# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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. 
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data_7a
_database_code_depnum_ccdc_archive 'CCDC 2072295'
loop_
_audit_author_name
_audit_author_address
'Andrei S. Batsanov'
;Durham University
United Kingdom
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;

_audit_creation_date             2020-11-27
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6208)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        
"Rac-(2aR,4aR,11aR)-4a-butyl-4a,10-dihydrocyclobuta[3a',4']pentaleno- [1',2':1,2]indeno[5,6-d][1,3]dioxol-11(2aH)-one"
_chemical_formula_moiety         'C22 H20 O3'
_chemical_formula_sum            'C22 H20 O3'
_chemical_formula_weight         332.38
_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 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7532(2)
_cell_length_b                   9.4136(3)
_cell_length_c                   14.1529(4)
_cell_angle_alpha                109.2492(11)
_cell_angle_beta                 93.9771(13)
_cell_angle_gamma                92.7275(13)
_cell_volume                     845.01(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6384
_cell_measurement_temperature    200
_cell_measurement_theta_max      30.93
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
wR2(int) was 0.1162 before and 0.0526 after correction.
The Ratio of minimum to maximum transmission is 0.9131.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 -1.00 0.1010
1.00 1.00 0.00 0.1110
-1.00 0.00 -1.00 0.1260
1.00 0.00 1.00 0.0900
0.00 -1.00 0.00 0.1060
0.00 0.00 1.00 0.0240
0.00 0.00 -1.00 0.0530
-2.00 -2.00 -1.00 0.1150
-2.00 1.00 -2.00 0.1220
1.00 -2.00 1.00 0.1310
1.00 0.00 -1.00 0.1290
-1.00 0.00 1.00 0.1130
1.00 2.00 2.00 0.0870

_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.106
_exptl_special_details           
; Phase transition at ca. 180 K. 
 At 293 K: a=6.829(3), b=9.482(4), c=14.242(8) Å, α=108.88(2), 
 β=95.07(2), γ=91.94(1) °, V=867(1) Å³. 
 At 240 K: a=6.787(2), b=9.451(3), c=14.190(7) Å, α=109.111(14), 
 β=94.318(15), γ=92.397(9) °, V=855.5(1.0) Å³.
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of 175 narrow-frame ω-scans (scan 
width 1°, 3s exposure), every run at a different φ angle.
One run of 358 φ-scans (scan width 1°, 1s exposure) was used for 
scaling overflowing intensities. Crystal to detector distance 3.49 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12919
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.296
_diffrn_ambient_temperature      200
_diffrn_detector                 'Bruker PHOTON III MM CPAD'
_diffrn_detector_area_resol_mean 7.4
_diffrn_detector_type            'CPA sensor'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω- and φ-scan'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\mS 3.0 microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3064
_reflns_number_total             3870
_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_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'APEX3 v.2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT v8.40A (Bruker AXS, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015a)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         3870
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.025
_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)+(0.0557P)²+0.2320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1178
_refine_special_details          ?

_atom_sites_solution_hydrogens   difmap
_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 0.00195(15) 0.80544(11) 0.11674(8) 0.0328(3) Uani 1 1 d . . . . .
O2 O 0.91766(15) 0.27367(11) 0.18792(8) 0.0321(3) Uani 1 1 d . . . . .
O3 O 0.73765(15) 0.10587(11) 0.04780(8) 0.0315(3) Uani 1 1 d . . . . .
C1 C 0.1866(2) 1.02132(18) 0.31945(13) 0.0375(4) Uani 1 1 d . . . . .
H1 H 0.082(3) 1.018(2) 0.3652(14) 0.049(5) Uiso 1 1 d . . . . .
C2 C 0.2877(3) 1.12684(18) 0.29610(14) 0.0448(5) Uani 1 1 d . . . . .
H2 H 0.292(3) 1.241(2) 0.3176(15) 0.062(6) Uiso 1 1 d . . . . .
C3 C 0.4051(2) 1.01784(16) 0.22073(13) 0.0337(4) Uani 1 1 d . . . . .
H3 H 0.384(3) 1.019(2) 0.1499(14) 0.042(5) Uiso 1 1 d . . . . .
C4 C 0.6148(2) 1.00125(18) 0.25415(12) 0.0348(4) Uani 1 1 d . . . . .
H4 H 0.730(3) 1.069(2) 0.2513(13) 0.045(5) Uiso 1 1 d . . . . .
C5 C 0.6311(2) 0.88794(16) 0.28910(11) 0.0290(3) Uani 1 1 d . . . . .
H5 H 0.751(3) 0.859(2) 0.3146(13) 0.041(5) Uiso 1 1 d . . . . .
C6 C 0.4354(2) 0.80066(15) 0.28522(10) 0.0228(3) Uani 1 1 d . . . . .
C7 C 0.2801(2) 0.89100(15) 0.24695(10) 0.0249(3) Uani 1 1 d . . . . .
