# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_24pnv_r05_g
_database_code_depnum_ccdc_archive 'CCDC 2466682'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-06-23 deposited with the CCDC.	2025-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-12-26
_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        ?
_chemical_formula_moiety         'C14 H24 O4'
_chemical_formula_sum            'C14 H24 O4'
_chemical_formula_weight         256.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H24 O4'
_chemical_oxdiff_usercomment     DS-153
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/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                   6.37131(4)
_cell_length_b                   22.56666(17)
_cell_length_c                   19.24769(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.9112(6)
_cell_angle_gamma                90
_cell_volume                     2752.70(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    29018
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.4200
_cell_measurement_theta_min      3.0220
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.683
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.543
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (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            'clear colourless'
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0650
0 -1 1 0.0573
1 1 0 0.3289
-1 -1 0 0.1920
0 0 -1 0.0747
0 0 1 0.0519
0 1 0 0.0447
0 -1 0 0.0429
0 1 1 0.0399
0 -1 -1 0.0544

_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
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
-0.0006 1.0003 -0.9991 0.0400 0.0976 0.0021
0.0006 -1.0003 0.9991 -0.0400 -0.0976 -0.0021
0.9999 1.0002 0.0000 0.0291 0.0096 0.2506
-0.9999 -1.0002 -0.0000 -0.0291 -0.0096 -0.2506
-0.0004 0.0006 -1.0000 0.0683 0.0387 -0.0175
0.0004 -0.0006 1.0000 -0.0683 -0.0387 0.0175
-0.0002 0.9997 0.0008 -0.0283 0.0589 0.0196
0.0002 -0.9997 -0.0008 0.0283 -0.0589 -0.0196
0.0001 0.9991 1.0008 -0.0967 0.0202 0.0371
-0.0001 -0.9991 -1.0008 0.0967 -0.0202 -0.0371

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            44051
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.798
_diffrn_reflns_theta_min         3.027
_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
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00  14.00   0.50    0.86    --  -44.24 102.00 -13.00  188
  2  ω      8.00  82.00   0.50    0.86    --   44.24-102.00-115.00  148
  3  ω      8.00  82.00   0.50    0.86    --   44.24-102.00-115.00  148
  4  ω    -81.00 -24.00   0.50    3.44    --  -96.00 102.00 -13.00  114
  5  ω     46.00 107.00   0.50    3.44    --  117.50-102.00-115.00  122
  6  ω    106.00 178.00   0.50    3.44    --  117.50 102.00 -13.00  144
  7  ω    -27.00  35.00   0.50    0.86    --  -44.24  19.00 -30.00  124
  8  ω    -27.00  35.00   0.50    0.86    --  -44.24  19.00  90.00  124
  9  ω     12.00  43.00   0.50    0.86    --   44.24  88.00  92.20   62
 10  ω     34.00  94.00   0.50    0.86    --   44.24-125.00-180.00  120
 11  ω    -34.00  27.00   0.50    0.86    --   44.24 -19.00-150.00  122
 12  ω     12.00  43.00   0.50    0.86    --   44.24  89.00  37.84   62
 13  ω     34.00  94.00   0.50    0.86    --   44.24-125.00-180.00  120
 14  ω    -51.00 -21.00   0.50    3.44    --  -96.00  45.00-180.00   60
 15  ω   -168.00 -85.00   0.50    3.44    --  -96.00-102.00-115.00  166
 16  ω     45.00  71.00   0.50    3.44    --  117.50 -61.00 150.00   52
 17  ω     45.00  71.00   0.50    3.44    --  117.50 -61.00-120.00   52
 18  ω     97.00 178.00   0.50    3.44    --  117.50  61.00 -30.00  162
 19  ω     45.00 149.00   0.50    3.44    --  117.50 -87.00 -76.12  208
 20  ω     98.00 178.00   0.50    3.44    --  117.50  30.00 120.00  160
 21  ω     45.00  71.00   0.50    3.44    --  117.50 -61.00 -60.00   52
 22  ω     47.00 111.00   0.50    3.44    --  117.50-125.00 150.00  128
 23  ω     47.00 111.00   0.50    3.44    --  117.50-125.00   0.00  128
