# 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_smh_1_auto
_database_code_depnum_ccdc_archive 'CCDC 2100831'
loop_
_audit_author_name
_audit_author_address
mohansun
; Institute of Materia Medica, Chinese Academy of Medical Sciences 
China
;
_audit_update_record             
;
2021-08-02 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_audit_creation_date             2021-03-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 O4'
_chemical_formula_sum            'C22 H20 O4'
_chemical_formula_weight         348.38
_chemical_absolute_configuration ad
_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                   11.34810(10)
_cell_length_b                   14.9237(2)
_cell_length_c                   19.9392(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3376.82(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    21338
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.0810
_cell_measurement_theta_min      3.6910
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.888
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
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    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29039
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.435
_diffrn_reflns_theta_min         3.700
_diffrn_ambient_temperature      293(2)
_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 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00 106.00   0.50    0.62    --  103.25 -95.00  -7.00  150
  2  ω     91.00 178.00   0.50    0.62    --  103.25  30.00-180.00  174
  3  ω     82.00 176.00   0.50    0.62    --  103.25  74.00-142.00  188
  4  ω     33.00 120.00   0.50    0.15    --   47.70  57.00-150.00  174
  5  ω    -23.00  28.00   0.50    0.15    --  -47.70  19.00   0.00  102
  6  ω    -23.00  28.00   0.50    0.15    --  -47.70  19.00 -60.00  102
  7  ω    -69.00  25.00   0.50    0.15    --  -47.70  74.00-142.00  188
  8  ω    -68.00 -28.00   0.50    0.62    -- -101.00  61.00 -30.00   80
  9  ω    -61.00 -28.00   0.50    0.62    -- -101.00  56.00   3.00   66
 10  ω    -68.00 -28.00   0.50    0.62    -- -101.00  61.00  60.00   80
 11  ω     31.00  75.00   0.50    0.62    --  103.25 -61.00  90.00   88
 12  ω     31.00  75.00   0.50    0.62    --  103.25 -61.00 150.00   88
 13  ω     31.00  75.00   0.50    0.62    --  103.25 -61.00 120.00   88
 14  ω     31.00  75.00   0.50    0.62    --  103.25 -61.00  60.00   88
 15  ω     31.00  68.00   0.50    0.62    --  103.25 -56.00-138.00   74
 16  ω    -27.00  30.00   0.50    0.15    --   47.70 -19.00  90.00  114
 17  ω   -173.00 -84.00   0.50    0.62    -- -101.00 -61.00  30.00  178
 18  ω   -119.00 -59.00   0.50    0.15    --  -47.70 -57.00  60.00  120
 19  ω   -173.00 -88.00   0.50    0.62    -- -101.00 -45.00 -90.00  170
 20  ω   -173.00 -84.00   0.50    0.62    -- -101.00 -61.00 -60.00  178
 21  ω   -126.00 -84.00   0.50    0.62    -- -101.00 -95.00  -7.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0860040000
_diffrn_orient_matrix_UB_12      -0.0754500000
_diffrn_orient_matrix_UB_13      0.0198278000
_diffrn_orient_matrix_UB_21      -0.0927749000
_diffrn_orient_matrix_UB_22      0.0383034000
_diffrn_orient_matrix_UB_23      -0.0486038000
_diffrn_orient_matrix_UB_31      0.0494656000
_diffrn_orient_matrix_UB_32      -0.0590929000
_diffrn_orient_matrix_UB_33      -0.0566547000
_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              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                6402
_reflns_number_total             6708
_reflns_odcompleteness_completeness 99.77
_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 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2670 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6708
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.053
_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)+(0.0446P)²+0.7523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0879
_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:
 C16(H16a,H16b), C42(H42a,H42b), C5(H5a,H5b), C6(H6a,H6b), C30(H30a,H30b),
 C29(H29a,H29b)
2.b Aromatic/amide H refined with riding coordinates:
 C37(H37), C22(H22), C34(H34), C10(H10), C40(H40), C14(H14), C12(H12),
 C11(H11), C18(H18), C21(H21), C38(H38), C19(H19), C47(H47), C44(H44), C45(H45),
  C48(H48)
2.c Idealised Me refined as rotating group:
 C51(H51a,H51b,H51c), C25(H25a,H25b,H25c)
2.d Idealised tetrahedral OH refined as rotating group:
 O26(H26), O49(H49), O52(H52), O15(H15), O23(H23), O41(H41)
;
_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
O26 O 0.17082(13) 0.15682(11) 0.71057(7) 0.0266(3) Uani 1 1 d . . . . .