C8 C 0.1521(2) 0.77768(15) 0.15853(10) 0.0237(3) Uani 1 1 d . . . . .
C9 C 0.2503(2) 0.63767(15) 0.13462(10) 0.0220(3) Uani 1 1 d . . . . .
C10 C 0.4100(2) 0.65181(14) 0.20089(10) 0.0212(3) Uani 1 1 d . . . . .
C11 C 0.5147(2) 0.51448(14) 0.17243(10) 0.0213(3) Uani 1 1 d . . . . .
C12 C 0.6921(2) 0.47863(16) 0.21371(10) 0.0242(3) Uani 1 1 d . . . . .
H12 H 0.769(2) 0.5486(18) 0.2718(12) 0.029(4) Uiso 1 1 d . . . . .
C13 C 0.7522(2) 0.33864(15) 0.16347(10) 0.0242(3) Uani 1 1 d . . . . .
C14 C 0.6437(2) 0.23773(15) 0.07886(11) 0.0244(3) Uani 1 1 d . . . . .
C15 C 0.4689(2) 0.26971(15) 0.03720(10) 0.0241(3) Uani 1 1 d . . . . .
H15 H 0.396(2) 0.1979(18) -0.0232(12) 0.027(4) Uiso 1 1 d . . . . .
C16 C 0.4059(2) 0.41272(15) 0.08554(10) 0.0217(3) Uani 1 1 d . . . . .
C17 C 0.2281(2) 0.48519(15) 0.05581(10) 0.0228(3) Uani 1 1 d . . . . .
H17A H 0.231(2) 0.4877(18) -0.0129(12) 0.029(4) Uiso 1 1 d . . . . .
H17B H 0.101(2) 0.4302(18) 0.0562(11) 0.027(4) Uiso 1 1 d . . . . .
C18 C 0.9317(2) 0.14201(17) 0.10156(12) 0.0316(3) Uani 1 1 d . . . . .
H18A H 1.025(2) 0.1651(18) 0.0587(12) 0.030(4) Uiso 1 1 d . . . . .
H18B H 0.972(2) 0.0619(19) 0.1268(12) 0.034(4) Uiso 1 1 d . . . . .
C19 C 0.3965(2) 0.78211(18) 0.38671(11) 0.0306(3) Uani 1 1 d . . . . .
H19A H 0.408(3) 0.886(2) 0.4393(13) 0.040(5) Uiso 1 1 d . . . . .
H19B H 0.505(3) 0.7285(19) 0.4053(12) 0.035(4) Uiso 1 1 d . . . . .
C20 C 0.1955(3) 0.7000(2) 0.38544(13) 0.0413(4) Uani 1 1 d . . . . .
H20A H 0.201(3) 0.594(2) 0.3427(14) 0.046(5) Uiso 1 1 d . . . . .
H20B H 0.083(3) 0.746(2) 0.3500(15) 0.060(6) Uiso 1 1 d . . . . .
C21 C 0.1374(4) 0.7090(3) 0.48910(17) 0.0711(7) Uani 1 1 d . . . . .
H21A H -0.013(4) 0.665(3) 0.4914(16) 0.071(7) Uiso 1 1 d . . . . .
H21B H 0.151(4) 0.818(3) 0.536(2) 0.097(9) Uiso 1 1 d . . . . .
C22 C 0.2643(6) 0.6258(4) 0.5391(2) 0.1001(12) Uani 1 1 d . . . . .
H22A H 0.206(5) 0.628(4) 0.600(3) 0.126(11) Uiso 1 1 d . . . . .
H22B H 0.265(5) 0.511(4) 0.489(2) 0.108(10) Uiso 1 1 d . . . . .
H22C H 0.420(5) 0.667(4) 0.549(2) 0.128(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.2207(16) . ?
O2 C13 1.3757(16) . ?
O2 C18 1.4379(18) . ?
O3 C14 1.3748(16) . ?
O3 C18 1.4354(18) . ?
C1 H1 1.00(2) . ?
C1 C2 1.321(3) . ?
C1 C7 1.514(2) . ?
C2 H2 1.01(2) . ?
C2 C3 1.514(2) . ?
C3 H3 1.006(18) . ?
C3 C4 1.493(2) . ?
C3 C7 1.586(2) . ?
C4 H4 0.994(19) . ?
C4 C5 1.321(2) . ?
C5 H5 0.950(19) . ?
C5 C6 1.511(2) . ?
C6 C7 1.5574(18) . ?
C6 C10 1.5045(18) . ?
C6 C19 1.541(2) . ?
C7 C8 1.5276(19) . ?
C8 C9 1.4533(18) . ?
C9 C10 1.3505(18) . ?
C9 C17 1.4925(18) . ?
C10 C11 1.4547(18) . ?
C11 C12 1.4010(19) . ?
C11 C16 1.4143(18) . ?
C12 H12 0.964(16) . ?
C12 C13 1.3712(19) . ?
C13 C14 1.391(2) . ?
C14 C15 1.3737(19) . ?
C15 H15 0.978(16) . ?
