# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1510311'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2017-01-19 downloaded from the CCDC.
;
_audit_creation_date             2016-10-17
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H13 Cl O3'
_chemical_formula_moiety         'C18 H13 Cl O3'
_chemical_formula_weight         312.75
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        I2
_space_group_name_Hall           'I 2y'
_space_group_IT_number           5
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,1/2+Z
4 1/2-X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   12.181(3)
_cell_length_b                   4.9624(11)
_cell_length_c                   48.446(13)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.245(9)
_cell_angle_gamma                90.0000
_cell_volume                     2927.7(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    930
_cell_measurement_theta_min      40.30
_cell_measurement_theta_max      68.30
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296.00
_exptl_absorpt_coefficient_mu    2.400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.976

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            18439
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_theta_max         68.294
_diffrn_reflns_theta_min         1.824
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_limit_l_max       58
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5104
_reflns_number_gt                3704
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     0.926
_reflns_Friedel_fraction_full    0.940

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1142
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5104
_refine_ls_number_parameters     397
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0678P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(12)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.85073(13) 1.2016(3) 0.50457(2) 0.0695(4) Uani 1 1 d . . . . .
Cl21 Cl 0.31526(12) 1.3056(3) 0.72773(2) 0.0607(4) Uani 1 1 d . . . . .
O1 O 0.9174(3) 0.5084(8) 0.62110(6) 0.0590(10) Uani 1 1 d . . . . .
O2 O 0.9961(3) 0.2142(9) 0.64916(7) 0.0627(10) Uani 1 1 d . . . . .
O10 O 0.6972(3) 0.1862(8) 0.69084(6) 0.0557(9) Uani 1 1 d . . . . .
O21 O 0.4162(3) 0.3578(7) 0.63488(5) 0.0508(9) Uani 1 1 d . . . . .
O22 O 0.5216(3) 0.0594(8) 0.61511(6) 0.0610(10) Uani 1 1 d . . . . .
O30 O 0.1700(3) 0.4257(7) 0.56242(6) 0.0561(9) Uani 1 1 d . . . . .
C2 C 0.9331(4) 0.3979(11) 0.64702(9) 0.0490(12) Uani 1 1 d . . . . .
C3 C 0.8700(4) 0.5333(11) 0.66992(9) 0.0481(12) Uani 1 1 d . . . . .
H3 H 0.9013 0.7174 0.6730 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8815(4) 0.3758(9) 0.69661(8) 0.0411(11) Uani 1 1 d . . . . .
C5 C 0.9755(4) 0.3940(10) 0.71335(9) 0.0502(12) Uani 1 1 d . . . . .
H5 H 1.0328 0.5133 0.7084 0.060 Uiso 1 1 calc R U . . .
C6 C 0.9866(4) 0.2409(11) 0.73708(9) 0.0554(14) Uani 1 1 d . . . . .
H6 H 1.0512 0.2553 0.7483 0.067 Uiso 1 1 calc R U . . .
C7 C 0.9032(5) 0.0660(12) 0.74444(10) 0.0603(15) Uani 1 1 d . . . . .
H7 H 0.9116 -0.0434 0.7604 0.072 Uiso 1 1 calc R U . . .
C8 C 0.8083(5) 0.0513(11) 0.72857(9) 0.0565(14) Uani 1 1 d . . . . .
H8 H 0.7503 -0.0643 0.7339 0.068 Uiso 1 1 calc R U . . .
C9 C 0.7975(4) 0.2064(10) 0.70469(8) 0.0444(11) Uani 1 1 d . . . . .
C11 C 0.6931(4) 0.2882(11) 0.66314(9) 0.0524(12) Uani 1 1 d . . . . .
H11A H 0.6155 0.3044 0.6569 0.063 Uiso 1 1 calc R U . . .
H11B H 0.7299 0.1592 0.6508 0.063 Uiso 1 1 calc R U . . .
C12 C 0.7487(4) 0.5623(10) 0.66112(9) 0.0475(12) Uani 1 1 d . . . . .
H12 H 0.7123 0.6903 0.6740 0.057 Uiso 1 1 calc R U . . .
