# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_dibenzobarrelene_293K
_database_code_depnum_ccdc_archive 'CCDC 1860420'
_audit_update_record             
;
2018-08-06 deposited with the CCDC.
2018-10-02 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C32 H24 O2'
_chemical_formula_moiety         'C32 H24 O2'
_chemical_formula_weight         440.54
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.2639(3)
_cell_length_b                   10.1820(4)
_cell_length_c                   14.3848(5)
_cell_angle_alpha                102.8842(19)
_cell_angle_beta                 99.249(2)
_cell_angle_gamma                112.0041(19)
_cell_volume                     1180.70(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12835
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464.00
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_T_max  0.942

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

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            19409
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         3.274
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4231
_reflns_number_gt                2685
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0912
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1410
_refine_ls_wR_factor_gt          0.1206
_refine_ls_number_restraints     72
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         4231
_refine_ls_number_parameters     418
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0798P)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         0.16
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 0.49757(18) 0.34736(16) 0.56739(10) 0.0818(4) Uani 1 1 d . . . . .
C1 C 0.75424(19) 0.48783(16) 0.78570(11) 0.0448(4) Uani 1 1 d . . . . .
O2 O 0.75460(19) 0.29526(14) 0.84871(10) 0.0784(4) Uani 1 1 d . . . . .
C4 C 0.82827(19) 0.75395(16) 0.83530(12) 0.0469(4) Uani 1 1 d . . . . .
C5 C 1.0379(2) 0.66632(17) 0.83587(13) 0.0489(4) Uani 1 1 d . . . . .
C6 C 0.8777(2) 0.63718(16) 0.86324(11) 0.0469(4) Uani 1 1 d . . . . .
C7 C 0.74277(19) 0.48518(16) 0.69199(12) 0.0463(4) Uani 1 1 d . . . . .
C8 C 1.0261(2) 0.66178(17) 0.73681(13) 0.0506(5) Uani 1 1 d . . . . .
C9 C 0.6315(2) 0.35724(18) 0.60224(12) 0.0517(5) Uani 1 1 d . . . . .
C10 C 0.8169(2) 0.75015(17) 0.73676(12) 0.0491(4) Uani 1 1 d . . . . .
C11 C 0.6729(2) 0.35539(18) 0.81809(12) 0.0524(5) Uani 1 1 d . . . . .
C12 C 0.6884(2) 0.24764(17) 0.55583(12) 0.0514(5) Uani 1 1 d . . . . .
C13 C 0.8574(2) 0.63032(17) 0.67718(11) 0.0491(5) Uani 1 1 d . . . . .
C14 C 0.7985(2) 0.85925(19) 0.89830(16) 0.0587(5) Uani 1 1 d . . . . .
C16 C 0.7744(2) 0.8502(2) 0.70171(17) 0.0611(5) Uani 1 1 d . . . . .
C17 C 0.8852(3) 0.6383(2) 0.96972(13) 0.0613(5) Uani 1 1 d . . . . .
C18 C 1.1842(2) 0.6984(2) 0.89878(17) 0.0617(5) Uani 1 1 d . . . . .
C19 C 0.6011(3) 0.1487(2) 0.46220(14) 0.0686(6) Uani 1 1 d . . . . .
H19 H 0.5092 0.1532 0.4288 0.082 Uiso 1 1 calc R U . . .
C20 C 0.7566(2) 0.9598(2) 0.86202(19) 0.0671(6) Uani 1 1 d . . . . .
C21 C 1.1618(3) 0.6873(2) 0.70207(18) 0.0669(6) Uani 1 1 d . . . . .
C22 C 0.7443(2) 0.9553(2) 0.76543(19) 0.0681(6) Uani 1 1 d . . . . .
C23 C 0.8248(3) 0.2402(2) 0.60385(14) 0.0663(5) Uani 1 1 d . . . . .
H23 H 0.8860 0.3077 0.6661 0.080 Uiso 1 1 calc R U . . .
C24 C 0.8428(3) 0.6232(3) 0.56889(15) 0.0670(6) Uani 1 1 d . . . . .
C25 C 1.3080(3) 0.7191(3) 0.7661(2) 0.0819(7) Uani 1 1 d . . . . .
C27 C 1.3195(3) 0.7248(2) 0.8627(2) 0.0791(7) Uani 1 1 d . . . . .
C29 C 0.6494(4) 0.0445(2) 0.41855(17) 0.0868(7) Uani 1 1 d . . . . .
H29 H 0.5911 -0.0204 0.3552 0.104 Uiso 1 1 calc R U . . .
C30 C 0.7818(4) 0.0353(2) 0.4672(2) 0.0919(8) Uani 1 1 d . . . . .
H30 H 0.8123 -0.0374 0.4375 0.110 Uiso 1 1 calc R U . . .
C31 C 0.8712(3) 0.1327(3) 0.55980(18) 0.0869(7) Uani 1 1 d . . . . .
H31 H 0.9622 0.1264 0.5927 0.104 Uiso 1 1 calc R U . . .
H14 H 0.804(2) 0.8596(18) 0.9649(14) 0.059(5) Uiso 1 1 d . . . . .
H16 H 0.765(2) 0.8457(19) 0.6331(14) 0.065(5) Uiso 1 1 d . . . . .
H17A H 0.967(2) 0.739(2) 1.0163(13) 0.066(5) Uiso 1 1 d . . . . .
H17B H 0.773(3) 0.616(2) 0.9818(13) 0.070(6) Uiso 1 1 d . . . . .