C15 C16 1.3960(18) . ?
C16 C17 1.5105(18) . ?
C17 H17A 0.982(16) . ?
C17 H17B 0.981(16) . ?
C18 H18A 0.971(17) . ?
C18 H18B 0.977(17) . ?
C19 H19A 1.008(18) . ?
C19 H19B 0.979(18) . ?
C19 C20 1.526(2) . ?
C20 H20A 0.98(2) . ?
C20 H20B 1.06(2) . ?
C20 C21 1.521(3) . ?
C21 H21A 1.09(2) . ?
C21 H21B 1.02(3) . ?
C21 C22 1.482(5) . ?
C22 H22A 0.97(4) . ?
C22 H22B 1.08(3) . ?
C22 H22C 1.09(4) . ?

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
C13 O2 C18 104.55(11) . . ?
C14 O3 C18 104.94(11) . . ?
C2 C1 H1 136.3(11) . . ?
C2 C1 C7 94.95(14) . . ?
C7 C1 H1 128.7(11) . . ?
C1 C2 H2 135.4(12) . . ?
C1 C2 C3 95.08(13) . . ?
C3 C2 H2 129.6(12) . . ?
C2 C3 H3 115.0(10) . . ?
C2 C3 C7 84.89(12) . . ?
C4 C3 C2 117.31(13) . . ?
C4 C3 H3 115.0(10) . . ?
C4 C3 C7 103.74(12) . . ?
C7 C3 H3 116.8(11) . . ?
C3 C4 H4 123.5(11) . . ?
C5 C4 C3 112.94(14) . . ?
C5 C4 H4 123.5(11) . . ?
C4 C5 H5 126.2(11) . . ?
C4 C5 C6 113.66(14) . . ?
C6 C5 H5 120.1(11) . . ?
C5 C6 C7 103.38(11) . . ?
C5 C6 C19 112.92(12) . . ?
C10 C6 C5 113.04(11) . . ?
C10 C6 C7 100.76(10) . . ?
C10 C6 C19 111.59(11) . . ?
C19 C6 C7 114.32(11) . . ?
C1 C7 C3 85.05(12) . . ?
C1 C7 C6 121.14(12) . . ?
C1 C7 C8 119.95(12) . . ?
C6 C7 C3 105.94(11) . . ?
C8 C7 C3 115.26(12) . . ?
C8 C7 C6 107.01(10) . . ?
O1 C8 C7 125.16(12) . . ?
O1 C8 C9 128.86(13) . . ?
C9 C8 C7 105.94(11) . . ?
C8 C9 C17 137.87(12) . . ?
C10 C9 C8 110.60(12) . . ?
C10 C9 C17 111.49(12) . . ?
C9 C10 C6 114.16(12) . . ?
C9 C10 C11 110.12(12) . . ?
C11 C10 C6 135.71(12) . . ?
C12 C11 C10 131.19(12) . . ?
C12 C11 C16 122.10(12) . . ?
C16 C11 C10 106.66(11) . . ?
C11 C12 H12 122.5(9) . . ?
C13 C12 C11 115.09(12) . . ?
C13 C12 H12 122.4(9) . . ?
O2 C13 C14 109.71(12) . . ?
C12 C13 O2 127.47(13) . . ?
C12 C13 C14 122.78(13) . . ?
O3 C14 C13 109.19(12) . . ?
C15 C14 O3 127.51(13) . . ?
C15 C14 C13 123.28(12) . . ?
C14 C15 H15 121.9(9) . . ?
C14 C15 C16 115.25(12) . . ?
C16 C15 H15 122.8(9) . . ?
C11 C16 C17 110.12(11) . . ?
C15 C16 C11 121.46(12) . . ?
C15 C16 C17 128.38(12) . . ?
C9 C17 C16 101.57(11) . . ?
C9 C17 H17A 113.7(9) . . ?
C9 C17 H17B 112.0(9) . . ?
C16 C17 H17A 111.6(9) . . ?
C16 C17 H17B 112.8(9) . . ?
H17A C17 H17B 105.4(13) . . ?
O2 C18 H18A 109.5(10) . . ?
O2 C18 H18B 106.8(10) . . ?
O3 C18 O2 106.83(11) . . ?
O3 C18 H18A 109.0(9) . . ?
O3 C18 H18B 111.6(10) . . ?
H18A C18 H18B 112.9(14) . . ?
C6 C19 H19A 108.0(10) . . ?
C6 C19 H19B 107.7(10) . . ?
H19A C19 H19B 105.9(14) . . ?
C20 C19 C6 113.68(13) . . ?
C20 C19 H19A 110.5(10) . . ?
C20 C19 H19B 110.6(10) . . ?
C19 C20 H20A 107.5(11) . . ?
C19 C20 H20B 109.1(11) . . ?
H20A C20 H20B 106.5(15) . . ?
C21 C20 C19 113.99(16) . . ?
C21 C20 H20A 110.7(11) . . ?
