . ?
C28 C20 C21 C22 80.46(15) . . . . ?
C28 C20 C21 C26 -96.55(14) . . . . ?

_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 1.222
_oxdiff_exptl_absorpt_empirical_full_min 0.811