H17C H 0.924(2) 0.560(2) 0.9849(13) 0.081(6) Uiso 1 1 d . . . . .
H18 H 1.194(2) 0.7024(18) 0.9645(14) 0.056(5) Uiso 1 1 d . . . . .
H20 H 0.738(2) 1.031(2) 0.9095(15) 0.077(6) Uiso 1 1 d . . . . .
H21 H 1.151(2) 0.6831(19) 0.6346(14) 0.066(6) Uiso 1 1 d . . . . .
H22 H 0.714(2) 1.024(2) 0.7411(14) 0.087(7) Uiso 1 1 d . . . . .
H24A H 0.869(2) 0.541(2) 0.5326(15) 0.078(6) Uiso 1 1 d . . . . .
H24B H 0.729(3) 0.599(2) 0.5315(15) 0.085(7) Uiso 1 1 d . . . . .
H24C H 0.918(2) 0.720(2) 0.5660(13) 0.072(6) Uiso 1 1 d . . . . .
H25 H 1.401(3) 0.737(3) 0.7424(17) 0.110(8) Uiso 1 1 d . . . . .
H27 H 1.419(3) 0.745(2) 0.9089(15) 0.078(6) Uiso 1 1 d . . . . .
C27A C 0.510(3) 0.290(3) 0.816(2) 0.053(4) Uani 0.44(3) 1 d . U P A 1
C28A C 0.444(2) 0.1600(16) 0.8393(13) 0.053(2) Uani 0.44(3) 1 d . U P A 1
H28A H 0.5094 0.1142 0.8574 0.063 Uiso 0.44(3) 1 calc R U P A 1
C29A C 0.2844(18) 0.0982(14) 0.8359(10) 0.064(3) Uani 0.44(3) 1 d . U P A 1
H29A H 0.2402 0.0075 0.8483 0.077 Uiso 0.44(3) 1 calc R U P A 1
C30A C 0.1864(14) 0.1690(19) 0.8142(9) 0.066(3) Uani 0.44(3) 1 d . U P A 1
H30A H 0.0781 0.1258 0.8137 0.079 Uiso 0.44(3) 1 calc R U P A 1
C31A C 0.2470(19) 0.302(2) 0.7935(12) 0.076(3) Uani 0.44(3) 1 d . U P A 1
H31A H 0.1841 0.3516 0.7807 0.091 Uiso 0.44(3) 1 calc R U P A 1
C32A C 0.413(2) 0.3571(19) 0.7930(15) 0.064(3) Uani 0.44(3) 1 d . U P A 1
H32A H 0.4571 0.4439 0.7761 0.077 Uiso 0.44(3) 1 calc R U P A 1
C27B C 0.494(2) 0.309(2) 0.8128(15) 0.050(3) Uani 0.56(3) 1 d . U P A 2
C28B C 0.4014(17) 0.1784(14) 0.8316(10) 0.064(3) Uani 0.56(3) 1 d . U P A 2
H28B H 0.4521 0.1208 0.8495 0.077 Uiso 0.56(3) 1 calc R U P A 2
C29B C 0.2402(15) 0.1318(12) 0.8249(6) 0.069(3) Uani 0.56(3) 1 d . U P A 2
H29B H 0.1820 0.0438 0.8372 0.082 Uiso 0.56(3) 1 calc R U P A 2
C30B C 0.1667(16) 0.2177(15) 0.7997(7) 0.075(2) Uani 0.56(3) 1 d . U P A 2
H30B H 0.0572 0.1880 0.7953 0.090 Uiso 0.56(3) 1 calc R U P A 2
C31B C 0.2526(13) 0.3478(15) 0.7806(10) 0.077(2) Uani 0.56(3) 1 d . U P A 2
H31B H 0.2001 0.4041 0.7629 0.092 Uiso 0.56(3) 1 calc R U P A 2
C32B C 0.4132(18) 0.3947(14) 0.7874(12) 0.058(2) Uani 0.56(3) 1 d . U P A 2
H32B H 0.4699 0.4833 0.7752 0.070 Uiso 0.56(3) 1 calc R U P A 2


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# 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 C9 1.219(2) . ?
C1 C7 1.328(2) . ?
C1 C11 1.495(2) . ?
C1 C6 1.548(2) . ?
O2 C11 1.226(2) . ?
C4 C14 1.384(2) . ?
C4 C10 1.395(2) . ?
C4 C6 1.532(2) . ?
C5 C18 1.380(3) . ?
C5 C8 1.400(2) . ?
C5 C6 1.535(2) . ?
C6 C17 1.519(2) . ?
C7 C9 1.497(2) . ?
C7 C13 1.547(2) . ?
C8 C21 1.383(3) . ?
C8 C13 1.534(2) . ?
C9 C12 1.480(3) . ?
C10 C16 1.382(2) . ?
C10 C13 1.531(2) . ?
C11 C27A 1.39(3) . ?
C11 C27B 1.53(2) . ?
C12 C23 1.376(2) . ?
C12 C19 1.385(2) . ?
C13 C24 1.525(2) . ?
C14 C20 1.394(3) . ?
C14 H14 0.951(18) . ?
C16 C22 1.390(3) . ?
C16 H16 0.966(18) . ?
C17 H17A 1.010(19) . ?
C17 H17B 1.03(2) . ?
C17 H17C 1.03(2) . ?
C18 C27 1.390(3) . ?
C18 H18 0.926(17) . ?