C21 C20 H20B 108.8(11) . . ?
C20 C21 H21A 115.5(12) . . ?
C20 C21 H21B 109.9(15) . . ?
H21A C21 H21B 107.3(19) . . ?
C22 C21 C20 113.8(2) . . ?
C22 C21 H21A 103.9(12) . . ?
C22 C21 H21B 105.8(16) . . ?
C21 C22 H22A 107(2) . . ?
C21 C22 H22B 108.7(16) . . ?
C21 C22 H22C 112.4(18) . . ?
H22A C22 H22B 110(3) . . ?
H22A C22 H22C 115(3) . . ?
H22B C22 H22C 103(3) . . ?

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 C8 C9 C10 -178.25(14) . . . . ?
O1 C8 C9 C17 4.4(3) . . . . ?
O2 C13 C14 O3 0.20(16) . . . . ?
O2 C13 C14 C15 179.04(13) . . . . ?
O3 C14 C15 C16 178.94(13) . . . . ?
C1 C2 C3 C4 -101.61(16) . . . . ?
C1 C2 C3 C7 1.23(13) . . . . ?
C1 C7 C8 O1 28.5(2) . . . . ?
C1 C7 C8 C9 -153.45(14) . . . . ?
C2 C1 C7 C3 1.23(13) . . . . ?
C2 C1 C7 C6 106.88(15) . . . . ?
C2 C1 C7 C8 -115.17(15) . . . . ?
C2 C3 C4 C5 94.04(18) . . . . ?
C2 C3 C7 C1 -1.07(11) . . . . ?
C2 C3 C7 C6 -122.07(12) . . . . ?
C2 C3 C7 C8 119.82(13) . . . . ?
C3 C4 C5 C6 1.06(19) . . . . ?
C3 C7 C8 O1 -70.77(18) . . . . ?
C3 C7 C8 C9 107.24(13) . . . . ?
C4 C3 C7 C1 115.83(13) . . . . ?
C4 C3 C7 C6 -5.18(15) . . . . ?
C4 C3 C7 C8 -123.29(13) . . . . ?
C4 C5 C6 C7 -4.38(16) . . . . ?
C4 C5 C6 C10 103.66(15) . . . . ?
C4 C5 C6 C19 -128.46(14) . . . . ?
C5 C6 C7 C1 -88.24(15) . . . . ?
C5 C6 C7 C3 5.65(14) . . . . ?
C5 C6 C7 C8 129.12(12) . . . . ?
C5 C6 C10 C9 -120.23(13) . . . . ?
C5 C6 C10 C11 60.9(2) . . . . ?
C5 C6 C19 C20 177.57(13) . . . . ?
C6 C7 C8 O1 171.72(13) . . . . ?
C6 C7 C8 C9 -10.28(14) . . . . ?
C6 C10 C11 C12 -5.2(3) . . . . ?
C6 C10 C11 C16 177.33(14) . . . . ?
C6 C19 C20 C21 -168.16(17) . . . . ?
C7 C1 C2 C3 -1.28(13) . . . . ?
C7 C3 C4 C5 2.72(17) . . . . ?
C7 C6 C10 C9 -10.55(15) . . . . ?
C7 C6 C10 C11 170.60(15) . . . . ?
C7 C6 C19 C20 59.74(17) . . . . ?
C7 C8 C9 C10 3.85(15) . . . . ?
C7 C8 C9 C17 -173.55(16) . . . . ?
C8 C9 C10 C6 4.60(16) . . . . ?
C8 C9 C10 C11 -176.26(11) . . . . ?
C8 C9 C17 C16 176.02(16) . . . . ?
C9 C10 C11 C12 175.88(14) . . . . ?
C9 C10 C11 C16 -1.55(15) . . . . ?
C10 C6 C7 C1 154.71(13) . . . . ?
C10 C6 C7 C3 -111.40(12) . . . . ?
C10 C6 C7 C8 12.07(13) . . . . ?
C10 C6 C19 C20 -53.79(17) . . . . ?
C10 C9 C17 C16 -1.37(15) . . . . ?
C10 C11 C12 C13 -176.79(13) . . . . ?
C10 C11 C16 C15 178.71(12) . . . . ?
C10 C11 C16 C17 0.64(15) . . . . ?
C11 C12 C13 O2 -178.94(13) . . . . ?
C11 C12 C13 C14 -1.3(2) . . . . ?
C11 C16 C17 C9 0.38(14) . . . . ?
C12 C11 C16 C15 1.0(2) . . . . ?
C12 C11 C16 C17 -177.08(12) . . . . ?
C12 C13 C14 O3 -177.83(13) . . . . ?
C12 C13 C14 C15 1.0(2) . . . . ?
C13 O2 C18 O3 -21.10(15) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 O3 C18 O2 21.30(15) . . . . ?
C14 C15 C16 C11 -1.3(2) . . . . ?
C14 C15 C16 C17 176.42(13) . . . . ?
C15 C16 C17 C9 -177.52(13) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
C17 C9 C10 C6 -177.28(11) . . . . ?