 24  ω     95.00 178.00   0.50    3.44    --  117.50 125.00 120.00  166
 25  ω     98.00 178.00   0.50    3.44    --  117.50  45.00 -60.00  160
 26  ω     47.00 111.00   0.50    3.44    --  117.50-125.00  30.00  128
 27  ω     91.00 142.00   0.50    3.44    --  117.50  77.00-180.00  102
 28  ω    149.00 175.00   0.50    3.44    --  117.50  77.00-180.00   52
 29  ω     49.00  91.00   0.50    3.44    --  117.50-125.00-180.00   84
 30  ω     95.00 147.00   0.50    3.44    --  117.50 125.00-150.00  104
 31  ω     73.00 119.00   0.50    3.44    --  117.50 -83.00-105.36   92
 32  ω     46.00  71.00   0.50    3.44    --  117.50 -77.00 -60.00   50
 33  ω     59.00 102.00   0.50    3.44    --  117.50 -95.00  30.00   86
 34  ω     99.00 130.00   0.50    3.44    --  117.50  30.00   0.00   62
 35  ω    149.00 174.00   0.50    3.44    --  117.50  30.00   0.00   50
 36  ω    120.00 171.00   0.50    3.44    --  117.50  61.00-150.00  102
 37  ω     51.00 101.00   0.50    3.44    --  117.50-102.00-101.87  100
 38  ω     67.00  93.00   0.50    3.44    --  117.50 -95.00-120.00   52
 39  ω     55.00 105.00   0.50    3.44    --  117.50 -77.00  30.00  100
 40  ω     62.00  88.00   0.50    3.44    --  117.50 -95.00  90.00   52
 41  ω     98.00 177.00   0.50    3.44    --  117.50  45.00  60.00  158
 42  ω    100.00 144.00   0.50    3.44    --  117.50 -80.00  86.84   88
 43  ω     47.00  88.00   0.50    3.44    --  117.50 -80.00  86.84   82
 44  ω     53.00  79.00   0.50    3.44    --  117.50-125.00-150.00   52
 45  ω     47.00 107.00   0.50    3.44    --  117.50-104.00 -48.73  120
 46  ω     49.00  90.00   0.50    3.44    --  117.50 -95.00 -90.00   82
 47  ω     98.00 128.00   0.50    3.44    --  117.50  45.00  30.00   60
 48  ω    111.00 137.00   0.50    3.44    --  117.50  30.00-180.00   52
 49  ω    113.00 139.00   0.50    3.44    --  117.50  77.00-150.00   52
 50  ω    104.00 174.00   0.50    3.44    --  117.50  77.00 -90.00  140
 51  ω    133.00 174.00   0.50    3.44    --  117.50  15.00 -30.00   82
 52  ω     90.00 116.00   0.50    3.44    --  117.50  15.00  30.00   52
 53  ω    112.00 150.00   0.50    3.44    --  117.50 -88.00-111.35   76
 54  ω    111.00 148.00   0.50    3.44    --  117.50 -88.00 169.97   74
 55  ω     45.00  70.00   0.50    3.44    --  117.50 -61.00 120.00   50
;
_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      0.0573925000
_diffrn_orient_matrix_UB_12      -0.0282879000
_diffrn_orient_matrix_UB_13      -0.0683868000
_diffrn_orient_matrix_UB_21      -0.0493893000
_diffrn_orient_matrix_UB_22      0.0589568000
_diffrn_orient_matrix_UB_23      -0.0386508000
_diffrn_orient_matrix_UB_31      0.2309718000
_diffrn_orient_matrix_UB_32      0.0196267000
_diffrn_orient_matrix_UB_33      0.0174369000
_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                5586
_reflns_number_total             6027
_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 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (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         0.309
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         6027
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.118
_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)+(0.0567P)²+0.6406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1117
_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:
 C2A(H1), C4A(H4A), C6A(H6A), C9A(H9A), C2B(H2C), C4B(H4B), C6B(H6B), C9B(H9B)
2.b Secondary CH2 refined with riding coordinates:
 C3A(H3A,H3B), C5A(H5A,H5B), C7A(H7A,H7B), C8A(H8A,H8B), C10A(H10A,H10B),
 C3B(H3C,H3D), C5B(H5C,H5D), C7B(H7C,H7D), C8B(H8C,H8D), C10B(H10C,H10D)
2.c Idealised Me refined as rotating group:
 C12A(H12A,H12B,H12C), C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C12B(H12D,
 H12E,H12F), C13B(H13D,H13E,H13F), C14B(H14D,H14E,H14F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O1A O 0.79239(10) 0.45080(3) 0.27745(3) 0.01531(14) Uani 1 1 d . . . . .
