# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_exp_2527
_database_code_depnum_ccdc_archive 'CCDC 2132711'
loop_
_audit_author_name
_audit_author_address
'Weiqing Weiqing Xie'
;Northwest Agriculture and Forestry University
China
;
_audit_update_record             
;
2022-01-06 deposited with the CCDC.	2022-02-18 downloaded from the CCDC.
;
_audit_creation_date             2022-01-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 O3'
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.27
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.30150(10)
_cell_length_b                   11.6303(2)
_cell_length_c                   28.2622(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2399.99(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    34618
_cell_measurement_temperature    172.97(13)
_cell_measurement_theta_max      74.2760
_cell_measurement_theta_min      4.0900
_shelx_estimated_absorpt_T_max   0.822
_shelx_estimated_absorpt_T_min   0.765
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1048
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            54055
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.110
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.97(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00 -20.00   1.00    1.00    --    0.00 -57.00  60.00   52
  2  ω    -30.00  80.00   1.00    1.00    --    0.00  77.00 -60.00  110
  3  ω    -22.00  29.00   1.00    1.00    --    0.00  57.00 150.00   51
  4  ω     43.00  72.00   1.00    1.00    --    0.00  57.00 150.00   29
  5  ω    -24.00  26.00   1.00    1.00    --    0.00  19.00  60.00   50
  6  ω    -24.00  84.00   1.00    1.00    --    0.00  19.00 -90.00  108
  7  ω    -44.00  23.00   1.00    1.00    --    0.00 -57.00 120.00   67
  8  ω    -12.00  22.00   1.00    1.00    --    0.00 -57.00  60.00   34
  9  ω    -30.00  89.00   1.00    1.00    --    0.00  77.00  60.00  119
 10  ω     50.00  75.00   1.00    1.00    --    0.00  19.00  60.00   25
 11  ω    107.00 133.00   1.00    1.00    --   95.80  68.00   0.88   26
 12  ω    125.00 180.00   1.00    1.00    --   95.80  80.00-106.68   55
 13  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  73.91   25
 14  ω    101.00 175.00   1.00    1.00    --   95.80  82.00  73.91   74
 15  ω     64.00  94.00   1.00    1.00    --   95.80  80.00-106.68   30
 16  ω     68.00 101.00   1.00    1.00    --   95.80  68.00   0.88   33
 17  ω     72.00 185.00   1.00    1.00    --   95.80  59.00 -10.51  113
 18  ω    110.00 185.00   1.00    1.00    --   95.80  74.00 139.46   75
 19  ω     82.00 127.00   1.00    1.00    --   95.80 -82.00-120.00   45
 20  ω     37.00 102.00   1.00    1.00    --   95.80 -61.00-180.00   65
 21  ω     66.00  92.00   1.00    1.00    --   95.80  77.00-120.00   26
 22  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 23  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-180.00   26
 24  ω    144.00 180.00   1.00    1.00    --   95.80  82.00-180.00   36
 25  ω     66.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00   62
 26  ω     30.00 126.00   1.00    1.00    --   95.80 -82.00  90.00   96
 27  ω     65.00 102.00   1.00    1.00    --   95.80  77.00 -90.00   37
 28  ω     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 29  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 30  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
 31  ω     66.00  91.00   1.00    1.00    --   95.80  74.00 139.46   25
 32  ω    153.00 184.00   1.00    1.00    --   95.80  74.00-124.92   31
 33  ω     43.00 127.00   1.00    1.00    --   95.80 -82.00 171.84   84
 34  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 35  ω     75.00 185.00   1.00    1.00    --   95.80  45.00-120.00  110
 36  ω    137.00 173.00   1.00    1.00    --   95.80  63.00  39.87   36
 37  ω     75.00 102.00   1.00    1.00    --   95.80  45.00 150.00   27
 38  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 39  ω     66.00 169.00   1.00    1.00    --   95.80  74.00 -42.65  103
 40  ω     65.00 165.00   1.00    1.00    --   95.80  77.00 150.00  100
 41  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 42  ω     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 43  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 44  ω     64.00  90.00   1.00    1.00    --   95.80  82.00 -90.00   26