C17 C9 C10 C11 1.87(16) . . . . ?
C18 O2 C13 C12 -169.04(15) . . . . ?
C18 O2 C13 C14 13.03(15) . . . . ?
C18 O3 C14 C13 -13.40(15) . . . . ?
C18 O3 C14 C15 167.83(14) . . . . ?
C19 C6 C7 C1 34.91(18) . . . . ?
C19 C6 C7 C3 128.80(12) . . . . ?
C19 C6 C7 C8 -107.73(13) . . . . ?
C19 C6 C10 C9 111.19(13) . . . . ?
C19 C6 C10 C11 -67.65(19) . . . . ?
C19 C20 C21 C22 -67.7(3) . . . . ?

####################################################################### 
# 
# 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_13a
_database_code_depnum_ccdc_archive 'CCDC 2072296'
loop_
_audit_author_name
_audit_author_address
'Andrei S. Batsanov'
;Durham University
United Kingdom
;
_audit_update_record             
;
2021-03-22 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;

_audit_creation_date             2021-02-18
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6270)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        
; Rac-4c-Butyl-4c,11-dihydro-10H-azuleno[1',2':1,2]indeno[5,6-d][1,3]dioxol-10-one 
;
_chemical_formula_moiety         'C22 H20 O3'
_chemical_formula_sum            'C22 H20 O3'
_chemical_formula_weight         332.38
_chemical_melting_point          'decomposition above 393 K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8756(2)
_cell_length_b                   8.8807(2)
_cell_length_c                   14.0693(3)
_cell_angle_alpha                84.7360(10)
_cell_angle_beta                 86.7728(11)
_cell_angle_gamma                81.7271(10)
_cell_volume                     845.73(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9109
_cell_measurement_temperature    120
_cell_measurement_theta_max      35.61
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
wR2(int) was 0.1053 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.9237.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.0670
0.00 -1.00 0.00 0.0950
0.00 0.00 -1.00 0.0790
0.00 -1.00 1.00 0.1170
0.00 0.00 1.00 0.1180
0.00 1.00 1.00 0.1120
-1.00 1.00 1.00 0.1070
1.00 -1.00 -1.00 0.1540
1.00 1.00 0.00 0.2340
1.00 -2.00 2.00 0.1260
2.00 -1.00 2.00 0.1630
-1.00 -1.00 -2.00 0.2280

_exptl_crystal_size_max          0.508
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 3 runs of 175 narrow-frame ω-scans (scan 
width 1°, 3s exposure), every run at a different φ angle.
One run of 358 φ-scans (scan width 1°, 1s exposure) were used for 
scaling overflowing intensities. Crystal to detector distance 3.50 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17755
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.498
_diffrn_reflns_theta_min         2.326
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker PHOTON III C14 MM CPAD'
_diffrn_detector_area_resol_mean 54.4
_diffrn_detector_type            'CPA sensor'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω- and φ-scan'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\mS 3.0 microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4807
_reflns_number_total             6082
_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_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.40A (Bruker AXS, 2019)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT v8.40A (Bruker AXS, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015a)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         6082
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.040
_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)+(0.0735P)²+0.2695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1486
_refine_special_details          ?

_atom_sites_solution_hydrogens   difmap
_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 0.30558(14) 0.07624(10) 0.54847(7) 0.0256(2) Uani 1 1 d . . . . .
O2 O 0.12193(13) 0.17397(10) 0.67768(7) 0.02261(19) Uani 1 1 d . . . . .
O3 O 0.99963(13) 0.74245(10) 0.61889(6) 0.02178(19) Uani 1 1 d . . . . .
C1 C 0.55788(17) 0.24724(13) 0.54017(9) 0.0181(2) Uani 1 1 d . . . . .
H1 H 0.635(2) 0.2067(18) 0.4825(11) 0.017(4) Uiso 1 1 d . . . . .
C2 C 0.39027(17) 0.19221(13) 0.57884(9) 0.0184(2) Uani 1 1 d . . . . .
C3 C 0.28037(17) 0.25166(13) 0.65663(8) 0.0179(2) Uani 1 1 d . . . . .
C4 C 0.33070(17) 0.36998(13) 0.70223(8) 0.0169(2) Uani 1 1 d . . . . .
H4 H 0.254(2) 0.4086(19) 0.7589(12) 0.022(4) Uiso 1 1 d . . . . .
C5 C 0.50105(16) 0.42828(12) 0.66391(8) 0.01488(19) Uani 1 1 d . . . . .
C6 C 0.59555(16) 0.55394(12) 0.68932(8) 0.01476(19) Uani 1 1 d . . . . .
C7 C 0.56978(16) 0.65894(13) 0.76870(8) 0.0153(2) Uani 1 1 d . . . . .
C8 C 0.36989(17) 0.75486(14) 0.77206(8) 0.0186(2) Uani 1 1 d . . . . .