C13 C 0.7408(4) 0.6739(11) 0.63238(9) 0.0512(12) Uani 1 1 d . . . . .
H13 H 0.6742 0.7577 0.6265 0.061 Uiso 1 1 calc R U . . .
C14 C 0.8223(4) 0.6609(11) 0.61485(9) 0.0514(12) Uani 1 1 d . . . . .
C15 C 0.8304(4) 0.7855(11) 0.58733(9) 0.0504(12) Uani 1 1 d . . . . .
C16 C 0.9124(4) 0.7236(12) 0.56904(10) 0.0623(15) Uani 1 1 d . . . . .
H16 H 0.9658 0.5920 0.5741 0.075 Uiso 1 1 calc R U . . .
C17 C 0.9186(5) 0.8470(13) 0.54386(10) 0.0638(15) Uani 1 1 d . . . . .
H17 H 0.9754 0.7997 0.5316 0.077 Uiso 1 1 calc R U . . .
C18 C 0.8433(5) 1.0375(12) 0.53635(9) 0.0554(13) Uani 1 1 d . . . . .
C19 C 0.7605(5) 1.1069(14) 0.55384(11) 0.078(2) Uani 1 1 d . . . . .
H19 H 0.7075 1.2380 0.5484 0.094 Uiso 1 1 calc R U . . .
C20 C 0.7548(5) 0.9850(14) 0.57938(12) 0.080(2) Uani 1 1 d . . . . .
H20 H 0.6989 1.0370 0.5917 0.096 Uiso 1 1 calc R U . . .
C22 C 0.4353(4) 0.1777(11) 0.61412(8) 0.0473(12) Uani 1 1 d . . . . .
C23 C 0.3509(4) 0.1506(10) 0.59144(8) 0.0443(12) Uani 1 1 d . . . . .
H23 H 0.3604 -0.0293 0.5825 0.053 Uiso 1 1 calc R U . . .
C24 C 0.3672(4) 0.3673(10) 0.56975(8) 0.0447(12) Uani 1 1 d . . . . .
C25 C 0.4715(5) 0.4521(12) 0.56220(10) 0.0598(15) Uani 1 1 d . . . . .
H25 H 0.5342 0.3772 0.5714 0.072 Uiso 1 1 calc R U . . .
C26 C 0.4862(6) 0.6423(14) 0.54173(11) 0.0778(19) Uani 1 1 d . . . . .
H26 H 0.5580 0.6949 0.5367 0.093 Uiso 1 1 calc R U . . .
C27 C 0.3942(6) 0.7559(13) 0.52861(10) 0.0712(18) Uani 1 1 d . . . . .
H27 H 0.4031 0.8887 0.5147 0.085 Uiso 1 1 calc R U . . .
C28 C 0.2918(5) 0.6761(12) 0.53579(9) 0.0607(15) Uani 1 1 d . . . . .
H28 H 0.2295 0.7529 0.5266 0.073 Uiso 1 1 calc R U . . .
C29 C 0.2768(4) 0.4853(10) 0.55618(8) 0.0480(12) Uani 1 1 d . . . . .
C31 C 0.1529(4) 0.1879(12) 0.57867(10) 0.0533(12) Uani 1 1 d . . . . .
H31A H 0.1594 0.0269 0.5668 0.064 Uiso 1 1 calc R U . . .
H31B H 0.0775 0.1911 0.5859 0.064 Uiso 1 1 calc R U . . .
C32 C 0.2346(4) 0.1660(11) 0.60261(9) 0.0455(11) Uani 1 1 d . . . . .
H32 H 0.2195 -0.0045 0.6128 0.055 Uiso 1 1 calc R U . . .
C33 C 0.2283(4) 0.3967(10) 0.62247(9) 0.0450(12) Uani 1 1 d . . . . .
H33 H 0.1601 0.4871 0.6243 0.054 Uiso 1 1 calc R U . . .
C34 C 0.3136(4) 0.4799(9) 0.63755(8) 0.0396(11) Uani 1 1 d . . . . .
C35 C 0.3154(4) 0.6870(10) 0.65946(8) 0.0397(10) Uani 1 1 d . . . . .