C19 C29 1.367(3) . ?
C19 H19 0.9300 . ?
C20 C22 1.365(3) . ?
C20 H20 0.96(2) . ?
C21 C25 1.387(3) . ?
C21 H21 0.949(18) . ?
C22 H22 0.96(2) . ?
C23 C31 1.384(3) . ?
C23 H23 0.9300 . ?
C24 H24A 1.02(2) . ?
C24 H24B 1.01(2) . ?
C24 H24C 0.99(2) . ?
C25 C27 1.361(3) . ?
C25 H25 0.94(3) . ?
C27 H27 0.97(2) . ?
C29 C30 1.357(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.373(3) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C27A C32A 1.36(2) . ?
C27A C28A 1.38(2) . ?
C28A C29A 1.363(15) . ?
C28A H28A 0.9300 . ?
C29A C30A 1.394(12) . ?
C29A H29A 0.9300 . ?
C30A C31A 1.375(13) . ?
C30A H30A 0.9300 . ?
C31A C32A 1.43(2) . ?
C31A H31A 0.9300 . ?
C32A H32A 0.9300 . ?
C27B C28B 1.402(18) . ?
C27B C32B 1.408(15) . ?
C28B C29B 1.366(12) . ?
C28B H28B 0.9300 . ?
C29B C30B 1.367(10) . ?
C29B H29B 0.9300 . ?
C30B C31B 1.381(9) . ?
C30B H30B 0.9300 . ?
C31B C32B 1.361(15) . ?
C31B H31B 0.9300 . ?
C32B H32B 0.9300 . ?

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
C7 C1 C11 124.71(13) . . ?
C7 C1 C6 114.83(13) . . ?
C11 C1 C6 120.06(13) . . ?
C14 C4 C10 119.80(16) . . ?
C14 C4 C6 126.08(16) . . ?
C10 C4 C6 114.12(14) . . ?
C18 C5 C8 120.35(17) . . ?
C18 C5 C6 126.46(16) . . ?
C8 C5 C6 113.17(14) . . ?
C17 C6 C4 114.10(15) . . ?
C17 C6 C5 114.64(15) . . ?
C4 C6 C5 104.31(12) . . ?
C17 C6 C1 113.67(14) . . ?
C4 C6 C1 104.25(13) . . ?
C5 C6 C1 104.71(12) . . ?
C1 C7 C9 126.31(14) . . ?
C1 C7 C13 115.14(13) . . ?
C9 C7 C13 118.54(13) . . ?
C21 C8 C5 119.42(18) . . ?
C21 C8 C13 126.25(17) . . ?
C5 C8 C13 114.32(14) . . ?
O1 C9 C12 121.27(16) . . ?
O1 C9 C7 119.47(16) . . ?
C12 C9 C7 119.24(17) . . ?
C16 C10 C4 120.21(17) . . ?
C16 C10 C13 126.11(16) . . ?
C4 C10 C13 113.68(14) . . ?
O2 C11 C27A 115.5(10) . . ?
O2 C11 C1 118.10(18) . . ?
C27A C11 C1 126.4(10) . . ?
O2 C11 C27B 125.5(7) . . ?
C1 C11 C27B 116.4(7) . . ?
C23 C12 C19 119.08(18) . . ?
C23 C12 C9 121.70(15) . . ?
C19 C12 C9 119.22(19) . . ?
C24 C13 C10 114.25(15) . . ?
C24 C13 C8 114.70(16) . . ?
C10 C13 C8 104.50(13) . . ?
C24 C13 C7 113.90(14) . . ?
C10 C13 C7 103.69(13) . . ?
C8 C13 C7 104.58(13) . . ?
C4 C14 C20 119.3(2) . . ?
C4 C14 H14 119.2(10) . . ?
C20 C14 H14 121.4(10) . . ?
C10 C16 C22 119.6(2) . . ?
C10 C16 H16 119.8(11) . . ?
C22 C16 H16 120.6(11) . . ?
C6 C17 H17A 109.6(10) . . ?
C6 C17 H17B 109.9(10) . . ?
H17A C17 H17B 109.6(14) . . ?
C6 C17 H17C 110.4(10) . . ?
H17A C17 H17C 107.0(15) . . ?
H17B C17 H17C 110.3(15) . . ?
C5 C18 C27 119.4(2) . . ?
C5 C18 H18 121.1(11) . . ?
C27 C18 H18 119.5(11) . . ?
C29 C19 C12 120.3(2) . . ?
C29 C19 H19 119.8 . . ?
C12 C19 H19 119.8 . . ?
C22 C20 C14 120.8(2) . . ?
C22 C20 H20 123.8(11) . . ?
C14 C20 H20 115.4(12) . . ?
C8 C21 C25 119.5(2) . . ?
C8 C21 H21 118.2(11) . . ?
C25 C21 H21 122.2(11) . . ?
C20 C22 C16 120.2(2) . . ?
C20 C22 H22 120.0(12) . . ?
C16 C22 H22 119.7(12) . . ?
C12 C23 C31 120.17(19) . . ?
C12 C23 H23 119.9 . . ?
C31 C23 H23 119.9 . . ?
C13 C24 H24A 110.9(11) . . ?
C13 C24 H24B 112.4(12) . . ?
H24A C24 H24B 105.4(16) . . ?
C13 C24 H24C 108.8(11) . . ?
H24A C24 H24C 110.1(16) . . ?
H24B C24 H24C 109.2(16) . . ?