H8 H 0.263(3) 0.721(2) 0.7358(13) 0.030(4) Uiso 1 1 d . . . . .
C9 C 0.32193(19) 0.87783(15) 0.82239(9) 0.0232(2) Uani 1 1 d . . . . .
H9 H 0.178(3) 0.924(2) 0.8241(13) 0.037(5) Uiso 1 1 d . . . . .
C10 C 0.4515(2) 0.95525(15) 0.87251(10) 0.0257(3) Uani 1 1 d . . . . .
H10 H 0.384(3) 1.020(2) 0.9243(14) 0.037(5) Uiso 1 1 d . . . . .
C11 C 0.6448(2) 0.96004(15) 0.85227(10) 0.0256(3) Uani 1 1 d . . . . .
H11 H 0.714(3) 1.032(2) 0.8833(14) 0.036(5) Uiso 1 1 d . . . . .
C12 C 0.76222(19) 0.88535(15) 0.77756(9) 0.0229(2) Uani 1 1 d . . . . .
H12 H 0.878(3) 0.936(2) 0.7503(13) 0.034(5) Uiso 1 1 d . . . . .
C13 C 0.72787(17) 0.75962(13) 0.73807(8) 0.0165(2) Uani 1 1 d . . . . .
C14 C 0.84878(17) 0.69703(13) 0.65447(8) 0.0163(2) Uani 1 1 d . . . . .
C15 C 0.75230(16) 0.57293(12) 0.62864(8) 0.0151(2) Uani 1 1 d . . . . .
C16 C 0.78136(17) 0.45689(13) 0.55702(8) 0.0159(2) Uani 1 1 d . . . . .
H16A H 0.907(3) 0.390(2) 0.5623(12) 0.026(4) Uiso 1 1 d . . . . .
H16B H 0.780(2) 0.5006(19) 0.4912(12) 0.025(4) Uiso 1 1 d . . . . .
C17 C 0.61100(16) 0.36866(12) 0.58447(8) 0.0152(2) Uani 1 1 d . . . . .
C18 C 0.1178(2) 0.08245(15) 0.59899(10) 0.0246(3) Uani 1 1 d . . . . .
H18A H 0.019(3) 0.136(2) 0.5539(12) 0.025(4) Uiso 1 1 d . . . . .
H18B H 0.097(3) -0.020(2) 0.6235(14) 0.035(5) Uiso 1 1 d . . . . .
C19 C 0.61039(17) 0.56334(14) 0.86552(8) 0.0175(2) Uani 1 1 d . . . . .
H19A H 0.502(2) 0.5007(18) 0.8776(11) 0.017(4) Uiso 1 1 d . . . . .
H19B H 0.601(2) 0.6313(18) 0.9176(11) 0.019(4) Uiso 1 1 d . . . . .
C20 C 0.80685(18) 0.45889(15) 0.86667(9) 0.0211(2) Uani 1 1 d . . . . .
H20A H 0.818(3) 0.393(2) 0.8103(14) 0.039(5) Uiso 1 1 d . . . . .
H20B H 0.919(3) 0.525(2) 0.8598(12) 0.030(4) Uiso 1 1 d . . . . .
C21 C 0.8338(2) 0.35524(16) 0.95873(9) 0.0255(3) Uani 1 1 d . . . . .
H21A H 0.716(3) 0.294(2) 0.9695(13) 0.034(5) Uiso 1 1 d . . . . .
H21B H 0.831(3) 0.417(2) 1.0128(14) 0.035(5) Uiso 1 1 d . . . . .
C22 C 1.0251(2) 0.24501(19) 0.95653(13) 0.0358(3) Uani 1 1 d . . . . .
H22A H 1.036(3) 0.185(2) 0.8998(15) 0.043(5) Uiso 1 1 d . . . . .
H22B H 1.143(3) 0.299(2) 0.9447(15) 0.048(6) Uiso 1 1 d . . . . .
H22C H 1.037(3) 0.176(3) 1.0148(16) 0.052(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3652(13) . ?
O1 C18 1.4350(16) . ?
O2 C3 1.3758(14) . ?
O2 C18 1.4363(16) . ?
O3 C14 1.2304(14) . ?
C1 H1 1.009(16) . ?
C1 C2 1.3804(16) . ?
C1 C17 1.3953(15) . ?
C2 C3 1.3948(17) . ?
C3 C4 1.3743(16) . ?
C4 H4 0.993(16) . ?
C4 C5 1.4081(15) . ?
C5 C6 1.4503(15) . ?
C5 C17 1.4140(15) . ?
C6 C7 1.5065(15) . ?
C6 C15 1.3569(15) . ?
C7 C8 1.5099(16) . ?
C7 C13 1.5241(16) . ?
C7 C19 1.5546(16) . ?
C8 H8 1.015(18) . ?
C8 C9 1.3470(17) . ?
C9 H9 1.014(19) . ?
C9 C10 1.4493(19) . ?
C10 H10 1.02(2) . ?
C10 C11 1.349(2) . ?