C36 C 0.4138(4) 0.7721(10) 0.67186(8) 0.0459(12) Uani 1 1 d . . . . .
H36 H 0.4813 0.6975 0.6660 0.055 Uiso 1 1 calc R U . . .
C37 C 0.4141(4) 0.9657(10) 0.69272(8) 0.0477(12) Uani 1 1 d . . . . .
H37 H 0.4815 1.0253 0.7009 0.057 Uiso 1 1 calc R U . . .
C38 C 0.3166(4) 1.0690(10) 0.70137(8) 0.0441(12) Uani 1 1 d . . . . .
C39 C 0.2180(4) 0.9881(11) 0.68943(9) 0.0501(13) Uani 1 1 d . . . . .
H39 H 0.1508 1.0622 0.6955 0.060 Uiso 1 1 calc R U . . .
C40 C 0.2182(4) 0.7987(11) 0.66861(8) 0.0482(12) Uani 1 1 d . . . . .
H40 H 0.1504 0.7434 0.6603 0.058 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Cl1 C18 1.746(5) . ?
Cl21 C38 1.735(4) . ?
O1 C2 1.380(6) . ?
O1 C14 1.411(6) . ?
O2 C2 1.195(6) . ?
O10 C9 1.384(5) . ?
O10 C11 1.434(5) . ?
O21 C22 1.369(5) . ?
O21 C34 1.397(5) . ?
O22 C22 1.204(5) . ?
O30 C29 1.373(6) . ?
O30 C31 1.437(6) . ?
C2 C3 1.519(7) . ?
C3 C4 1.515(6) . ?
C3 C12 1.536(7) . ?
C3 H3 1.0000 . ?
C4 C9 1.388(6) . ?
C4 C5 1.392(7) . ?
C5 C6 1.382(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.376(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(7) . ?
C8 H8 0.9500 . ?
C11 C12 1.524(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.499(6) . ?
C12 H12 1.0000 . ?
C13 C14 1.322(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.475(6) . ?
C15 C16 1.384(7) . ?
C15 C20 1.401(8) . ?
C16 C17 1.368(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.361(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(8) . ?
C19 C20 1.380(8) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C22 C23 1.495(6) . ?
C23 C24 1.519(6) . ?
C23 C32 1.529(7) . ?
C23 H23 1.0000 . ?
C24 C25 1.395(7) . ?
C24 C29 1.399(6) . ?
C25 C26 1.384(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.395(9) . ?
C26 H26 0.9500 . ?
C27 C28 1.362(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(7) . ?
C28 H28 0.9500 . ?
C31 C32 1.516(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.499(6) . ?
C32 H32 1.0000 . ?
C33 C34 1.323(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.477(6) . ?
C35 C40 1.388(6) . ?
C35 C36 1.395(6) . ?
C36 C37 1.394(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.368(7) . ?
C37 H37 0.9500 . ?
C38 C39 1.381(7) . ?
C39 C40 1.379(7) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?

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 C14 120.4(4) . . ?
C9 O10 C11 116.1(4) . . ?
C22 O21 C34 121.2(3) . . ?
C29 O30 C31 116.6(4) . . ?
O2 C2 O1 117.3(4) . . ?
O2 C2 C3 127.4(4) . . ?
O1 C2 C3 115.3(4) . . ?
C4 C3 C2 110.9(4) . . ?
C4 C3 C12 110.8(4) . . ?
C2 C3 C12 109.7(4) . . ?
C4 C3 H3 108.4 . . ?
C2 C3 H3 108.4 . . ?
C12 C3 H3 108.4 . . ?
C9 C4 C5 118.6(4) . . ?
C9 C4 C3 119.9(4) . . ?
C5 C4 C3 121.6(4) . . ?
C6 C5 C4 120.9(5) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.9(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.0(5) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.9(5) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
O10 C9 C4 123.8(4) . . ?
O10 C9 C8 115.4(4) . . ?
C4 C9 C8 120.8(4) . . ?
O10 C11 C12 111.6(4) . . ?
O10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
O10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 111.7(4) . . ?
C13 C12 C3 109.5(4) . . ?