H26 H 0.130602 0.150518 0.676732 0.040 Uiso 1 1 calc R U . . .
O50 O 0.01487(13) 0.59231(12) 0.30749(7) 0.0289(3) Uani 1 1 d . . . . .
O24 O 0.47564(13) 0.15845(12) 0.54318(7) 0.0295(3) Uani 1 1 d . . . . .
O49 O 0.09554(15) 0.32372(11) 0.75368(8) 0.0313(3) Uani 1 1 d . . . . .
H49 H 0.115589 0.276074 0.736664 0.047 Uiso 1 1 calc R U . . .
O52 O 0.32961(13) 0.58574(12) 0.46931(8) 0.0313(4) Uani 1 1 d . . . . .
H52 H 0.370017 0.598376 0.436551 0.047 Uiso 1 1 calc R U . . .
O15 O 1.01946(12) 0.17359(12) 0.60309(8) 0.0316(4) Uani 1 1 d . . . . .
H15 H 1.033046 0.158544 0.564299 0.047 Uiso 1 1 calc R U . . .
O23 O 0.41865(15) -0.15355(11) 0.96808(8) 0.0347(4) Uani 1 1 d . . . . .
H23 H 0.405628 -0.199152 0.946374 0.052 Uiso 1 1 calc R U . . .
O41 O -0.51790(13) 0.64596(14) 0.37764(8) 0.0372(4) Uani 1 1 d . . . . .
H41 H -0.532695 0.645500 0.337389 0.056 Uiso 1 1 calc R U . . .
C17 C 0.35909(18) 0.07855(15) 0.85490(10) 0.0242(4) Uani 1 1 d . . . . .
C35 C 0.05629(18) 0.59412(14) 0.37170(10) 0.0241(4) Uani 1 1 d . . . . .
C46 C 0.11463(18) 0.39259(16) 0.70872(11) 0.0269(5) Uani 1 1 d . . . . .
C8 C 0.37250(18) 0.16423(14) 0.74447(10) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.44005(18) 0.15826(14) 0.60861(10) 0.0238(4) Uani 1 1 d . . . . .
C9 C 0.28933(17) 0.15809(14) 0.69304(11) 0.0238(4) Uani 1 1 d . . . . .
C4 C 0.73594(19) 0.20242(14) 0.68836(11) 0.0237(4) Uani 1 1 d . . . . .
C33 C 0.21251(18) 0.59393(15) 0.45310(11) 0.0263(4) Uani 1 1 d . . . . .
C7 C 0.49243(18) 0.16917(14) 0.72601(10) 0.0235(4) Uani 1 1 d . . . . .
C2 C 0.52814(17) 0.16411(14) 0.65845(10) 0.0226(4) Uani 1 1 d . . . . .
C13 C 0.89919(17) 0.17000(15) 0.61479(11) 0.0258(4) Uani 1 1 d . . . . .
C37 C -0.21216(19) 0.56906(15) 0.35392(11) 0.0257(4) Uani 1 1 d . . . . .
H37 H -0.167520 0.535816 0.323741 0.031 Uiso 1 1 calc R U . . .
C36 C -0.02834(18) 0.60217(14) 0.42337(11) 0.0238(4) Uani 1 1 d . . . . .
C22 C 0.29806(19) -0.00023(16) 0.84014(11) 0.0277(5) Uani 1 1 d . . . . .
H22 H 0.243531 -0.000296 0.805319 0.033 Uiso 1 1 calc R U . . .