C27 C25 C21 120.9(2) . . ?
C27 C25 H25 119.6(15) . . ?
C21 C25 H25 119.5(15) . . ?
C25 C27 C18 120.4(2) . . ?
C25 C27 H27 122.9(12) . . ?
C18 C27 H27 116.7(12) . . ?
C30 C29 C19 120.4(2) . . ?
C30 C29 H29 119.8 . . ?
C19 C29 H29 119.8 . . ?
C29 C30 C31 120.5(2) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C30 C31 C23 119.5(2) . . ?
C30 C31 H31 120.2 . . ?
C23 C31 H31 120.2 . . ?
C32A C27A C28A 118.3(19) . . ?
C32A C27A C11 120.1(19) . . ?
C28A C27A C11 121.6(18) . . ?
C29A C28A C27A 120.4(13) . . ?
C29A C28A H28A 119.8 . . ?
C27A C28A H28A 119.8 . . ?
C28A C29A C30A 120.9(11) . . ?
C28A C29A H29A 119.6 . . ?
C30A C29A H29A 119.6 . . ?
C31A C30A C29A 121.1(11) . . ?
C31A C30A H30A 119.4 . . ?
C29A C30A H30A 119.4 . . ?
C30A C31A C32A 115.6(10) . . ?
C30A C31A H31A 122.2 . . ?
C32A C31A H31A 122.2 . . ?
C27A C32A C31A 123.6(14) . . ?
C27A C32A H32A 118.2 . . ?
C31A C32A H32A 118.2 . . ?
C28B C27B C32B 116.9(13) . . ?
C28B C27B C11 121.2(12) . . ?
C32B C27B C11 121.9(13) . . ?
C29B C28B C27B 122.8(9) . . ?
C29B C28B H28B 118.6 . . ?
C27B C28B H28B 118.6 . . ?
C28B C29B C30B 118.4(8) . . ?
C28B C29B H29B 120.8 . . ?
C30B C29B H29B 120.8 . . ?
C29B C30B C31B 120.9(9) . . ?
C29B C30B H30B 119.5 . . ?
C31B C30B H30B 119.5 . . ?
C32B C31B C30B 120.8(9) . . ?
C32B C31B H31B 119.6 . . ?
C30B C31B H31B 119.6 . . ?
C31B C32B C27B 120.2(10) . . ?
C31B C32B H32B 119.9 . . ?
C27B C32B H32B 119.9 . . ?

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 C4 C6 C17 2.9(2) . . . . ?
C10 C4 C6 C17 -178.25(15) . . . . ?
C14 C4 C6 C5 -122.91(17) . . . . ?
C10 C4 C6 C5 55.90(17) . . . . ?
C14 C4 C6 C1 127.51(16) . . . . ?
C10 C4 C6 C1 -53.68(17) . . . . ?
C18 C5 C6 C17 -2.8(2) . . . . ?
C8 C5 C6 C17 178.87(15) . . . . ?
C18 C5 C6 C4 122.67(17) . . . . ?
C8 C5 C6 C4 -55.62(16) . . . . ?
C18 C5 C6 C1 -128.08(17) . . . . ?
C8 C5 C6 C1 53.62(16) . . . . ?
C7 C1 C6 C17 178.53(16) . . . . ?
C11 C1 C6 C17 -8.4(2) . . . . ?
C7 C1 C6 C4 53.68(17) . . . . ?
C11 C1 C6 C4 -133.29(16) . . . . ?
C7 C1 C6 C5 -55.62(18) . . . . ?
C11 C1 C6 C5 117.42(16) . . . . ?
C11 C1 C7 C9 8.6(3) . . . . ?
C6 C1 C7 C9 -178.70(16) . . . . ?
C11 C1 C7 C13 -171.34(16) . . . . ?
C6 C1 C7 C13 1.3(2) . . . . ?
C18 C5 C8 C21 1.1(2) . . . . ?
C6 C5 C8 C21 179.47(14) . . . . ?
C18 C5 C8 C13 -177.89(14) . . . . ?
C6 C5 C8 C13 0.52(19) . . . . ?
C1 C7 C9 O1 90.6(2) . . . . ?
C13 C7 C9 O1 -89.4(2) . . . . ?
C1 C7 C9 C12 -91.2(2) . . . . ?
C13 C7 C9 C12 88.75(19) . . . . ?
C14 C4 C10 C16 -0.6(2) . . . . ?
C6 C4 C10 C16 -179.54(15) . . . . ?
C14 C4 C10 C13 178.53(15) . . . . ?
C6 C4 C10 C13 -0.37(19) . . . . ?
C7 C1 C11 O2 102.1(2) . . . . ?
C6 C1 C11 O2 -70.2(2) . . . . ?
C7 C1 C11 C27A -76.9(14) . . . . ?
C6 C1 C11 C27A 110.8(14) . . . . ?
C7 C1 C11 C27B -79.7(9) . . . . ?
C6 C1 C11 C27B 108.0(9) . . . . ?
O1 C9 C12 C23 -167.37(17) . . . . ?
C7 C9 C12 C23 14.5(2) . . . . ?
O1 C9 C12 C19 11.8(3) . . . . ?
C7 C9 C12 C19 -166.35(15) . . . . ?
C16 C10 C13 C24 -1.8(2) . . . . ?
C4 C10 C13 C24 179.05(16) . . . . ?
C16 C10 C13 C8 124.32(17) . . . . ?
C4 C10 C13 C8 -54.80(16) . . . . ?