C11 C12 C3 108.9(4) . . ?
C13 C12 H12 108.9 . . ?
C11 C12 H12 108.9 . . ?
C3 C12 H12 108.9 . . ?
C14 C13 C12 123.0(5) . . ?
C14 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
C13 C14 O1 120.8(4) . . ?
C13 C14 C15 128.8(5) . . ?
O1 C14 C15 110.4(4) . . ?
C16 C15 C20 117.4(5) . . ?
C16 C15 C14 123.3(5) . . ?
C20 C15 C14 119.2(4) . . ?
C17 C16 C15 121.7(5) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C18 C17 C16 119.9(5) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.6(5) . . ?
C17 C18 Cl1 120.8(4) . . ?
C19 C18 Cl1 118.6(4) . . ?
C18 C19 C20 119.6(5) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C15 120.7(5) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
O22 C22 O21 116.8(4) . . ?
O22 C22 C23 124.9(4) . . ?
O21 C22 C23 118.2(4) . . ?
C22 C23 C24 110.3(4) . . ?
C22 C23 C32 111.3(4) . . ?
C24 C23 C32 110.2(4) . . ?
C22 C23 H23 108.3 . . ?
C24 C23 H23 108.3 . . ?
C32 C23 H23 108.3 . . ?
C25 C24 C29 117.6(5) . . ?
C25 C24 C23 121.9(4) . . ?
C29 C24 C23 120.6(4) . . ?
C26 C25 C24 121.8(5) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C25 C26 C27 119.1(6) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C28 C27 C26 119.9(5) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C27 C28 C29 121.2(5) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
O30 C29 C28 116.4(5) . . ?
O30 C29 C24 123.1(4) . . ?
C28 C29 C24 120.5(5) . . ?
O30 C31 C32 112.2(4) . . ?
O30 C31 H31A 109.2 . . ?
C32 C31 H31A 109.2 . . ?
O30 C31 H31B 109.2 . . ?
C32 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
C33 C32 C31 113.2(4) . . ?
C33 C32 C23 109.0(4) . . ?
C31 C32 C23 109.3(4) . . ?
C33 C32 H32 108.4 . . ?
C31 C32 H32 108.4 . . ?
C23 C32 H32 108.4 . . ?
C34 C33 C32 122.9(4) . . ?
C34 C33 H33 118.6 . . ?
C32 C33 H33 118.6 . . ?
C33 C34 O21 120.4(4) . . ?
C33 C34 C35 127.8(4) . . ?
O21 C34 C35 111.7(4) . . ?
C40 C35 C36 118.2(4) . . ?
C40 C35 C34 120.5(4) . . ?
C36 C35 C34 121.3(4) . . ?
C37 C36 C35 120.6(4) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C38 C37 C36 119.5(4) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C37 C38 C39 121.0(4) . . ?
C37 C38 Cl21 120.1(4) . . ?
C39 C38 Cl21 118.9(4) . . ?
C40 C39 C38 119.3(4) . . ?
C40 C39 H39 120.3 . . ?
C38 C39 H39 120.3 . . ?
C39 C40 C35 121.4(4) . . ?
C39 C40 H40 119.3 . . ?
C35 C40 H40 119.3 . . ?

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
C14 O1 C2 O2 159.6(5) . . . . ?
C14 O1 C2 C3 -22.4(7) . . . . ?
O2 C2 C3 C4 -9.5(7) . . . . ?
O1 C2 C3 C4 172.8(4) . . . . ?
O2 C2 C3 C12 -132.3(6) . . . . ?
O1 C2 C3 C12 50.0(6) . . . . ?
C2 C3 C4 C9 -100.6(5) . . . . ?
C12 C3 C4 C9 21.6(6) . . . . ?
C2 C3 C4 C5 78.8(6) . . . . ?
C12 C3 C4 C5 -159.1(4) . . . . ?
C9 C4 C5 C6 1.9(7) . . . . ?
C3 C4 C5 C6 -177.4(4) . . . . ?
C4 C5 C6 C7 0.0(7) . . . . ?
C5 C6 C7 C8 -1.9(8) . . . . ?
C6 C7 C8 C9 1.8(8) . . . . ?