C20 C 0.39871(19) -0.07880(15) 0.92803(11) 0.0278(4) Uani 1 1 d . . . . .
C34 C 0.17580(19) 0.58986(15) 0.38684(11) 0.0257(4) Uani 1 1 d . . . . .
H34 H 0.230960 0.584286 0.352594 0.031 Uiso 1 1 calc R U . . .
C27 C -0.15720(18) 0.60688(14) 0.40994(10) 0.0234(4) Uani 1 1 d . . . . .
C10 C 0.32152(18) 0.15578(14) 0.62618(10) 0.0242(4) Uani 1 1 d . . . . .
H10 H 0.264015 0.152568 0.593030 0.029 Uiso 1 1 calc R U . . .
C31 C 0.01257(19) 0.60992(15) 0.48966(11) 0.0257(4) Uani 1 1 d . . . . .
C43 C 0.15334(18) 0.53674(15) 0.62214(11) 0.0274(5) Uani 1 1 d . . . . .
C40 C -0.34819(19) 0.66321(16) 0.44461(11) 0.0280(5) Uani 1 1 d . . . . .
H40 H -0.394584 0.693507 0.475667 0.034 Uiso 1 1 calc R U . . .
C16 C 0.33321(19) 0.16511(15) 0.81730(10) 0.0257(4) Uani 1 1 d . . . . .
H16A H 0.249080 0.176409 0.818887 0.031 Uiso 1 1 calc R U . . .
H16B H 0.372271 0.214202 0.840155 0.031 Uiso 1 1 calc R U . . .
C14 C 0.85605(19) 0.20546(15) 0.67391(11) 0.0254(4) Uani 1 1 d . . . . .
H14 H 0.907685 0.231622 0.704383 0.030 Uiso 1 1 calc R U . . .
C28 C -0.22843(19) 0.65252(15) 0.45660(11) 0.0254(4) Uani 1 1 d . . . . .
C42 C 0.1784(2) 0.61527(16) 0.57675(11) 0.0299(5) Uani 1 1 d . . . . .
H42A H 0.262961 0.624519 0.575084 0.036 Uiso 1 1 calc R U . . .
H42B H 0.143503 0.668506 0.596354 0.036 Uiso 1 1 calc R U . . .
C5 C 0.68702(19) 0.23988(15) 0.75252(11) 0.0265(4) Uani 1 1 d . . . . .
H5A H 0.657926 0.300114 0.744768 0.032 Uiso 1 1 calc R U . . .
H5B H 0.749016 0.243064 0.785923 0.032 Uiso 1 1 calc R U . . .
C12 C 0.82330(19) 0.13041(15) 0.56946(11) 0.0280(5) Uani 1 1 d . . . . .
H12 H 0.852294 0.105630 0.529969 0.034 Uiso 1 1 calc R U . . .
C3 C 0.65635(17) 0.16479(14) 0.64185(11) 0.0233(4) Uani 1 1 d . . . . .
C11 C 0.70326(18) 0.12786(14) 0.58327(11) 0.0257(4) Uani 1 1 d . . . . .
H11 H 0.652749 0.100792 0.552630 0.031 Uiso 1 1 calc R U . . .
C39 C -0.39884(19) 0.62942(16) 0.38726(11) 0.0287(5) Uani 1 1 d . . . . .
C6 C 0.58689(18) 0.18088(15) 0.77848(10) 0.0254(4) Uani 1 1 d . . . . .
H6A H 0.617984 0.122664 0.790933 0.031 Uiso 1 1 calc R U . . .
H6B H 0.552879 0.207998 0.818233 0.031 Uiso 1 1 calc R U . . .
C32 C 0.13310(19) 0.60542(15) 0.50573(11) 0.0258(4) Uani 1 1 d . . . . .
C18 C 0.44057(19) 0.07553(15) 0.90664(11) 0.0278(5) Uani 1 1 d . . . . .
H18 H 0.482834 0.127018 0.917207 0.033 Uiso 1 1 calc R U . . .