O2A O 0.89473(11) 0.48165(3) 0.22320(4) 0.01939(15) Uani 1 1 d . . . . .
H2A H 1.005(3) 0.4975(8) 0.2476(9) 0.043(4) Uiso 1 1 d . . . . .
O3A O 0.79614(9) 0.36577(3) 0.20801(3) 0.01522(15) Uani 1 1 d . . . . .
O4A O 0.56311(10) 0.36789(3) 0.19207(3) 0.01734(15) Uani 1 1 d . . . . .
C1A C 0.84167(13) 0.38884(4) 0.27571(4) 0.01315(18) Uani 1 1 d . . . . .
C2A C 0.70888(13) 0.36107(4) 0.32953(5) 0.01440(18) Uani 1 1 d . . . . .
H1 H 0.556103 0.369777 0.316278 0.017 Uiso 1 1 calc R U . . .
C3A C 0.74505(14) 0.29375(4) 0.32976(5) 0.01760(19) Uani 1 1 d . . . . .
H3A H 0.701101 0.277421 0.282772 0.021 Uiso 1 1 calc R U . . .
H3B H 0.658610 0.274733 0.363403 0.021 Uiso 1 1 calc R U . . .
C4A C 0.97971(14) 0.28018(4) 0.35032(5) 0.01831(19) Uani 1 1 d . . . . .
H4A H 1.002248 0.236321 0.350830 0.022 Uiso 1 1 calc R U . . .
C5A C 1.11270(14) 0.30882(4) 0.29721(5) 0.01726(19) Uani 1 1 d . . . . .
H5A H 1.072095 0.292040 0.250218 0.021 Uiso 1 1 calc R U . . .
H5B H 1.263935 0.300132 0.310261 0.021 Uiso 1 1 calc R U . . .
C6A C 1.07751(13) 0.37624(4) 0.29567(5) 0.01431(18) Uani 1 1 d . . . . .
H6A H 1.163371 0.394970 0.260948 0.017 Uiso 1 1 calc R U . . .
C7A C 0.77687(14) 0.38597(4) 0.40282(5) 0.01690(19) Uani 1 1 d . . . . .
H7A H 0.752506 0.429294 0.403205 0.020 Uiso 1 1 calc R U . . .
H7B H 0.691733 0.367541 0.437234 0.020 Uiso 1 1 calc R U . . .
C8A C 1.04738(15) 0.30562(4) 0.42324(5) 0.0196(2) Uani 1 1 d . . . . .
H8A H 0.964134 0.286862 0.457961 0.024 Uiso 1 1 calc R U . . .
H8B H 1.198373 0.296864 0.436658 0.024 Uiso 1 1 calc R U . . .
C9A C 1.01193(14) 0.37284(4) 0.42286(5) 0.01650(19) Uani 1 1 d . . . . .
H9A H 1.056507 0.389316 0.470324 0.020 Uiso 1 1 calc R U . . .
C10A C 1.14052(13) 0.40217(4) 0.36899(5) 0.01600(18) Uani 1 1 d . . . . .
H10A H 1.292873 0.395425 0.382356 0.019 Uiso 1 1 calc R U . . .
H10B H 1.114903 0.445447 0.368316 0.019 Uiso 1 1 calc R U . . .
C11A C 0.51829(14) 0.37009(4) 0.11683(5) 0.01686(19) Uani 1 1 d . . . . .
C12A C 0.27712(15) 0.36892(5) 0.10945(5) 0.0246(2) Uani 1 1 d . . . . .
H12A H 0.228531 0.332553 0.130566 0.037 Uiso 1 1 calc R U . . .
H12B H 0.223953 0.370041 0.059849 0.037 Uiso 1 1 calc R U . . .
H12C H 0.224269 0.403418 0.133219 0.037 Uiso 1 1 calc R U . . .
C13A C 0.60885(16) 0.31554(5) 0.08393(5) 0.0241(2) Uani 1 1 d . . . . .