C11 O10 C9 C4 17.6(6) . . . . ?
C11 O10 C9 C8 -165.1(4) . . . . ?
C5 C4 C9 O10 175.2(4) . . . . ?
C3 C4 C9 O10 -5.5(7) . . . . ?
C5 C4 C9 C8 -2.0(7) . . . . ?
C3 C4 C9 C8 177.3(4) . . . . ?
C7 C8 C9 O10 -177.3(5) . . . . ?
C7 C8 C9 C4 0.2(7) . . . . ?
C9 O10 C11 C12 -45.5(6) . . . . ?
O10 C11 C12 C13 -177.9(4) . . . . ?
O10 C11 C12 C3 61.0(5) . . . . ?
C4 C3 C12 C13 -169.9(4) . . . . ?
C2 C3 C12 C13 -47.1(6) . . . . ?
C4 C3 C12 C11 -47.4(5) . . . . ?
C2 C3 C12 C11 75.4(5) . . . . ?
C11 C12 C13 C14 -100.2(6) . . . . ?
C3 C12 C13 C14 20.6(8) . . . . ?
C12 C13 C14 O1 8.4(9) . . . . ?
C12 C13 C14 C15 -172.9(5) . . . . ?
C2 O1 C14 C13 -8.2(8) . . . . ?
C2 O1 C14 C15 172.9(4) . . . . ?
C13 C14 C15 C16 -169.5(6) . . . . ?
O1 C14 C15 C16 9.3(8) . . . . ?
C13 C14 C15 C20 13.2(9) . . . . ?
O1 C14 C15 C20 -168.0(5) . . . . ?
C20 C15 C16 C17 -1.4(9) . . . . ?
C14 C15 C16 C17 -178.7(5) . . . . ?
C15 C16 C17 C18 0.5(10) . . . . ?
C16 C17 C18 C19 -0.2(10) . . . . ?
C16 C17 C18 Cl1 179.0(5) . . . . ?
C17 C18 C19 C20 1.0(10) . . . . ?
Cl1 C18 C19 C20 -178.3(5) . . . . ?
C18 C19 C20 C15 -2.0(11) . . . . ?
C16 C15 C20 C19 2.2(10) . . . . ?
C14 C15 C20 C19 179.6(6) . . . . ?
C34 O21 C22 O22 -171.9(4) . . . . ?
C34 O21 C22 C23 10.7(6) . . . . ?
O22 C22 C23 C24 -93.5(6) . . . . ?
O21 C22 C23 C24 83.7(5) . . . . ?
O22 C22 C23 C32 143.9(5) . . . . ?
O21 C22 C23 C32 -38.9(6) . . . . ?
C22 C23 C24 C25 37.3(6) . . . . ?
C32 C23 C24 C25 160.6(4) . . . . ?
C22 C23 C24 C29 -144.0(4) . . . . ?
C32 C23 C24 C29 -20.8(6) . . . . ?
C29 C24 C25 C26 -1.1(7) . . . . ?
C23 C24 C25 C26 177.6(5) . . . . ?
C24 C25 C26 C27 1.2(9) . . . . ?
C25 C26 C27 C28 -0.9(9) . . . . ?
C26 C27 C28 C29 0.7(8) . . . . ?
C31 O30 C29 C28 166.2(4) . . . . ?
C31 O30 C29 C24 -15.2(6) . . . . ?
C27 C28 C29 O30 178.0(4) . . . . ?
C27 C28 C29 C24 -0.7(8) . . . . ?
C25 C24 C29 O30 -177.7(4) . . . . ?
C23 C24 C29 O30 3.6(7) . . . . ?
C25 C24 C29 C28 0.9(7) . . . . ?
C23 C24 C29 C28 -177.8(4) . . . . ?
C29 O30 C31 C32 44.2(5) . . . . ?
O30 C31 C32 C33 60.9(5) . . . . ?
O30 C31 C32 C23 -60.9(5) . . . . ?
C22 C23 C32 C33 45.7(5) . . . . ?
C24 C23 C32 C33 -77.0(5) . . . . ?
C22 C23 C32 C31 170.0(4) . . . . ?