C16 C10 C13 C7 -126.38(18) . . . . ?
C4 C10 C13 C7 54.50(17) . . . . ?
C21 C8 C13 C24 1.9(2) . . . . ?
C5 C8 C13 C24 -179.26(15) . . . . ?
C21 C8 C13 C10 -123.99(18) . . . . ?
C5 C8 C13 C10 54.87(16) . . . . ?
C21 C8 C13 C7 127.36(17) . . . . ?
C5 C8 C13 C7 -53.78(16) . . . . ?
C1 C7 C13 C24 179.32(17) . . . . ?
C9 C7 C13 C24 -0.7(2) . . . . ?
C1 C7 C13 C10 -55.91(18) . . . . ?
C9 C7 C13 C10 124.12(15) . . . . ?
C1 C7 C13 C8 53.34(18) . . . . ?
C9 C7 C13 C8 -126.64(16) . . . . ?
C10 C4 C14 C20 0.3(2) . . . . ?
C6 C4 C14 C20 179.07(16) . . . . ?
C4 C10 C16 C22 0.5(3) . . . . ?
C13 C10 C16 C22 -178.57(16) . . . . ?
C8 C5 C18 C27 -0.6(3) . . . . ?
C6 C5 C18 C27 -178.79(17) . . . . ?
C23 C12 C19 C29 0.5(3) . . . . ?
C9 C12 C19 C29 -178.71(17) . . . . ?
C4 C14 C20 C22 0.2(3) . . . . ?
C5 C8 C21 C25 -0.9(3) . . . . ?
C13 C8 C21 C25 177.93(17) . . . . ?
C14 C20 C22 C16 -0.3(3) . . . . ?
C10 C16 C22 C20 0.0(3) . . . . ?
C19 C12 C23 C31 -1.6(3) . . . . ?
C9 C12 C23 C31 177.56(17) . . . . ?
C8 C21 C25 C27 0.3(3) . . . . ?
C21 C25 C27 C18 0.2(3) . . . . ?
C5 C18 C27 C25 0.0(3) . . . . ?
C12 C19 C29 C30 1.1(3) . . . . ?
C19 C29 C30 C31 -1.5(3) . . . . ?
C29 C30 C31 C23 0.4(3) . . . . ?
C12 C23 C31 C30 1.2(3) . . . . ?
O2 C11 C27A C32A 173.2(15) . . . . ?
C1 C11 C27A C32A -8(3) . . . . ?
O2 C11 C27A C28A -5(3) . . . . ?
C1 C11 C27A C28A 174.1(14) . . . . ?
C32A C27A C28A C29A 2(3) . . . . ?
C11 C27A C28A C29A -179.6(17) . . . . ?
C27A C28A C29A C30A -4(2) . . . . ?
C28A C29A C30A C31A 1(2) . . . . ?
C29A C30A C31A C32A 2(2) . . . . ?
C28A C27A C32A C31A 1(3) . . . . ?
C11 C27A C32A C31A -177.0(19) . . . . ?
C30A C31A C32A C27A -3(3) . . . . ?
O2 C11 C27B C28B -8(2) . . . . ?
C1 C11 C27B C28B 173.5(12) . . . . ?
O2 C11 C27B C32B 172.5(10) . . . . ?
C1 C11 C27B C32B -5.6(18) . . . . ?
C32B C27B C28B C29B 1(2) . . . . ?
C11 C27B C28B C29B -178.1(12) . . . . ?
C27B C28B C29B C30B -0.7(18) . . . . ?
C28B C29B C30B C31B 0.5(13) . . . . ?
C29B C30B C31B C32B -0.6(16) . . . . ?
C30B C31B C32B C27B 1(2) . . . . ?
C28B C27B C32B C31B -1(2) . . . . ?
C11 C27B C32B C31B 178.1(15) . . . . ?

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

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

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_dibenzobarrelene_223K_UV
_database_code_depnum_ccdc_archive 'CCDC 1860422'
_audit_update_record             
;
2018-08-06 deposited with the CCDC.
2018-10-02 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C32 H24 O2'
_chemical_formula_moiety         'C32 H24 O2'
_chemical_formula_weight         440.54
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.2358(7)
_cell_length_b                   10.1367(9)
_cell_length_c                   14.2857(13)
_cell_angle_alpha                102.730(3)
_cell_angle_beta                 99.234(3)
_cell_angle_gamma                111.955(2)
_cell_volume                     1165.53(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7548
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464.00
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.985

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

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            11483
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.035
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5284
_reflns_number_gt                3356
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0701
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.0893
_refine_ls_number_restraints     72
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         5284
_refine_ls_number_parameters     438
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0507P)²+0.1053P] 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         0.24
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 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 0.0106 0.0060
;
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 0.24625(15) 0.70520(13) 0.14959(9) 0.0577(3) Uani 1 1 d . . . . .
O2 O 0.50352(13) 0.65150(13) 0.43322(8) 0.0589(3) Uani 1 1 d . . . . .
C3 C 0.18274(15) 0.24838(14) 0.26361(10) 0.0346(3) Uani 1 1 d . . . . .
C4 C -0.03860(15) 0.33297(14) 0.16396(10) 0.0343(3) Uani 1 1 d . . . . .
C5 C 0.31242(16) 0.75283(15) 0.44457(10) 0.0369(3) Uani 1 1 d . . . . .
C6 C 0.17115(14) 0.24455(14) 0.16409(10) 0.0335(3) Uani 1 1 d . . . . .