C11 H11 1.00(2) . ?
C11 C12 1.4403(18) . ?
C12 H12 1.010(19) . ?
C12 C13 1.3474(16) . ?
C13 C14 1.5035(16) . ?
C14 C15 1.4484(15) . ?
C15 C16 1.4920(15) . ?
C16 H16A 0.977(17) . ?
C16 H16B 0.970(17) . ?
C16 C17 1.5141(15) . ?
C18 H18A 0.997(17) . ?
C18 H18B 0.972(19) . ?
C19 H19A 0.989(16) . ?
C19 H19B 0.984(16) . ?
C19 C20 1.5246(17) . ?
C20 H20A 1.02(2) . ?
C20 H20B 1.025(18) . ?
C20 C21 1.5226(18) . ?
C21 H21A 1.035(19) . ?
C21 H21B 0.977(19) . ?
C21 C22 1.523(2) . ?
C22 H22A 0.99(2) . ?
C22 H22B 1.00(2) . ?
C22 H22C 0.98(2) . ?

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
C2 O1 C18 105.29(9) . . ?
C3 O2 C18 104.95(9) . . ?
C2 C1 H1 123.4(9) . . ?
C2 C1 C17 115.08(10) . . ?
C17 C1 H1 121.5(9) . . ?
O1 C2 C1 126.89(11) . . ?
O1 C2 C3 109.81(10) . . ?
C1 C2 C3 123.29(10) . . ?
O2 C3 C2 109.50(10) . . ?
C4 C3 O2 127.71(11) . . ?
C4 C3 C2 122.79(10) . . ?
C3 C4 H4 121.8(10) . . ?
C3 C4 C5 114.96(10) . . ?
C5 C4 H4 123.2(10) . . ?
C4 C5 C6 131.31(10) . . ?
C4 C5 C17 122.08(10) . . ?
C17 C5 C6 106.57(9) . . ?
C5 C6 C7 135.78(10) . . ?
C15 C6 C5 110.24(10) . . ?
C15 C6 C7 113.84(10) . . ?
C6 C7 C8 113.01(9) . . ?
C6 C7 C13 100.30(9) . . ?
C6 C7 C19 109.27(9) . . ?
C8 C7 C13 110.07(9) . . ?
C8 C7 C19 111.03(9) . . ?
C13 C7 C19 112.78(9) . . ?
C7 C8 H8 117.1(10) . . ?
C9 C8 C7 124.95(11) . . ?
C9 C8 H8 117.9(10) . . ?
C8 C9 H9 116.3(11) . . ?
C8 C9 C10 127.98(12) . . ?
C10 C9 H9 115.7(11) . . ?
C9 C10 H10 115.2(11) . . ?
C11 C10 C9 126.85(12) . . ?
C11 C10 H10 117.7(11) . . ?
C10 C11 H11 119.8(11) . . ?
C10 C11 C12 126.06(12) . . ?
C12 C11 H11 113.4(11) . . ?
C11 C12 H12 115.8(11) . . ?
C13 C12 C11 126.59(12) . . ?
C13 C12 H12 117.5(11) . . ?
C12 C13 C7 127.51(11) . . ?
C12 C13 C14 122.94(11) . . ?
C14 C13 C7 109.55(9) . . ?
O3 C14 C13 125.80(10) . . ?
O3 C14 C15 128.89(10) . . ?
C15 C14 C13 105.29(9) . . ?
C6 C15 C14 110.46(10) . . ?
C6 C15 C16 111.48(10) . . ?
C14 C15 C16 138.00(10) . . ?
C15 C16 H16A 112.7(10) . . ?
C15 C16 H16B 113.8(10) . . ?
C15 C16 C17 101.29(9) . . ?
H16A C16 H16B 105.2(14) . . ?
C17 C16 H16A 110.9(10) . . ?
C17 C16 H16B 113.1(10) . . ?
C1 C17 C5 121.79(10) . . ?
C1 C17 C16 127.79(10) . . ?
C5 C17 C16 110.41(9) . . ?
O1 C18 O2 107.60(10) . . ?
O1 C18 H18A 106.6(10) . . ?
O1 C18 H18B 109.4(11) . . ?
O2 C18 H18A 108.6(10) . . ?
O2 C18 H18B 109.2(11) . . ?
H18A C18 H18B 115.2(15) . . ?
C7 C19 H19A 106.1(9) . . ?
C7 C19 H19B 110.0(9) . . ?
H19A C19 H19B 106.7(13) . . ?
C20 C19 C7 114.18(9) . . ?
C20 C19 H19A 109.2(9) . . ?
C20 C19 H19B 110.2(9) . . ?
C19 C20 H20A 109.4(11) . . ?
C19 C20 H20B 108.9(10) . . ?
H20A C20 H20B 108.9(15) . . ?
C21 C20 C19 113.03(10) . . ?
C21 C20 H20A 108.8(11) . . ?
C21 C20 H20B 107.7(10) . . ?
C20 C21 H21A 108.8(11) . . ?