C24 C23 C32 C31 47.3(5) . . . . ?
C31 C32 C33 C34 -151.9(5) . . . . ?
C23 C32 C33 C34 -29.9(6) . . . . ?
C32 C33 C34 O21 1.9(7) . . . . ?
C32 C33 C34 C35 -174.1(4) . . . . ?
C22 O21 C34 C33 9.4(6) . . . . ?
C22 O21 C34 C35 -174.0(4) . . . . ?
C33 C34 C35 C40 7.4(7) . . . . ?
O21 C34 C35 C40 -168.9(4) . . . . ?
C33 C34 C35 C36 -173.8(4) . . . . ?
O21 C34 C35 C36 9.9(6) . . . . ?
C40 C35 C36 C37 -0.5(7) . . . . ?
C34 C35 C36 C37 -179.3(4) . . . . ?
C35 C36 C37 C38 1.2(7) . . . . ?
C36 C37 C38 C39 -1.1(7) . . . . ?
C36 C37 C38 Cl21 178.8(4) . . . . ?
C37 C38 C39 C40 0.5(7) . . . . ?
Cl21 C38 C39 C40 -179.5(4) . . . . ?
C38 C39 C40 C35 0.2(8) . . . . ?
C36 C35 C40 C39 -0.2(7) . . . . ?
C34 C35 C40 C39 178.6(4) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/hexane'
####################################################################### 
# 
# 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_27
_database_code_depnum_ccdc_archive 'CCDC 1510312'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2017-01-19 downloaded from the CCDC.
;
_audit_creation_date             2016-10-17
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H14 O4'
_chemical_formula_moiety         'C18 H14 O4'
_chemical_formula_weight         294.31
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.7005(16)
_cell_length_b                   8.8005(16)
_cell_length_c                   18.865(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1444.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1462
_cell_measurement_theta_min      18.60
_cell_measurement_theta_max      46.90
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616.00
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            13304
_diffrn_reflns_av_R_equivalents  0.0905
_diffrn_reflns_theta_max         68.201
_diffrn_reflns_theta_min         4.688
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2616
_reflns_number_gt                2097
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.989

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1296
_refine_ls_wR_factor_gt          0.1232
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2616
_refine_ls_number_parameters     200
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0742P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0052(10)
_refine_ls_abs_structure_details 
;
 Flack x determined using 726 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.00(18)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.8838(3) 0.3129(3) 1.03730(11) 0.0530(6) Uani 1 1 d . . . . .
O2 O 0.8874(4) 0.3982(3) 1.14851(12) 0.0636(7) Uani 1 1 d . . . . .
O10 O 0.8694(3) 0.7748(2) 0.97248(11) 0.0507(6) Uani 1 1 d . . . . .
O14 O 0.7245(3) 0.2493(3) 0.92292(13) 0.0656(7) Uani 1 1 d . . . . .
C2 C 0.9252(4) 0.4149(4) 1.08793(17) 0.0500(8) Uani 1 1 d . . . . .
C3 C 1.0191(4) 0.5410(4) 1.05483(15) 0.0442(8) Uani 1 1 d . . . . .
H3 H 1.1303 0.5180 1.0626 0.053 Uiso 1 1 calc R U . . .
C4 C 0.9867(3) 0.6972(4) 1.08334(15) 0.0414(7) Uani 1 1 d . . . . .
C5 C 1.0315(4) 0.7393(4) 1.15100(17) 0.0492(8) Uani 1 1 d . . . . .
H5 H 1.0752 0.6651 1.1815 0.059 Uiso 1 1 calc R U . . .
C6 C 1.0142(4) 0.8867(4) 1.17525(18) 0.0533(9) Uani 1 1 d . . . . .
H6 H 1.0456 0.9137 1.2218 0.064 Uiso 1 1 calc R U . . .
C7 C 0.9505(4) 0.9941(4) 1.13052(18) 0.0516(9) Uani 1 1 d . . . . .
H7 H 0.9399 1.0962 1.1462 0.062 Uiso 1 1 calc R U . . .
C8 C 0.9024(4) 0.9547(4) 1.06364(17) 0.0475(8) Uani 1 1 d . . . . .