C7 C 0.24559(15) 0.51210(14) 0.21396(9) 0.0318(3) Uani 1 1 d . . . . .
C8 C 0.12173(15) 0.36226(14) 0.13619(9) 0.0329(3) Uani 1 1 d . . . . .
C9 C 0.32699(17) 0.64453(15) 0.18096(10) 0.0377(3) Uani 1 1 d . . . . .
C10 C 0.37003(16) 0.64302(15) 0.39836(10) 0.0365(3) Uani 1 1 d . . . . .
C11 C -0.02692(16) 0.33787(15) 0.26363(10) 0.0363(3) Uani 1 1 d . . . . .
C12 C 0.14249(15) 0.36890(15) 0.32328(10) 0.0347(3) Uani 1 1 d . . . . .
C13 C 0.25741(15) 0.51453(14) 0.30826(9) 0.0325(3) Uani 1 1 d . . . . .
C14 C 0.20182(16) 0.13958(16) 0.10091(12) 0.0418(3) Uani 1 1 d . . . . .
C15 C 0.22572(17) 0.14820(16) 0.29920(12) 0.0429(4) Uani 1 1 d . . . . .
C16 C -0.18527(18) 0.30124(17) 0.10020(12) 0.0444(4) Uani 1 1 d . . . . .
C18 C 0.1138(2) 0.36100(18) 0.02907(10) 0.0423(3) Uani 1 1 d . . . . .
C19 C 0.24396(17) 0.03834(17) 0.13748(13) 0.0474(4) Uani 1 1 d . . . . .
C20 C 0.25591(18) 0.04279(17) 0.23521(13) 0.0484(4) Uani 1 1 d . . . . .
C21 C 0.1759(2) 0.76194(18) 0.39587(12) 0.0475(4) Uani 1 1 d . . . . .
C22 C -0.16236(18) 0.31225(18) 0.29934(13) 0.0479(4) Uani 1 1 d . . . . .
C23 C 0.4010(2) 0.85225(18) 0.53946(11) 0.0495(4) Uani 1 1 d . . . . .
C24 C 0.1570(2) 0.3758(2) 0.43215(11) 0.0471(4) Uani 1 1 d . . . . .
C25 C -0.30958(19) 0.2805(2) 0.23470(15) 0.0593(5) Uani 1 1 d . . . . .
C26 C -0.32112(19) 0.2746(2) 0.13683(15) 0.0574(5) Uani 1 1 d . . . . .
C28 C 0.1308(3) 0.8710(2) 0.44061(15) 0.0630(5) Uani 1 1 d . . . . .
C29 C 0.2203(3) 0.9684(2) 0.53397(15) 0.0672(5) Uani 1 1 d . . . . .
C31 C 0.3535(3) 0.95794(19) 0.58325(14) 0.0631(5) Uani 1 1 d . . . . .
H14 H 0.1922(17) 0.1362(17) 0.0309(11) 0.041(4) Uiso 1 1 d . . . . .
H15 H 0.2341(19) 0.1537(18) 0.3728(12) 0.053(4) Uiso 1 1 d . . . . .
H16 H -0.1937(19) 0.2969(18) 0.0308(13) 0.050(4) Uiso 1 1 d . . . . .
H18A H 0.0776(18) 0.4382(19) 0.0126(11) 0.048(4) Uiso 1 1 d . . . . .
H18B H 0.2246(19) 0.3852(18) 0.0168(11) 0.049(4) Uiso 1 1 d . . . . .
H18C H 0.0360(18) 0.2604(19) -0.0187(11) 0.048(4) Uiso 1 1 d . . . . .
H19 H 0.2646(19) -0.033(2) 0.0927(12) 0.057(5) Uiso 1 1 d . . . . .
H20 H 0.2867(19) -0.030(2) 0.2595(12) 0.057(5) Uiso 1 1 d . . . . .
H21 H 0.113(2) 0.6924(19) 0.3283(13) 0.056(5) Uiso 1 1 d . . . . .
H22 H -0.1543(19) 0.3155(18) 0.3711(12) 0.055(5) Uiso 1 1 d . . . . .
H23 H 0.498(2) 0.8427(19) 0.5730(13) 0.060(5) Uiso 1 1 d . . . . .
H24A H 0.080(2) 0.276(2) 0.4347(12) 0.052(4) Uiso 1 1 d . . . . .
H24B H 0.270(2) 0.3949(19) 0.4692(13) 0.060(5) Uiso 1 1 d . . . . .
H24C H 0.1265(19) 0.456(2) 0.4674(12) 0.054(5) Uiso 1 1 d . . . . .
H25 H -0.404(2) 0.263(2) 0.2594(14) 0.075(6) Uiso 1 1 d . . . . .
H26 H -0.426(2) 0.2542(19) 0.0896(13) 0.064(5) Uiso 1 1 d . . . . .
H28 H 0.035(3) 0.877(2) 0.4062(15) 0.086(7) Uiso 1 1 d . . . . .
H29 H 0.188(3) 1.042(3) 0.5635(16) 0.091(7) Uiso 1 1 d . . . . .
H31 H 0.413(2) 1.027(2) 0.6492(15) 0.080(6) Uiso 1 1 d . . . . .