H13A H 0.763259 0.317915 0.089004 0.036 Uiso 1 1 calc R U . . .
H13B H 0.557034 0.313833 0.034229 0.036 Uiso 1 1 calc R U . . .
H13C H 0.564479 0.279809 0.107391 0.036 Uiso 1 1 calc R U . . .
C14A C 0.60226(16) 0.42711(5) 0.08770(5) 0.0219(2) Uani 1 1 d . . . . .
H14A H 0.542961 0.461217 0.110410 0.033 Uiso 1 1 calc R U . . .
H14B H 0.561412 0.428951 0.037249 0.033 Uiso 1 1 calc R U . . .
H14C H 0.756459 0.427848 0.096690 0.033 Uiso 1 1 calc R U . . .
O1B O 0.29273(10) 0.52331(3) 0.27897(3) 0.01556(15) Uani 1 1 d . . . . .
O2B O 0.39368(11) 0.49285(3) 0.22407(4) 0.01939(16) Uani 1 1 d . . . . .
H2B H 0.508(3) 0.4782(7) 0.2476(8) 0.038(4) Uiso 1 1 d . . . . .
O3B O 0.29887(9) 0.60878(3) 0.21048(3) 0.01484(14) Uani 1 1 d . . . . .
O4B O 0.06580(9) 0.60702(3) 0.19439(3) 0.01713(15) Uani 1 1 d . . . . .
C1B C 0.34376(13) 0.58523(4) 0.27793(5) 0.01339(18) Uani 1 1 d . . . . .
C2B C 0.21169(13) 0.61284(4) 0.33207(5) 0.01470(18) Uani 1 1 d . . . . .
H2C H 0.058733 0.604436 0.318741 0.018 Uiso 1 1 calc R U . . .
C3B C 0.24925(14) 0.68016(4) 0.33284(5) 0.01787(19) Uani 1 1 d . . . . .
H3C H 0.205395 0.696807 0.286003 0.021 Uiso 1 1 calc R U . . .
H3D H 0.163403 0.699107 0.366695 0.021 Uiso 1 1 calc R U . . .
C4B C 0.48418(14) 0.69326(4) 0.35337(5) 0.01813(19) Uani 1 1 d . . . . .
H4B H 0.507656 0.737081 0.354190 0.022 Uiso 1 1 calc R U . . .
C5B C 0.61663(14) 0.66466(4) 0.30006(5) 0.01691(19) Uani 1 1 d . . . . .
H5C H 0.768054 0.673024 0.313197 0.020 Uiso 1 1 calc R U . . .
H5D H 0.576483 0.681719 0.253183 0.020 Uiso 1 1 calc R U . . .
C6B C 0.57974(13) 0.59731(4) 0.29808(5) 0.01403(18) Uani 1 1 d . . . . .
H6B H 0.665228 0.578583 0.263244 0.017 Uiso 1 1 calc R U . . .
C7B C 0.27887(14) 0.58749(4) 0.40510(5) 0.01760(19) Uani 1 1 d . . . . .
H7C H 0.193776 0.605816 0.439596 0.021 Uiso 1 1 calc R U . . .
H7D H 0.253766 0.544192 0.405110 0.021 Uiso 1 1 calc R U . . .
C8B C 0.55187(15) 0.66732(4) 0.42612(5) 0.0197(2) Uani 1 1 d . . . . .
H8C H 0.703305 0.675603 0.439361 0.024 Uiso 1 1 calc R U . . .
H8D H 0.469886 0.686213 0.461091 0.024 Uiso 1 1 calc R U . . .
C9B C 0.51393(14) 0.60021(4) 0.42546(5) 0.01693(19) Uani 1 1 d . . . . .
H9B H 0.557996 0.583448 0.472814 0.020 Uiso 1 1 calc R U . . .
C10B C 0.64205(14) 0.57090(4) 0.37124(5) 0.01644(18) Uani 1 1 d . . . . .
H10C H 0.615406 0.527671 0.370225 0.020 Uiso 1 1 calc R U . . .
H10D H 0.794556 0.577313 0.384666 0.020 Uiso 1 1 calc R U . . .
C11B C 0.02143(14) 0.60616(4) 0.11910(5) 0.01665(19) Uani 1 1 d . . . . .