H8 H 0.8579 1.0290 1.0334 0.057 Uiso 1 1 calc R U . . .
C9 C 0.9191(4) 0.8063(4) 1.04047(15) 0.0424(7) Uani 1 1 d . . . . .
C11 C 0.8428(4) 0.6163(3) 0.95801(16) 0.0468(8) Uani 1 1 d . . . . .
H11A H 0.8170 0.6030 0.9073 0.056 Uiso 1 1 calc R U . . .
H11B H 0.7546 0.5800 0.9865 0.056 Uiso 1 1 calc R U . . .
C12 C 0.9844(4) 0.5232(4) 0.97583(16) 0.0425(8) Uani 1 1 d . . . . .
H12 H 1.0743 0.5543 0.9462 0.051 Uiso 1 1 calc R U . . .
C13 C 0.9556(4) 0.3518(4) 0.97087(17) 0.0480(8) Uani 1 1 d . . . . .
H13 H 1.0566 0.2981 0.9673 0.058 Uiso 1 1 calc R U . . .
C14 C 0.8524(4) 0.2999(4) 0.91054(17) 0.0502(8) Uani 1 1 d . . . . .
C15 C 0.9110(4) 0.3165(4) 0.83735(16) 0.0527(9) Uani 1 1 d . . . . .
C16 C 0.8105(5) 0.3016(5) 0.78115(19) 0.0663(11) Uani 1 1 d . . . . .
H16 H 0.7055 0.2786 0.7899 0.080 Uiso 1 1 calc R U . . .
C17 C 0.8613(5) 0.3198(6) 0.7125(2) 0.0788(13) Uani 1 1 d . . . . .
H17 H 0.7913 0.3086 0.6742 0.095 Uiso 1 1 calc R U . . .
C18 C 1.0113(6) 0.3538(7) 0.6993(2) 0.0953(18) Uani 1 1 d . . . . .
H18 H 1.0461 0.3643 0.6518 0.114 Uiso 1 1 calc R U . . .
C19 C 1.1112(7) 0.3726(9) 0.7539(2) 0.136(3) Uani 1 1 d . . . . .
H19 H 1.2150 0.3997 0.7446 0.163 Uiso 1 1 calc R U . . .
C20 C 1.0620(5) 0.3524(8) 0.8229(2) 0.101(2) Uani 1 1 d . . . . .
H20 H 1.1330 0.3634 0.8608 0.122 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.360(4) . ?
O1 C13 1.442(4) . ?
O2 C2 1.198(4) . ?
O10 C9 1.382(4) . ?
O10 C11 1.440(4) . ?
O14 C14 1.221(4) . ?
C2 C3 1.513(5) . ?
C3 C4 1.503(4) . ?
C3 C12 1.529(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.385(4) . ?
C4 C9 1.387(4) . ?
C5 C6 1.384(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(5) . ?
C8 H8 0.9500 . ?
C11 C12 1.517(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.532(4) . ?
C12 H12 1.0000 . ?
C13 C14 1.520(5) . ?
C13 H13 1.0000 . ?
C14 C15 1.479(5) . ?
C15 C20 1.379(6) . ?
C15 C16 1.380(5) . ?
C16 C17 1.378(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.362(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.358(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(6) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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 C13 109.8(3) . . ?
C9 O10 C11 114.9(2) . . ?
O2 C2 O1 121.1(3) . . ?
O2 C2 C3 129.2(3) . . ?
O1 C2 C3 109.7(3) . . ?
C4 C3 C2 115.0(3) . . ?
C4 C3 C12 113.9(3) . . ?
C2 C3 C12 102.8(3) . . ?
C4 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
C12 C3 H3 108.3 . . ?
C5 C4 C9 118.1(3) . . ?
C5 C4 C3 121.5(3) . . ?
C9 C4 C3 120.3(3) . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C6 C5 118.9(3) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
O10 C9 C8 116.7(3) . . ?
O10 C9 C4 122.4(3) . . ?
C8 C9 C4 120.9(3) . . ?
O10 C11 C12 110.5(3) . . ?