C30 C -0.0778(2) 0.62613(16) 0.54403(11) 0.0288(5) Uani 1 1 d . . . . .
H30A H -0.039745 0.651464 0.583253 0.035 Uiso 1 1 calc R U . . .
H30B H -0.114022 0.569824 0.556901 0.035 Uiso 1 1 calc R U . . .
C21 C 0.3169(2) -0.07840(16) 0.87619(11) 0.0294(5) Uani 1 1 d . . . . .
H21 H 0.275007 -0.130142 0.865768 0.035 Uiso 1 1 calc R U . . .
C38 C -0.33189(19) 0.58005(16) 0.34239(11) 0.0279(5) Uani 1 1 d . . . . .
H38 H -0.366935 0.554471 0.304831 0.033 Uiso 1 1 calc R U . . .
C19 C 0.4608(2) -0.00202(16) 0.94304(11) 0.0300(5) Uani 1 1 d . . . . .
H19 H 0.516100 -0.002271 0.977472 0.036 Uiso 1 1 calc R U . . .
C47 C 0.1583(2) 0.37733(16) 0.64504(11) 0.0309(5) Uani 1 1 d . . . . .
H47 H 0.174463 0.319308 0.630744 0.037 Uiso 1 1 calc R U . . .
C44 C 0.1093(2) 0.54987(16) 0.68645(12) 0.0292(5) Uani 1 1 d . . . . .
H44 H 0.091742 0.607725 0.700632 0.035 Uiso 1 1 calc R U . . .
C45 C 0.0908(2) 0.47879(16) 0.72990(12) 0.0301(5) Uani 1 1 d . . . . .
H45 H 0.062541 0.489069 0.773001 0.036 Uiso 1 1 calc R U . . .
C51 C 0.0971(2) 0.58405(17) 0.25374(11) 0.0309(5) Uani 1 1 d . . . . .
H51A H 0.055341 0.581869 0.211896 0.046 Uiso 1 1 calc R U . . .
H51B H 0.141974 0.530032 0.259279 0.046 Uiso 1 1 calc R U . . .
H51C H 0.149256 0.634683 0.253873 0.046 Uiso 1 1 calc R U . . .
C29 C -0.1718(2) 0.69050(16) 0.51813(11) 0.0289(5) Uani 1 1 d . . . . .
H29A H -0.230970 0.699996 0.552499 0.035 Uiso 1 1 calc R U . . .
H29B H -0.136102 0.747880 0.507656 0.035 Uiso 1 1 calc R U . . .
C48 C 0.1776(2) 0.44942(16) 0.60279(11) 0.0304(5) Uani 1 1 d . . . . .
H48 H 0.207786 0.438989 0.560137 0.037 Uiso 1 1 calc R U . . .
C25 C 0.3912(2) 0.13672(19) 0.49275(11) 0.0332(5) Uani 1 1 d . . . . .
H25A H 0.430142 0.131080 0.450223 0.050 Uiso 1 1 calc R U . . .
H25B H 0.333122 0.183378 0.490228 0.050 Uiso 1 1 calc R U . . .
H25C H 0.353481 0.081090 0.503870 0.050 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
O26 H26 0.8200 . ?
O26 C9 1.390(2) . ?
O50 C35 1.364(3) . ?
O50 C51 1.426(3) . ?
O24 C1 1.366(2) . ?
O24 C25 1.426(3) . ?
O49 H49 0.8200 . ?
O49 C46 1.381(3) . ?
O52 H52 0.8200 . ?
O52 C33 1.373(3) . ?
O15 H15 0.8200 . ?
O15 C13 1.386(2) . ?
O23 H23 0.8200 . ?
O23 C20 1.390(3) . ?
O41 H41 0.8200 . ?
O41 C39 1.387(3) . ?
C17 C22 1.396(3) . ?
C17 C16 1.522(3) . ?
C17 C18 1.386(3) . ?
C35 C36 1.413(3) . ?
C35 C34 1.391(3) . ?
C46 C47 1.382(3) . ?
C46 C45 1.381(3) . ?