C12B C -0.21938(15) 0.60859(5) 0.11161(5) 0.0246(2) Uani 1 1 d . . . . .
H12D H -0.274615 0.574384 0.135292 0.037 Uiso 1 1 calc R U . . .
H12E H -0.272400 0.607726 0.061989 0.037 Uiso 1 1 calc R U . . .
H12F H -0.265649 0.645213 0.132762 0.037 Uiso 1 1 calc R U . . .
C13B C 0.10168(16) 0.54925(5) 0.08870(5) 0.0227(2) Uani 1 1 d . . . . .
H13D H 0.255677 0.547470 0.098089 0.034 Uiso 1 1 calc R U . . .
H13E H 0.062016 0.548525 0.038143 0.034 Uiso 1 1 calc R U . . .
H13F H 0.039043 0.515085 0.110289 0.034 Uiso 1 1 calc R U . . .
C14B C 0.11629(16) 0.66076(5) 0.08754(5) 0.0232(2) Uani 1 1 d . . . . .
H14D H 0.076631 0.696275 0.112417 0.035 Uiso 1 1 calc R U . . .
H14E H 0.062820 0.663933 0.038092 0.035 Uiso 1 1 calc R U . . .
H14F H 0.270363 0.657133 0.091855 0.035 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
O1A O2A 1.4630(9) . ?
O1A C1A 1.4343(10) . ?
O2A H2A 0.879(18) . ?
O3A O4A 1.4856(8) . ?
O3A C1A 1.4054(10) . ?
O4A C11A 1.4477(11) . ?
C1A C2A 1.5369(12) . ?
C1A C6A 1.5387(11) . ?
C2A H1 1.0000 . ?
C2A C3A 1.5365(12) . ?
C2A C7A 1.5386(12) . ?
C3A H3A 0.9900 . ?
C3A H3B 0.9900 . ?
C3A C4A 1.5375(12) . ?
C4A H4A 1.0000 . ?
C4A C5A 1.5360(13) . ?
C4A C8A 1.5365(13) . ?
C5A H5A 0.9900 . ?
C5A H5B 0.9900 . ?
C5A C6A 1.5377(12) . ?
C6A H6A 1.0000 . ?
C6A C10A 1.5423(12) . ?
C7A H7A 0.9900 . ?
C7A H7B 0.9900 . ?
C7A C9A 1.5364(12) . ?
C8A H8A 0.9900 . ?
C8A H8B 0.9900 . ?
C8A C9A 1.5336(13) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.5360(12) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.5287(12) . ?
C11A C13A 1.5247(13) . ?
C11A C14A 1.5225(13) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
O1B O2B 1.4638(9) . ?
O1B C1B 1.4352(11) . ?
O2B H2B 0.879(17) . ?
O3B O4B 1.4859(8) . ?
O3B C1B 1.4048(10) . ?
O4B C11B 1.4479(11) . ?
C1B C2B 1.5371(12) . ?
C1B C6B 1.5379(11) . ?
C2B H2C 1.0000 . ?
C2B C3B 1.5378(13) . ?
C2B C7B 1.5369(12) . ?
C3B H3C 0.9900 . ?
C3B H3D 0.9900 . ?
C3B C4B 1.5369(12) . ?
C4B H4B 1.0000 . ?
C4B C5B 1.5362(13) . ?
C4B C8B 1.5379(13) . ?
C5B H5C 0.9900 . ?
C5B H5D 0.9900 . ?
C5B C6B 1.5378(12) . ?
C6B H6B 1.0000 . ?
C6B C10B 1.5431(12) . ?
C7B H7C 0.9900 . ?
C7B H7D 0.9900 . ?
C7B C9B 1.5356(12) . ?
C8B H8C 0.9900 . ?
C8B H8D 0.9900 . ?
C8B C9B 1.5336(13) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.5389(12) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.5271(12) . ?
C11B C13B 1.5216(13) . ?
C11B C14B 1.5257(13) . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 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
C1A O1A O2A 109.42(6) . . ?
O1A O2A H2A 101.7(11) . . ?
C1A O3A O4A 106.62(6) . . ?
C11A O4A O3A 107.32(6) . . ?
O1A C1A C2A 104.17(7) . . ?