O10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
O10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C3 108.7(3) . . ?
C11 C12 C13 112.7(3) . . ?
C3 C12 C13 101.1(3) . . ?
C11 C12 H12 111.3 . . ?
C3 C12 H12 111.3 . . ?
C13 C12 H12 111.3 . . ?
O1 C13 C14 108.9(3) . . ?
O1 C13 C12 104.6(2) . . ?
C14 C13 C12 116.0(3) . . ?
O1 C13 H13 109.0 . . ?
C14 C13 H13 109.0 . . ?
C12 C13 H13 109.0 . . ?
O14 C14 C15 121.9(3) . . ?
O14 C14 C13 120.3(3) . . ?
C15 C14 C13 117.8(3) . . ?
C20 C15 C16 118.3(3) . . ?
C20 C15 C14 122.4(3) . . ?
C16 C15 C14 119.3(3) . . ?
C17 C16 C15 120.5(4) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.0(5) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.7(4) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?

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
C13 O1 C2 O2 -174.7(3) . . . . ?
C13 O1 C2 C3 5.4(4) . . . . ?
O2 C2 C3 C4 -38.8(5) . . . . ?
O1 C2 C3 C4 141.1(3) . . . . ?
O2 C2 C3 C12 -163.2(4) . . . . ?
O1 C2 C3 C12 16.7(3) . . . . ?
C2 C3 C4 C5 70.9(4) . . . . ?
C12 C3 C4 C5 -170.8(3) . . . . ?
C2 C3 C4 C9 -113.1(3) . . . . ?
C12 C3 C4 C9 5.2(4) . . . . ?
C9 C4 C5 C6 -1.9(5) . . . . ?
C3 C4 C5 C6 174.2(3) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C5 C6 C7 C8 1.2(6) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C11 O10 C9 C8 -161.2(3) . . . . ?
C11 O10 C9 C4 20.6(4) . . . . ?
C7 C8 C9 O10 -179.5(3) . . . . ?
C7 C8 C9 C4 -1.3(5) . . . . ?
C5 C4 C9 O10 -179.4(3) . . . . ?
C3 C4 C9 O10 4.5(5) . . . . ?
C5 C4 C9 C8 2.5(5) . . . . ?
C3 C4 C9 C8 -173.6(3) . . . . ?
C9 O10 C11 C12 -54.0(4) . . . . ?
O10 C11 C12 C3 61.1(3) . . . . ?
O10 C11 C12 C13 172.4(2) . . . . ?
C4 C3 C12 C11 -36.4(4) . . . . ?
C2 C3 C12 C11 88.6(3) . . . . ?
C4 C3 C12 C13 -155.2(3) . . . . ?
C2 C3 C12 C13 -30.1(3) . . . . ?
C2 O1 C13 C14 -150.1(3) . . . . ?
C2 O1 C13 C12 -25.5(3) . . . . ?
C11 C12 C13 O1 -81.8(3) . . . . ?
C3 C12 C13 O1 34.1(3) . . . . ?
C11 C12 C13 C14 38.2(4) . . . . ?
C3 C12 C13 C14 154.0(3) . . . . ?
O1 C13 C14 O14 6.8(4) . . . . ?
C12 C13 C14 O14 -110.8(4) . . . . ?
O1 C13 C14 C15 -174.6(3) . . . . ?
C12 C13 C14 C15 67.8(4) . . . . ?
O14 C14 C15 C20 -170.4(4) . . . . ?
C13 C14 C15 C20 11.1(6) . . . . ?
O14 C14 C15 C16 12.2(5) . . . . ?
C13 C14 C15 C16 -166.3(3) . . . . ?
C20 C15 C16 C17 1.1(7) . . . . ?
C14 C15 C16 C17 178.6(4) . . . . ?
C15 C16 C17 C18 -0.4(8) . . . . ?
C16 C17 C18 C19 -1.2(10) . . . . ?
C17 C18 C19 C20 2.1(11) . . . . ?
C16 C15 C20 C19 -0.1(8) . . . . ?
C14 C15 C20 C19 -177.5(5) . . . . ?
C18 C19 C20 C15 -1.5(10) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/hexane'