 45  ω     71.00  97.00   1.00    1.00    --   95.80  61.00-150.00   26
 46  ω     77.00 114.00   1.00    1.00    --   95.80 -77.00  30.00   37
 47  ω     76.00 184.00   1.00    1.00    --   95.80  45.00-150.00  108
 48  ω     70.00 132.00   1.00    1.00    --   95.80  63.00  39.87   62
 49  ω     65.00  91.00   1.00    1.00    --   95.80  82.00-120.00   26
 50  ω     71.00 108.00   1.00    1.00    --   95.80  61.00 150.00   37
 51  ω     64.00  90.00   1.00    1.00    --   95.80  82.00 150.00   26
 52  ω     96.00 183.00   1.00    1.00    --   95.80  82.00  90.00   87
 53  ω     65.00 173.00   1.00    1.00    --   95.80  78.00  47.31  108
 54  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 55  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 56  ω    143.00 173.00   1.00    1.00    --   95.80  68.00   0.88   30
 57  ω     66.00  91.00   1.00    1.00    --   95.80  74.00-124.92   25
 58  ω     69.00 172.00   1.00    1.00    --   95.80  65.00 -56.66  103
 59  ω     43.00 104.00   1.00    1.00    --   95.80 -82.00  30.00   61
 60  ω     71.00  97.00   1.00    1.00    --   95.80  61.00  90.00   26
 61  ω     71.00  96.00   1.00    1.00    --   95.80  59.00-158.82   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0213272000
_diffrn_orient_matrix_UB_12      0.0100364000
_diffrn_orient_matrix_UB_13      0.0540596000
_diffrn_orient_matrix_UB_21      0.2098795000
_diffrn_orient_matrix_UB_22      0.0040877000
_diffrn_orient_matrix_UB_23      0.0053682000
_diffrn_orient_matrix_UB_31      -0.0047078000
_diffrn_orient_matrix_UB_32      0.1320359000
_diffrn_orient_matrix_UB_33      -0.0043187000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4179
_reflns_number_total             4292
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1724 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_coef       0.0034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         4292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.5088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0793
_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.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C22(H22A,H22B), C23(H23A,H23B),
 C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C16(H16), C17(H17), C19(H19)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2106(2) 0.89966(13) 0.28152(5) 0.0291(3) Uani 1 1 d . . . . .
O2 O 0.0748(2) 0.89766(13) 0.20721(5) 0.0284(3) Uani 1 1 d . . . . .
H2 H 0.173864 0.913741 0.195264 0.043 Uiso 1 1 calc GR . . . .
O3 O 0.3997(2) 0.60869(15) 0.28852(6) 0.0417(4) Uani 1 1 d . . . . .
C1 C 0.0886(3) 0.94908(18) 0.31226(7) 0.0272(4) Uani 1 1 d . . . . .
C2 C 0.1301(3) 1.0361(2) 0.34416(8) 0.0343(5) Uani 1 1 d . . . . .
H2A H 0.246861 1.067751 0.345813 0.041 Uiso 1 1 calc R . . . .
C3 C -0.0107(4) 1.0740(2) 0.37359(7) 0.0358(6) Uani 1 1 d . . . . .
H3 H 0.014737 1.130890 0.395752 0.043 Uiso 1 1 calc R . . . .
C4 C -0.1874(4) 1.0301(2) 0.37115(8) 0.0346(5) Uani 1 1 d . . . . .
C5 C -0.2235(3) 0.94417(19) 0.33766(7) 0.0307(5) Uani 1 1 d . . . . .
H5 H -0.341296 0.914580 0.334746 0.037 Uiso 1 1 calc R . . . .
C6 C -0.0853(3) 0.90329(18) 0.30902(7) 0.0254(4) Uani 1 1 d . . . . .
C7 C -0.0845(3) 0.80867(18) 0.27233(6) 0.0239(4) Uani 1 1 d . . . . .
C8 C -0.0818(3) 0.68861(19) 0.29597(7) 0.0285(5) Uani 1 1 d . . . . .
H8A H -0.175591 0.686031 0.320255 0.034 Uiso 1 1 calc R . . . .
H8B H -0.111808 0.630952 0.272412 0.034 Uiso 1 1 calc R . . . .
C9 C 0.1021(3) 0.65886(19) 0.31813(7) 0.0325(5) Uani 1 1 d . . . . .
H9A H 0.129799 0.714337 0.342741 0.039 Uiso 1 1 calc R . . . .
H9B H 0.094129 0.583598 0.332776 0.039 Uiso 1 1 calc R . . . .
C10 C 0.2542(3) 0.65849(18) 0.28261(8) 0.0298(5) Uani 1 1 d . . . . .
C11 C 0.2171(3) 0.72537(19) 0.23779(7) 0.0268(5) Uani 1 1 d . . . . .
H11A H 0.152886 0.676570 0.215444 0.032 Uiso 1 1 calc R . . . .
H11B H 0.332539 0.747965 0.223559 0.032 Uiso 1 1 calc R . . . .
C12 C 0.1030(3) 0.83200(18) 0.24762(6) 0.0233(4) Uani 1 1 d . . . . .
C13 C -0.2482(3) 0.8149(2) 0.23900(8) 0.0321(5) Uani 1 1 d . . . . .
H13A H -0.358053 0.796876 0.256130 0.048 Uiso 1 1 calc GR . . . .