O1A C1A C6A 112.63(7) . . ?
O3A C1A O1A 110.97(7) . . ?
O3A C1A C2A 113.49(7) . . ?
O3A C1A C6A 105.43(7) . . ?
C2A C1A C6A 110.34(7) . . ?
C1A C2A H1 109.7 . . ?
C1A C2A C7A 110.27(7) . . ?
C3A C2A C1A 108.20(7) . . ?
C3A C2A H1 109.7 . . ?
C3A C2A C7A 109.30(7) . . ?
C7A C2A H1 109.7 . . ?
C2A C3A H3A 109.7 . . ?
C2A C3A H3B 109.7 . . ?
C2A C3A C4A 109.83(7) . . ?
H3A C3A H3B 108.2 . . ?
C4A C3A H3A 109.7 . . ?
C4A C3A H3B 109.7 . . ?
C3A C4A H4A 109.5 . . ?
C5A C4A C3A 109.47(7) . . ?
C5A C4A H4A 109.5 . . ?
C5A C4A C8A 109.19(8) . . ?
C8A C4A C3A 109.55(8) . . ?
C8A C4A H4A 109.5 . . ?
C4A C5A H5A 109.7 . . ?
C4A C5A H5B 109.7 . . ?
C4A C5A C6A 109.86(7) . . ?
H5A C5A H5B 108.2 . . ?
C6A C5A H5A 109.7 . . ?
C6A C5A H5B 109.7 . . ?
C1A C6A H6A 110.0 . . ?
C1A C6A C10A 108.29(7) . . ?
C5A C6A C1A 108.93(7) . . ?
C5A C6A H6A 110.0 . . ?
C5A C6A C10A 109.52(7) . . ?
C10A C6A H6A 110.0 . . ?
C2A C7A H7A 109.8 . . ?
C2A C7A H7B 109.8 . . ?
H7A C7A H7B 108.2 . . ?
C9A C7A C2A 109.57(7) . . ?
C9A C7A H7A 109.8 . . ?
C9A C7A H7B 109.8 . . ?
C4A C8A H8A 109.7 . . ?
C4A C8A H8B 109.7 . . ?
H8A C8A H8B 108.2 . . ?
C9A C8A C4A 109.75(7) . . ?
C9A C8A H8A 109.7 . . ?
C9A C8A H8B 109.7 . . ?
C7A C9A H9A 109.6 . . ?
C8A C9A C7A 109.34(7) . . ?
C8A C9A H9A 109.6 . . ?
C8A C9A C10A 109.93(7) . . ?
C10A C9A C7A 108.74(7) . . ?
C10A C9A H9A 109.6 . . ?
C6A C10A H10A 109.6 . . ?
C6A C10A H10B 109.6 . . ?
C9A C10A C6A 110.33(7) . . ?
C9A C10A H10A 109.6 . . ?
C9A C10A H10B 109.6 . . ?
H10A C10A H10B 108.1 . . ?
O4A C11A C12A 100.67(7) . . ?
O4A C11A C13A 110.11(8) . . ?
O4A C11A C14A 110.90(8) . . ?
C13A C11A C12A 111.55(8) . . ?
C14A C11A C12A 111.61(8) . . ?
C14A C11A C13A 111.53(8) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11A C14A H14A 109.5 . . ?
C11A C14A H14B 109.5 . . ?
C11A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C1B O1B O2B 109.28(6) . . ?
O1B O2B H2B 101.8(10) . . ?
C1B O3B O4B 106.64(6) . . ?
C11B O4B O3B 107.27(6) . . ?
O1B C1B C2B 104.15(7) . . ?
O1B C1B C6B 112.71(7) . . ?
O3B C1B O1B 110.88(7) . . ?
O3B C1B C2B 113.56(7) . . ?
O3B C1B C6B 105.47(7) . . ?
C2B C1B C6B 110.27(7) . . ?
C1B C2B H2C 109.7 . . ?
C1B C2B C3B 108.14(7) . . ?
C3B C2B H2C 109.7 . . ?
C7B C2B C1B 110.42(7) . . ?
C7B C2B H2C 109.7 . . ?
C7B C2B C3B 109.30(7) . . ?
C2B C3B H3C 109.7 . . ?
C2B C3B H3D 109.7 . . ?