C8 C9 1.397(3) . ?
C8 C7 1.412(3) . ?
C8 C16 1.519(3) . ?
C1 C2 1.412(3) . ?
C1 C10 1.390(3) . ?
C9 C10 1.383(3) . ?
C4 C14 1.394(3) . ?
C4 C5 1.502(3) . ?
C4 C3 1.411(3) . ?
C33 C34 1.387(3) . ?
C33 C32 1.394(3) . ?
C7 C2 1.409(3) . ?
C7 C6 1.508(3) . ?
C2 C3 1.492(3) . ?
C13 C14 1.382(3) . ?
C13 C12 1.381(3) . ?
C37 H37 0.9300 . ?
C37 C27 1.398(3) . ?
C37 C38 1.388(3) . ?
C36 C27 1.488(3) . ?
C36 C31 1.406(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.387(3) . ?
C20 C21 1.390(3) . ?
C20 C19 1.378(3) . ?
C34 H34 0.9300 . ?
C27 C28 1.408(3) . ?
C10 H10 0.9300 . ?
C31 C32 1.406(3) . ?
C31 C30 1.512(3) . ?
C43 C42 1.508(3) . ?
C43 C44 1.390(3) . ?
C43 C48 1.387(3) . ?
C40 H40 0.9300 . ?
C40 C28 1.389(3) . ?
C40 C39 1.376(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C14 H14 0.9300 . ?
C28 C29 1.497(3) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C32 1.514(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.528(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.390(3) . ?
C3 C11 1.397(3) . ?
C11 H11 0.9300 . ?
C39 C38 1.386(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C19 1.385(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C29 1.526(3) . ?
C21 H21 0.9300 . ?
C38 H38 0.9300 . ?
C19 H19 0.9300 . ?
C47 H47 0.9300 . ?
C47 C48 1.384(3) . ?
C44 H44 0.9300 . ?
C44 C45 1.386(3) . ?
C45 H45 0.9300 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C48 H48 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C9 O26 H26 109.5 . . ?
C35 O50 C51 118.79(16) . . ?
C1 O24 C25 118.31(16) . . ?
C46 O49 H49 109.5 . . ?
C33 O52 H52 109.5 . . ?
C13 O15 H15 109.5 . . ?
C20 O23 H23 109.5 . . ?
C39 O41 H41 109.5 . . ?
C22 C17 C16 121.00(19) . . ?
C18 C17 C22 117.4(2) . . ?
C18 C17 C16 121.5(2) . . ?
O50 C35 C36 116.85(18) . . ?
O50 C35 C34 122.59(19) . . ?
C34 C35 C36 120.6(2) . . ?
O49 C46 C47 122.0(2) . . ?
O49 C46 C45 117.66(19) . . ?
C45 C46 C47 120.3(2) . . ?
C9 C8 C7 117.61(18) . . ?
C9 C8 C16 120.27(18) . . ?
C7 C8 C16 122.11(18) . . ?
O24 C1 C2 117.56(18) . . ?
O24 C1 C10 121.78(18) . . ?
C10 C1 C2 120.61(19) . . ?
O26 C9 C8 118.05(18) . . ?
C10 C9 O26 119.85(18) . . ?
C10 C9 C8 122.08(18) . . ?
C14 C4 C5 121.68(19) . . ?
C14 C4 C3 120.20(19) . . ?
C3 C4 C5 118.11(19) . . ?
O52 C33 C34 120.73(19) . . ?
O52 C33 C32 117.36(19) . . ?
C34 C33 C32 121.90(19) . . ?
C8 C7 C6 120.70(18) . . ?
C2 C7 C8 121.58(19) . . ?
C2 C7 C6 117.72(18) . . ?
C1 C2 C3 122.31(18) . . ?
C7 C2 C1 118.20(18) . . ?
C7 C2 C3 119.49(18) . . ?
C14 C13 O15 118.54(19) . . ?
C12 C13 O15 121.37(19) . . ?
C12 C13 C14 120.08(19) . . ?