H13B H -0.232235 0.760661 0.213725 0.048 Uiso 1 1 calc GR . . . .
H13C H -0.257507 0.891073 0.226139 0.048 Uiso 1 1 calc GR . . . .
C14 C -0.3357(5) 1.0721(3) 0.40396(11) 0.0574(8) Uani 1 1 d . . . . .
H14A H -0.281111 1.111316 0.430304 0.086 Uiso 1 1 calc GR . . . .
H14B H -0.405474 1.007712 0.415243 0.086 Uiso 1 1 calc GR . . . .
H14C H -0.414895 1.123901 0.387230 0.086 Uiso 1 1 calc GR . . . .
O4 O 0.60340(19) 0.45308(13) 0.34136(4) 0.0267(3) Uani 1 1 d . . . . .
H4 H 0.525485 0.497138 0.330968 0.040 Uiso 1 1 calc GR . . . .
O5 O 0.66755(18) 0.58547(12) 0.40028(5) 0.0246(3) Uani 1 1 d . . . . .
O6 O 0.9541(2) 0.36538(18) 0.47605(6) 0.0471(5) Uani 1 1 d . . . . .
C15 C 0.5087(3) 0.64206(18) 0.41347(7) 0.0226(4) Uani 1 1 d . . . . .
C16 C 0.4898(3) 0.76016(19) 0.41546(7) 0.0271(5) Uani 1 1 d . . . . .
H16 H 0.586675 0.809046 0.408252 0.033 Uiso 1 1 calc R . . . .
C17 C 0.3197(3) 0.80245(19) 0.42873(7) 0.0268(4) Uani 1 1 d . . . . .
H17 H 0.303126 0.881648 0.430248 0.032 Uiso 1 1 calc R . . . .
C18 C 0.1731(3) 0.73121(19) 0.43982(6) 0.0231(4) Uani 1 1 d . . . . .
C19 C 0.1997(3) 0.61185(18) 0.43812(6) 0.0219(4) Uani 1 1 d . . . . .
H19 H 0.104823 0.562278 0.446192 0.026 Uiso 1 1 calc R . . . .
C20 C 0.3680(3) 0.56805(17) 0.42435(6) 0.0206(4) Uani 1 1 d . . . . .
C21 C 0.4334(3) 0.44561(18) 0.41775(7) 0.0217(4) Uani 1 1 d . . . . .
C22 C 0.4698(3) 0.3877(2) 0.46600(7) 0.0294(5) Uani 1 1 d . . . . .
H22A H 0.368389 0.404221 0.487088 0.035 Uiso 1 1 calc R . . . .
H22B H 0.474978 0.305061 0.461568 0.035 Uiso 1 1 calc R . . . .
C23 C 0.6472(3) 0.4277(2) 0.48914(7) 0.0360(5) Uani 1 1 d . . . . .
H23A H 0.644976 0.510573 0.492834 0.043 Uiso 1 1 calc R . . . .
H23B H 0.658193 0.393476 0.520316 0.043 Uiso 1 1 calc R . . . .
C24 C 0.8081(3) 0.3938(2) 0.45950(8) 0.0295(5) Uani 1 1 d . . . . .
C25 C 0.7766(3) 0.39346(19) 0.40654(7) 0.0258(4) Uani 1 1 d . . . . .
H25A H 0.886921 0.420440 0.390972 0.031 Uiso 1 1 calc R . . . .
H25B H 0.755174 0.314993 0.396307 0.031 Uiso 1 1 calc R . . . .
C26 C 0.6175(3) 0.46708(17) 0.39075(7) 0.0217(4) Uani 1 1 d . . . . .
C27 C 0.3003(3) 0.37030(19) 0.38987(8) 0.0297(5) Uani 1 1 d . . . . .
H27A H 0.195929 0.352758 0.409211 0.045 Uiso 1 1 calc GR . . . .
H27B H 0.360371 0.300208 0.380850 0.045 Uiso 1 1 calc GR . . . .
H27C H 0.261026 0.410588 0.362013 0.045 Uiso 1 1 calc GR . . . .
C28 C -0.0112(3) 0.7803(2) 0.45189(8) 0.0315(5) Uani 1 1 d . . . . .
H28A H -0.012059 0.804197 0.484409 0.047 Uiso 1 1 calc GR . . . .
H28B H -0.103730 0.722902 0.447036 0.047 Uiso 1 1 calc GR . . . .
H28C H -0.035685 0.845374 0.431946 0.047 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.370(3) . ?
O1 C12 1.468(2) . ?
O2 H2 0.8200 . ?
O2 C12 1.389(2) . ?
O3 C10 1.221(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.380(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.393(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(4) . ?
C4 C5 1.401(3) . ?