C20 C21 H21B 109.6(11) . . ?
C20 C21 C22 112.46(12) . . ?
H21A C21 H21B 107.0(15) . . ?
C22 C21 H21A 109.3(11) . . ?
C22 C21 H21B 109.6(11) . . ?
C21 C22 H22A 111.1(12) . . ?
C21 C22 H22B 112.6(13) . . ?
C21 C22 H22C 111.4(13) . . ?
H22A C22 H22B 100.4(17) . . ?
H22A C22 H22C 109.9(17) . . ?
H22B C22 H22C 110.9(17) . . ?

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 C2 C3 O2 0.04(14) . . . . ?
O1 C2 C3 C4 -179.99(11) . . . . ?
O2 C3 C4 C5 -179.40(11) . . . . ?
O3 C14 C15 C6 176.34(12) . . . . ?
O3 C14 C15 C16 -0.5(2) . . . . ?
C1 C2 C3 O2 179.48(11) . . . . ?
C1 C2 C3 C4 -0.55(19) . . . . ?
C2 O1 C18 O2 -16.44(13) . . . . ?
C2 C1 C17 C5 0.81(17) . . . . ?
C2 C1 C17 C16 -177.69(11) . . . . ?
C2 C3 C4 C5 0.64(17) . . . . ?
C3 O2 C18 O1 16.40(13) . . . . ?
C3 C4 C5 C6 177.44(11) . . . . ?
C3 C4 C5 C17 -0.02(17) . . . . ?
C4 C5 C6 C7 8.0(2) . . . . ?
C4 C5 C6 C15 -176.81(12) . . . . ?
C4 C5 C17 C1 -0.73(17) . . . . ?
C4 C5 C17 C16 178.00(10) . . . . ?
C5 C6 C7 C8 -61.40(16) . . . . ?
C5 C6 C7 C13 -178.53(12) . . . . ?
C5 C6 C7 C19 62.75(16) . . . . ?
C5 C6 C15 C14 -179.25(9) . . . . ?
C5 C6 C15 C16 -1.53(13) . . . . ?
C6 C5 C17 C1 -178.74(10) . . . . ?
C6 C5 C17 C16 -0.01(12) . . . . ?
C6 C7 C8 C9 -166.02(12) . . . . ?
C6 C7 C13 C12 173.25(12) . . . . ?
C6 C7 C13 C14 -7.39(11) . . . . ?
C6 C7 C19 C20 52.62(13) . . . . ?
C6 C15 C16 C17 1.42(12) . . . . ?
C7 C6 C15 C14 -2.91(14) . . . . ?
C7 C6 C15 C16 174.81(9) . . . . ?
C7 C8 C9 C10 8.6(2) . . . . ?
C7 C13 C14 O3 -172.29(11) . . . . ?
C7 C13 C14 C15 6.22(12) . . . . ?
C7 C19 C20 C21 -174.25(11) . . . . ?
C8 C7 C13 C12 53.96(15) . . . . ?
C8 C7 C13 C14 -126.68(10) . . . . ?
C8 C7 C19 C20 177.92(10) . . . . ?
C8 C9 C10 C11 26.6(2) . . . . ?
C9 C10 C11 C12 -1.6(2) . . . . ?
C10 C11 C12 C13 -25.3(2) . . . . ?
C11 C12 C13 C7 -6.1(2) . . . . ?
C11 C12 C13 C14 174.60(12) . . . . ?
C12 C13 C14 O3 7.10(19) . . . . ?
C12 C13 C14 C15 -174.38(11) . . . . ?
C13 C7 C8 C9 -54.81(15) . . . . ?
C13 C7 C19 C20 -58.01(13) . . . . ?
C13 C14 C15 C6 -2.11(13) . . . . ?
C13 C14 C15 C16 -178.94(13) . . . . ?
C14 C15 C16 C17 178.23(13) . . . . ?
C15 C6 C7 C8 123.52(11) . . . . ?
C15 C6 C7 C13 6.39(12) . . . . ?
C15 C6 C7 C19 -112.33(11) . . . . ?
C15 C16 C17 C1 177.83(11) . . . . ?
C15 C16 C17 C5 -0.81(12) . . . . ?
C17 C1 C2 O1 179.13(11) . . . . ?
C17 C1 C2 C3 -0.20(18) . . . . ?
C17 C5 C6 C7 -174.26(12) . . . . ?
C17 C5 C6 C15 0.94(13) . . . . ?
C18 O1 C2 C1 -169.21(12) . . . . ?
C18 O1 C2 C3 10.19(14) . . . . ?
C18 O2 C3 C2 -10.23(13) . . . . ?
C18 O2 C3 C4 169.80(12) . . . . ?
C19 C7 C8 C9 70.80(15) . . . . ?
C19 C7 C13 C12 -70.64(15) . . . . ?
C19 C7 C13 C14 108.72(10) . . . . ?
C19 C20 C21 C22 176.58(12) . . . . ?


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, ethyl acetate'