H3C C3B H3D 108.2 . . ?
C4B C3B C2B 109.82(7) . . ?
C4B C3B H3C 109.7 . . ?
C4B C3B H3D 109.7 . . ?
C3B C4B H4B 109.5 . . ?
C3B C4B C8B 109.59(8) . . ?
C5B C4B C3B 109.57(7) . . ?
C5B C4B H4B 109.5 . . ?
C5B C4B C8B 109.05(8) . . ?
C8B C4B H4B 109.5 . . ?
C4B C5B H5C 109.7 . . ?
C4B C5B H5D 109.7 . . ?
C4B C5B C6B 109.80(7) . . ?
H5C C5B H5D 108.2 . . ?
C6B C5B H5C 109.7 . . ?
C6B C5B H5D 109.7 . . ?
C1B C6B H6B 110.0 . . ?
C1B C6B C10B 108.34(7) . . ?
C5B C6B C1B 108.93(7) . . ?
C5B C6B H6B 110.0 . . ?
C5B C6B C10B 109.56(7) . . ?
C10B C6B H6B 110.0 . . ?
C2B C7B H7C 109.7 . . ?
C2B C7B H7D 109.7 . . ?
H7C C7B H7D 108.2 . . ?
C9B C7B C2B 109.65(7) . . ?
C9B C7B H7C 109.7 . . ?
C9B C7B H7D 109.7 . . ?
C4B C8B H8C 109.7 . . ?
C4B C8B H8D 109.7 . . ?
H8C C8B H8D 108.2 . . ?
C9B C8B C4B 109.83(7) . . ?
C9B C8B H8C 109.7 . . ?
C9B C8B H8D 109.7 . . ?
C7B C9B H9B 109.7 . . ?
C7B C9B C10B 108.55(7) . . ?
C8B C9B C7B 109.60(8) . . ?
C8B C9B H9B 109.7 . . ?
C8B C9B C10B 109.63(7) . . ?
C10B C9B H9B 109.7 . . ?
C6B C10B H10C 109.6 . . ?
C6B C10B H10D 109.6 . . ?
C9B C10B C6B 110.38(7) . . ?
C9B C10B H10C 109.6 . . ?
C9B C10B H10D 109.6 . . ?
H10C C10B H10D 108.1 . . ?
O4B C11B C12B 100.64(7) . . ?
O4B C11B C13B 110.94(8) . . ?
O4B C11B C14B 110.07(8) . . ?
C13B C11B C12B 111.60(8) . . ?
C13B C11B C14B 111.47(8) . . ?
C14B C11B C12B 111.65(8) . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C11B C14B H14D 109.5 . . ?
C11B C14B H14E 109.5 . . ?
C11B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 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
O2A H2A O1B 0.879(18) 1.960(18) 2.8118(9) 162.9(16) 1_655 yes
O2B H2B O1A 0.879(17) 1.947(17) 2.8056(9) 164.9(15) . 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
O1A C1A C2A C3A 178.06(7) . . . . ?
O1A C1A C2A C7A -62.45(9) . . . . ?
O1A C1A C6A C5A 176.21(7) . . . . ?
O1A C1A C6A C10A 57.17(9) . . . . ?
O2A O1A C1A O3A -52.18(8) . . . . ?
O2A O1A C1A C2A -174.66(6) . . . . ?
O2A O1A C1A C6A 65.76(8) . . . . ?
O3A O4A C11A C12A 177.30(7) . . . . ?
O3A O4A C11A C13A 59.46(9) . . . . ?
O3A O4A C11A C14A -64.46(9) . . . . ?
O3A C1A C2A C3A 57.25(9) . . . . ?
O3A C1A C2A C7A 176.74(7) . . . . ?
O3A C1A C6A C5A -62.63(9) . . . . ?
O3A C1A C6A C10A 178.33(7) . . . . ?
O4A O3A C1A O1A -67.29(8) . . . . ?
O4A O3A C1A C2A 49.61(9) . . . . ?
O4A O3A C1A C6A 170.48(6) . . . . ?
C1A O3A O4A C11A 155.17(7) . . . . ?
C1A C2A C3A C4A 60.54(9) . . . . ?
C1A C2A C7A C9A -58.78(10) . . . . ?