C27 C37 H37 119.3 . . ?
C38 C37 H37 119.3 . . ?
C38 C37 C27 121.4(2) . . ?
C35 C36 C27 122.71(19) . . ?
C31 C36 C35 117.90(19) . . ?
C31 C36 C27 119.33(19) . . ?
C17 C22 H22 119.2 . . ?
C21 C22 C17 121.5(2) . . ?
C21 C22 H22 119.2 . . ?
C21 C20 O23 122.6(2) . . ?
C19 C20 O23 117.3(2) . . ?
C19 C20 C21 120.0(2) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 C35 119.8(2) . . ?
C33 C34 H34 120.1 . . ?
C37 C27 C36 124.26(19) . . ?
C37 C27 C28 117.83(19) . . ?
C28 C27 C36 117.91(19) . . ?
C1 C10 H10 120.1 . . ?
C9 C10 C1 119.84(19) . . ?
C9 C10 H10 120.1 . . ?
C36 C31 C32 122.1(2) . . ?
C36 C31 C30 117.61(19) . . ?
C32 C31 C30 120.3(2) . . ?
C44 C43 C42 120.8(2) . . ?
C48 C43 C42 121.7(2) . . ?
C48 C43 C44 117.4(2) . . ?
C28 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C39 C40 C28 120.6(2) . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C8 C16 C17 114.01(17) . . ?
C8 C16 H16A 108.8 . . ?
C8 C16 H16B 108.8 . . ?
H16A C16 H16B 107.6 . . ?
C4 C14 H14 119.7 . . ?
C13 C14 C4 120.7(2) . . ?
C13 C14 H14 119.7 . . ?
C27 C28 C29 118.57(19) . . ?
C40 C28 C27 120.2(2) . . ?
C40 C28 C29 121.2(2) . . ?
C43 C42 H42A 108.5 . . ?
C43 C42 H42B 108.5 . . ?
C43 C42 C32 114.96(18) . . ?
H42A C42 H42B 107.5 . . ?
C32 C42 H42A 108.5 . . ?
C32 C42 H42B 108.5 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C4 C5 C6 110.42(18) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C13 C12 H12 120.2 . . ?
C13 C12 C11 119.5(2) . . ?
C11 C12 H12 120.2 . . ?
C4 C3 C2 118.75(19) . . ?
C11 C3 C4 117.56(19) . . ?
C11 C3 C2 123.67(19) . . ?
C12 C11 C3 121.9(2) . . ?
C12 C11 H11 119.1 . . ?
C3 C11 H11 119.1 . . ?
C40 C39 O41 117.2(2) . . ?
C40 C39 C38 120.2(2) . . ?
C38 C39 O41 122.7(2) . . ?
C7 C6 C5 111.12(18) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C33 C32 C31 117.6(2) . . ?
C33 C32 C42 119.78(19) . . ?
C31 C32 C42 122.6(2) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 C17 121.9(2) . . ?
C19 C18 H18 119.1 . . ?
C31 C30 H30A 109.8 . . ?
C31 C30 H30B 109.8 . . ?
C31 C30 C29 109.40(18) . . ?
H30A C30 H30B 108.2 . . ?
C29 C30 H30A 109.8 . . ?
C29 C30 H30B 109.8 . . ?
C22 C21 C20 119.5(2) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C37 C38 H38 120.2 . . ?
C39 C38 C37 119.5(2) . . ?
C39 C38 H38 120.2 . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C46 C47 H47 120.4 . . ?
C46 C47 C48 119.2(2) . . ?
C48 C47 H47 120.4 . . ?
C43 C44 H44 119.2 . . ?
C45 C44 C43 121.5(2) . . ?
C45 C44 H44 119.2 . . ?
C46 C45 C44 119.5(2) . . ?
C46 C45 H45 120.3 . . ?
C44 C45 H45 120.3 . . ?
O50 C51 H51A 109.5 . . ?
O50 C51 H51B 109.5 . . ?
O50 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C28 C29 C30 109.84(19) . . ?