C27A C 0.5129(17) 0.6922(16) 0.1892(13) 0.034(2) Uani 0.52(2) 1 d . U P A 1
C28A C 0.5904(17) 0.6082(14) 0.2165(11) 0.0425(18) Uani 0.52(2) 1 d . U P A 1
H28A H 0.5328 0.5214 0.2323 0.051 Uiso 0.52(2) 1 calc R U P A 1
C29A C 0.7517(13) 0.6512(14) 0.2206(10) 0.0597(19) Uani 0.52(2) 1 d . U P A 1
H29A H 0.8029 0.5912 0.2363 0.072 Uiso 0.52(2) 1 calc R U P A 1
C30A C 0.8393(13) 0.7823(14) 0.2018(7) 0.057(2) Uani 0.52(2) 1 d . U P A 1
H30A H 0.9502 0.8120 0.2065 0.069 Uiso 0.52(2) 1 calc R U P A 1
C31A C 0.7654(13) 0.8695(11) 0.1765(6) 0.054(2) Uani 0.52(2) 1 d . U P A 1
H31A H 0.8251 0.9586 0.1638 0.065 Uiso 0.52(2) 1 calc R U P A 1
C32A C 0.6016(16) 0.8241(12) 0.1698(8) 0.0474(18) Uani 0.52(2) 1 d . U P A 1
H32A H 0.5498 0.8826 0.1521 0.057 Uiso 0.52(2) 1 calc R U P A 1
C32B C 0.5604(13) 0.8377(12) 0.1593(9) 0.0416(16) Uani 0.48(2) 1 d . U P A 2
H32B H 0.4962 0.8854 0.1397 0.050 Uiso 0.48(2) 1 calc R U P A 2
C31B C 0.7223(14) 0.8989(12) 0.1651(8) 0.052(2) Uani 0.48(2) 1 d . U P A 2
H31B H 0.7698 0.9910 0.1530 0.062 Uiso 0.48(2) 1 calc R U P A 2
C30B C 0.8163(11) 0.8260(14) 0.1885(7) 0.055(2) Uani 0.48(2) 1 d . U P A 2
H30B H 0.9267 0.8681 0.1902 0.067 Uiso 0.48(2) 1 calc R U P A 2
C29B C 0.7519(14) 0.6932(16) 0.2094(10) 0.060(2) Uani 0.48(2) 1 d . U P A 2
H29B H 0.8164 0.6443 0.2258 0.072 Uiso 0.48(2) 1 calc R U P A 2
C28B C 0.586(2) 0.6328(18) 0.2053(13) 0.053(3) Uani 0.48(2) 1 d . U P A 2
H28B H 0.5387 0.5415 0.2186 0.064 Uiso 0.48(2) 1 calc R U P A 2
C27B C 0.489(2) 0.704(2) 0.1823(15) 0.038(2) Uani 0.48(2) 1 d . U P A 2


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# 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 C9 1.2216(17) . ?
O2 C10 1.2166(16) . ?
C3 C15 1.3826(19) . ?
C3 C6 1.3993(19) . ?
C3 C12 1.5296(19) . ?
C4 C16 1.3846(19) . ?
C4 C11 1.3989(19) . ?
C4 C8 1.5330(18) . ?
C5 C21 1.384(2) . ?
C5 C23 1.3957(19) . ?
C5 C10 1.480(2) . ?
C6 C14 1.3824(19) . ?
C6 C8 1.5328(18) . ?
C7 C13 1.3280(18) . ?
C7 C9 1.4925(19) . ?
C7 C8 1.5489(17) . ?
C8 C18 1.5173(19) . ?
C9 C27B 1.387(16) . ?
C9 C27A 1.576(15) . ?
C10 C13 1.5012(17) . ?
C11 C22 1.383(2) . ?
C11 C12 1.5360(18) . ?
C12 C24 1.523(2) . ?
C12 C13 1.5468(19) . ?
C14 C19 1.395(2) . ?
C14 H14 0.981(15) . ?
C15 C20 1.389(2) . ?
C15 H15 1.030(17) . ?
C16 C26 1.393(2) . ?
C16 H16 0.971(17) . ?
C18 H18A 1.015(16) . ?
C18 H18B 1.013(16) . ?
C18 H18C 1.005(16) . ?
C19 C20 1.372(2) . ?
C19 H19 0.949(18) . ?
C20 H20 0.991(18) . ?
C21 C28 1.386(2) . ?
C21 H21 0.990(17) . ?
C22 C25 1.394(2) . ?
C22 H22 1.007(17) . ?
C23 C31 1.370(3) . ?
C23 H23 0.991(17) . ?
C24 H24A 1.004(18) . ?
C24 H24B 1.020(17) . ?
C24 H24C 1.018(18) . ?
C25 C26 1.371(3) . ?
C25 H25 0.96(2) . ?
C26 H26 1.005(17) . ?
C28 C29 1.376(3) . ?
C28 H28 0.97(2) . ?
C29 C31 1.368(3) . ?
C29 H29 0.94(2) . ?
C31 H31 0.97(2) . ?
C27A C28A 1.379(13) . ?
C27A C32A 1.398(15) . ?
C28A C29A 1.374(16) . ?
C28A H28A 0.9400 . ?
C29A C30A 1.384(9) . ?
C29A H29A 0.9400 . ?
C30A C31A 1.375(8) . ?
C30A H30A 0.9400 . ?
C31A C32A 1.387(9) . ?
C31A H31A 0.9400 . ?
C32A H32A 0.9400 . ?
C32B C31B 1.368(10) . ?
C32B C27B 1.402(18) . ?
C32B H32B 0.9400 . ?
C31B C30B 1.381(8) . ?