C4 C14 1.507(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(3) . ?
C6 C7 1.512(3) . ?
C7 C8 1.548(3) . ?
C7 C12 1.560(3) . ?
C7 C13 1.524(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.522(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.497(3) . ?
C10 C11 1.511(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.520(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O4 H4 0.8200 . ?
O4 C26 1.409(2) . ?
O5 C15 1.385(2) . ?
O5 C26 1.450(2) . ?
O6 C24 1.210(3) . ?
C15 C16 1.382(3) . ?
C15 C20 1.375(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(3) . ?
C18 C19 1.403(3) . ?
C18 C28 1.501(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(3) . ?
C20 C21 1.514(3) . ?
C21 C22 1.544(3) . ?
C21 C26 1.566(3) . ?
C21 C27 1.527(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.523(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.496(3) . ?
C24 C25 1.514(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.510(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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 C12 106.91(15) . . ?
C12 O2 H2 109.5 . . ?
O1 C1 C2 125.1(2) . . ?
O1 C1 C6 113.20(18) . . ?
C6 C1 C2 121.7(2) . . ?
C1 C2 H2A 121.4 . . ?
C1 C2 C3 117.2(2) . . ?
C3 C2 H2A 121.4 . . ?
C2 C3 H3 118.7 . . ?
C4 C3 C2 122.6(2) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 C5 118.0(2) . . ?
C3 C4 C14 121.2(2) . . ?
C5 C4 C14 120.8(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 108.82(18) . . ?
C5 C6 C1 120.1(2) . . ?
C5 C6 C7 131.1(2) . . ?
C6 C7 C8 111.13(15) . . ?
C6 C7 C12 100.60(16) . . ?
C6 C7 C13 112.71(18) . . ?
C8 C7 C12 109.83(17) . . ?
C13 C7 C8 108.63(17) . . ?
C13 C7 C12 113.78(15) . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 113.19(18) . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 112.29(17) . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
O3 C10 C9 123.7(2) . . ?
O3 C10 C11 121.0(2) . . ?
C9 C10 C11 115.32(19) . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C10 C11 C12 111.41(17) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
O1 C12 C7 105.70(15) . . ?
O1 C12 C11 105.26(16) . . ?
O2 C12 O1 108.73(16) . . ?
O2 C12 C7 109.50(16) . . ?
O2 C12 C11 112.30(16) . . ?
C11 C12 C7 114.90(17) . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C26 O4 H4 109.5 . . ?
C15 O5 C26 106.87(15) . . ?
C16 C15 O5 124.53(19) . . ?
C20 C15 O5 112.85(17) . . ?
C20 C15 C16 122.6(2) . . ?
C15 C16 H16 121.5 . . ?
C15 C16 C17 116.9(2) . . ?
C17 C16 H16 121.5 . . ?
C16 C17 H17 118.7 . . ?
C16 C17 C18 122.6(2) . . ?
C18 C17 H17 118.7 . . ?
C17 C18 C19 118.39(19) . . ?
C17 C18 C28 121.0(2) . . ?
C19 C18 C28 120.60(19) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.77(19) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 119.66(19) . . ?
C15 C20 C21 109.01(17) . . ?
C19 C20 C21 131.32(18) . . ?
C20 C21 C22 110.84(16) . . ?
C20 C21 C26 100.43(15) . . ?
C20 C21 C27 113.73(17) . . ?
C22 C21 C26 110.63(16) . . ?
C27 C21 C22 108.36(18) . . ?
C27 C21 C26 112.73(16) . . ?
C21 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 C21 113.11(18) . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C22 C23 H23A 109.6 . . ?
C22 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C24 C23 C22 110.30(18) . . ?
C24 C23 H23A 109.6 . . ?
C24 C23 H23B 109.6 . . ?
O6 C24 C23 123.2(2) . . ?
O6 C24 C25 121.0(2) . . ?
C23 C24 C25 115.75(17) . . ?
C24 C25 H25A 108.7 . . ?
C24 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C26 C25 C24 114.06(17) . . ?
C26 C25 H25A 108.7 . . ?
C26 C25 H25B 108.7 . . ?
O4 C26 O5 108.19(15) . . ?
O4 C26 C21 113.68(16) . . ?
O4 C26 C25 106.46(16) . . ?
O5 C26 C21 106.10(15) . . ?
O5 C26 C25 106.84(16) . . ?
C25 C26 C21 115.20(16) . . ?
C21 C27 H27A 109.5 . . ?
C21 C27 H27B 109.5 . . ?
C21 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C18 C28 H28A 109.5 . . ?
C18 C28 H28B 109.5 . . ?
C18 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_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 609.711
_oxdiff_exptl_absorpt_empirical_full_min 0.353