C28 C29 H29A 109.7 . . ?
C28 C29 H29B 109.7 . . ?
C30 C29 H29A 109.7 . . ?
C30 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
C43 C48 H48 119.0 . . ?
C47 C48 C43 122.0(2) . . ?
C47 C48 H48 119.0 . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
O26 H26 O15 0.82 1.97 2.758(2) 162.1 1_455 yes
O49 H49 O26 0.82 1.96 2.770(2) 170.8 . yes
O52 H52 O41 0.82 1.87 2.673(2) 165.3 1_655 yes
O15 H15 O23 0.82 2.00 2.798(2) 165.5 2_654 yes
O41 H41 O49 0.82 1.87 2.663(2) 161.5 2_464 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
O26 C9 C10 C1 179.14(19) . . . . ?
O50 C35 C36 C27 1.1(3) . . . . ?
O50 C35 C36 C31 -176.03(19) . . . . ?
O50 C35 C34 C33 178.6(2) . . . . ?
O24 C1 C2 C7 176.43(19) . . . . ?
O24 C1 C2 C3 -3.8(3) . . . . ?
O24 C1 C10 C9 -178.3(2) . . . . ?
O49 C46 C47 C48 -178.8(2) . . . . ?
O49 C46 C45 C44 179.7(2) . . . . ?
O52 C33 C34 C35 177.01(19) . . . . ?
O52 C33 C32 C31 -177.28(19) . . . . ?
O52 C33 C32 C42 4.5(3) . . . . ?
O15 C13 C14 C4 -179.2(2) . . . . ?
O15 C13 C12 C11 179.7(2) . . . . ?
O23 C20 C21 C22 177.3(2) . . . . ?
O23 C20 C19 C18 -177.2(2) . . . . ?
O41 C39 C38 C37 177.5(2) . . . . ?
C17 C22 C21 C20 -0.4(3) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C35 C36 C27 C37 27.4(3) . . . . ?
C35 C36 C27 C28 -152.5(2) . . . . ?
C35 C36 C31 C32 -3.2(3) . . . . ?
C35 C36 C31 C30 175.10(19) . . . . ?
C46 C47 C48 C43 -0.7(4) . . . . ?
C8 C9 C10 C1 1.0(3) . . . . ?
C8 C7 C2 C1 3.0(3) . . . . ?
C8 C7 C2 C3 -176.77(19) . . . . ?
C8 C7 C6 C5 -144.3(2) . . . . ?
C1 C2 C3 C4 157.2(2) . . . . ?
C1 C2 C3 C11 -24.6(3) . . . . ?
C9 C8 C7 C2 -2.8(3) . . . . ?
C9 C8 C7 C6 176.72(19) . . . . ?
C9 C8 C16 C17 107.0(2) . . . . ?
C4 C5 C6 C7 -55.4(2) . . . . ?
C4 C3 C11 C12 -2.3(3) . . . . ?
C7 C8 C9 O26 -177.47(19) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C7 C8 C16 C17 -72.7(3) . . . . ?
C7 C2 C3 C4 -23.0(3) . . . . ?
C7 C2 C3 C11 155.2(2) . . . . ?
C2 C1 C10 C9 -0.7(3) . . . . ?
C2 C7 C6 C5 35.2(3) . . . . ?
C2 C3 C11 C12 179.6(2) . . . . ?
C13 C12 C11 C3 0.4(3) . . . . ?
C37 C27 C28 C40 -3.5(3) . . . . ?
C37 C27 C28 C29 177.8(2) . . . . ?
C36 C35 C34 C33 -0.3(3) . . . . ?
C36 C27 C28 C40 176.4(2) . . . . ?
C36 C27 C28 C29 -2.3(3) . . . . ?
C36 C31 C32 C33 0.8(3) . . . . ?
C36 C31 C32 C42 178.9(2) . . . . ?
C36 C31 C30 C29 -38.8(3) . . . . ?
C22 C17 C16 C8 -69.6(3) . . . . ?
C22 C17 C18 C19 -0.5(3) . . . . ?