C1A C6A C10A C9A 60.68(9) . . . . ?
C2A C1A C6A C5A 60.27(9) . . . . ?
C2A C1A C6A C10A -58.77(9) . . . . ?
C2A C3A C4A C5A -60.39(10) . . . . ?
C2A C3A C4A C8A 59.31(10) . . . . ?
C2A C7A C9A C8A -60.31(10) . . . . ?
C2A C7A C9A C10A 59.74(9) . . . . ?
C3A C2A C7A C9A 60.04(9) . . . . ?
C3A C4A C5A C6A 59.41(9) . . . . ?
C3A C4A C8A C9A -59.50(10) . . . . ?
C4A C5A C6A C1A -59.04(9) . . . . ?
C4A C5A C6A C10A 59.23(9) . . . . ?
C4A C8A C9A C7A 60.02(10) . . . . ?
C4A C8A C9A C10A -59.29(9) . . . . ?
C5A C4A C8A C9A 60.37(10) . . . . ?
C5A C6A C10A C9A -57.98(9) . . . . ?
C6A C1A C2A C3A -60.82(9) . . . . ?
C6A C1A C2A C7A 58.67(9) . . . . ?
C7A C2A C3A C4A -59.56(9) . . . . ?
C7A C9A C10A C6A -61.52(9) . . . . ?
C8A C4A C5A C6A -60.52(9) . . . . ?
C8A C9A C10A C6A 58.15(9) . . . . ?
O1B C1B C2B C3B -177.86(7) . . . . ?
O1B C1B C2B C7B 62.59(9) . . . . ?
O1B C1B C6B C5B -176.43(7) . . . . ?
O1B C1B C6B C10B -57.31(9) . . . . ?
O2B O1B C1B O3B 51.89(8) . . . . ?
O2B O1B C1B C2B 174.39(6) . . . . ?
O2B O1B C1B C6B -66.08(8) . . . . ?
O3B O4B C11B C12B -176.40(7) . . . . ?
O3B O4B C11B C13B 65.38(9) . . . . ?
O3B O4B C11B C14B -58.48(9) . . . . ?
O3B C1B C2B C3B -57.14(9) . . . . ?
O3B C1B C2B C7B -176.68(7) . . . . ?
O3B C1B C6B C5B 62.46(9) . . . . ?
O3B C1B C6B C10B -178.42(7) . . . . ?
O4B O3B C1B O1B 67.11(8) . . . . ?
O4B O3B C1B C2B -49.75(9) . . . . ?
O4B O3B C1B C6B -170.60(6) . . . . ?
C1B O3B O4B C11B -155.91(7) . . . . ?
C1B C2B C3B C4B -60.52(9) . . . . ?
C1B C2B C7B C9B 58.88(10) . . . . ?
C1B C6B C10B C9B -60.70(9) . . . . ?
C2B C1B C6B C5B -60.51(9) . . . . ?
C2B C1B C6B C10B 58.61(9) . . . . ?
C2B C3B C4B C5B 60.28(10) . . . . ?
C2B C3B C4B C8B -59.33(10) . . . . ?
C2B C7B C9B C8B 59.97(9) . . . . ?
C2B C7B C9B C10B -59.74(10) . . . . ?
C3B C2B C7B C9B -59.96(9) . . . . ?
C3B C4B C5B C6B -59.32(10) . . . . ?
C3B C4B C8B C9B 59.16(10) . . . . ?
C4B C5B C6B C1B 59.10(9) . . . . ?
C4B C5B C6B C10B -59.25(9) . . . . ?
C4B C8B C9B C7B -59.51(10) . . . . ?
C4B C8B C9B C10B 59.54(9) . . . . ?
C5B C4B C8B C9B -60.77(10) . . . . ?
C5B C6B C10B C9B 58.02(9) . . . . ?
C6B C1B C2B C3B 60.97(9) . . . . ?
C6B C1B C2B C7B -58.57(9) . . . . ?
C7B C2B C3B C4B 59.73(9) . . . . ?
C7B C9B C10B C6B 61.50(9) . . . . ?
C8B C4B C5B C6B 60.62(9) . . . . ?
C8B C9B C10B C6B -58.19(9) . . . . ?

_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 1.261
_oxdiff_exptl_absorpt_empirical_full_min 0.747