C34 C35 C36 C27 -179.9(2) . . . . ?
C34 C35 C36 C31 2.9(3) . . . . ?
C34 C33 C32 C31 2.0(3) . . . . ?
C34 C33 C32 C42 -176.2(2) . . . . ?
C27 C37 C38 C39 -0.1(3) . . . . ?
C27 C36 C31 C32 179.6(2) . . . . ?
C27 C36 C31 C30 -2.1(3) . . . . ?
C27 C28 C29 C30 -38.7(3) . . . . ?
C10 C1 C2 C7 -1.3(3) . . . . ?
C10 C1 C2 C3 178.5(2) . . . . ?
C31 C36 C27 C37 -155.5(2) . . . . ?
C31 C36 C27 C28 24.6(3) . . . . ?
C31 C30 C29 C28 58.0(2) . . . . ?
C43 C42 C32 C33 -110.0(2) . . . . ?
C43 C42 C32 C31 71.9(3) . . . . ?
C43 C44 C45 C46 -1.1(3) . . . . ?
C40 C28 C29 C30 142.5(2) . . . . ?
C40 C39 C38 C37 -3.4(3) . . . . ?
C16 C17 C22 C21 -176.87(19) . . . . ?
C16 C17 C18 C19 177.1(2) . . . . ?
C16 C8 C9 O26 2.7(3) . . . . ?
C16 C8 C9 C10 -179.0(2) . . . . ?
C16 C8 C7 C2 177.0(2) . . . . ?
C16 C8 C7 C6 -3.5(3) . . . . ?
C14 C4 C5 C6 -142.5(2) . . . . ?
C14 C4 C3 C2 -178.9(2) . . . . ?
C14 C4 C3 C11 2.8(3) . . . . ?
C14 C13 C12 C11 1.0(3) . . . . ?
C28 C40 C39 O41 -177.5(2) . . . . ?
C28 C40 C39 C38 3.5(3) . . . . ?
C42 C43 C44 C45 -177.0(2) . . . . ?
C42 C43 C48 C47 177.9(2) . . . . ?
C5 C4 C14 C13 179.5(2) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C5 C4 C3 C11 -178.19(19) . . . . ?
C12 C13 C14 C4 -0.5(3) . . . . ?
C3 C4 C14 C13 -1.5(3) . . . . ?
C3 C4 C5 C6 38.5(3) . . . . ?
C39 C40 C28 C27 0.1(3) . . . . ?
C39 C40 C28 C29 178.8(2) . . . . ?
C6 C7 C2 C1 -176.47(19) . . . . ?
C6 C7 C2 C3 3.7(3) . . . . ?
C32 C33 C34 C35 -2.3(3) . . . . ?
C32 C31 C30 C29 139.5(2) . . . . ?
C18 C17 C22 C21 0.7(3) . . . . ?
C18 C17 C16 C8 112.9(2) . . . . ?
C30 C31 C32 C33 -177.5(2) . . . . ?
C30 C31 C32 C42 0.7(3) . . . . ?
C21 C20 C19 C18 0.5(3) . . . . ?
C38 C37 C27 C36 -176.4(2) . . . . ?
C38 C37 C27 C28 3.5(3) . . . . ?
C19 C20 C21 C22 -0.3(3) . . . . ?
C47 C46 C45 C44 1.0(3) . . . . ?
C44 C43 C42 C32 -133.7(2) . . . . ?
C44 C43 C48 C47 0.5(3) . . . . ?
C45 C46 C47 C48 -0.1(3) . . . . ?
C51 O50 C35 C36 -179.9(2) . . . . ?
C51 O50 C35 C34 1.2(3) . . . . ?
C48 C43 C42 C32 49.0(3) . . . . ?
C48 C43 C44 C45 0.4(3) . . . . ?
C25 O24 C1 C2 169.0(2) . . . . ?
C25 O24 C1 C10 -13.3(3) . . . . ?

_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 1.832
_oxdiff_exptl_absorpt_empirical_full_min 0.584
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