C31B H31B 0.9400 . ?
C30B C29B 1.375(10) . ?
C30B H30B 0.9400 . ?
C29B C28B 1.411(19) . ?
C29B H29B 0.9400 . ?
C28B C27B 1.384(14) . ?
C28B H28B 0.9400 . ?

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
C15 C3 C6 120.27(13) . . ?
C15 C3 C12 126.15(13) . . ?
C6 C3 C12 113.58(12) . . ?
C16 C4 C11 120.56(13) . . ?
C16 C4 C8 126.08(13) . . ?
C11 C4 C8 113.35(11) . . ?
C21 C5 C23 119.19(14) . . ?
C21 C5 C10 122.11(12) . . ?
C23 C5 C10 118.68(13) . . ?
C14 C6 C3 119.88(13) . . ?
C14 C6 C8 126.19(13) . . ?
C3 C6 C8 113.92(11) . . ?
C13 C7 C9 124.83(11) . . ?
C13 C7 C8 114.80(12) . . ?
C9 C7 C8 119.99(11) . . ?
C18 C8 C6 113.92(12) . . ?
C18 C8 C4 114.59(11) . . ?
C6 C8 C4 104.22(11) . . ?
C18 C8 C7 113.77(12) . . ?
C6 C8 C7 104.44(10) . . ?
C4 C8 C7 104.76(10) . . ?
O1 C9 C27B 116.7(7) . . ?
O1 C9 C7 118.56(13) . . ?
C27B C9 C7 124.7(7) . . ?
O1 C9 C27A 125.8(5) . . ?
C7 C9 C27A 115.6(5) . . ?
O2 C10 C5 121.86(12) . . ?
O2 C10 C13 119.39(12) . . ?
C5 C10 C13 118.70(11) . . ?
C22 C11 C4 119.92(13) . . ?
C22 C11 C12 126.00(13) . . ?
C4 C11 C12 114.06(12) . . ?
C24 C12 C3 114.13(12) . . ?
C24 C12 C11 114.50(12) . . ?
C3 C12 C11 104.63(10) . . ?
C24 C12 C13 113.87(11) . . ?
C3 C12 C13 103.91(11) . . ?
C11 C12 C13 104.63(10) . . ?
C7 C13 C10 126.14(12) . . ?
C7 C13 C12 115.04(11) . . ?
C10 C13 C12 118.81(11) . . ?
C6 C14 C19 119.34(15) . . ?
C6 C14 H14 119.7(9) . . ?
C19 C14 H14 120.9(9) . . ?
C3 C15 C20 119.52(15) . . ?
C3 C15 H15 118.8(9) . . ?
C20 C15 H15 121.7(9) . . ?
C4 C16 C26 119.01(16) . . ?
C4 C16 H16 120.6(9) . . ?
C26 C16 H16 120.4(9) . . ?
C8 C18 H18A 111.8(9) . . ?
C8 C18 H18B 110.3(9) . . ?
H18A C18 H18B 107.3(13) . . ?
C8 C18 H18C 111.1(9) . . ?
H18A C18 H18C 107.9(12) . . ?
H18B C18 H18C 108.3(13) . . ?
C20 C19 C14 120.64(15) . . ?
C20 C19 H19 121.6(10) . . ?
C14 C19 H19 117.8(10) . . ?
C19 C20 C15 120.35(15) . . ?
C19 C20 H20 119.1(10) . . ?
C15 C20 H20 120.6(10) . . ?
C5 C21 C28 119.92(15) . . ?
C5 C21 H21 119.6(9) . . ?
C28 C21 H21 120.4(10) . . ?
C11 C22 C25 119.18(16) . . ?
C11 C22 H22 120.1(9) . . ?
C25 C22 H22 120.7(9) . . ?
C31 C23 C5 120.16(17) . . ?
C31 C23 H23 122.2(10) . . ?
C5 C23 H23 117.6(10) . . ?
C12 C24 H24A 108.4(9) . . ?
C12 C24 H24B 112.4(10) . . ?
H24A C24 H24B 107.2(13) . . ?
C12 C24 H24C 110.4(9) . . ?
H24A C24 H24C 108.8(14) . . ?
H24B C24 H24C 109.5(13) . . ?
C26 C25 C22 120.83(16) . . ?
C26 C25 H25 119.7(11) . . ?
C22 C25 H25 119.5(11) . . ?
C25 C26 C16 120.49(16) . . ?
C25 C26 H26 121.9(10) . . ?
C16 C26 H26 117.6(10) . . ?
C29 C28 C21 119.93(19) . . ?
C29 C28 H28 120.4(13) . . ?
C21 C28 H28 119.7(13) . . ?
C31 C29 C28 120.36(18) . . ?
C31 C29 H29 120.6(13) . . ?
C28 C29 H29 119.1(13) . . ?
C29 C31 C23 120.41(17) . . ?
C29 C31 H31 118.2(12) . . ?
C23 C31 H31 121.4(12) . . ?
C28A C27A C32A 119.3(10) . . ?
C28A C27A C9 121.7(10) . . ?
C32A C27A C9 119.0(10) . . ?
C29A C28A C27A 120.1(10) . . ?
C29A C28A H28A 120.0 . . ?
C27A C28A H28A 120.0 . . ?
C28A C29A C30A 120.4(8) . . ?
C28A C29A H29A 119.8 . . ?
C30A C29A H29A 119.8 . . ?
C31A C30A C29A 120.6(8) . . ?
C31A C30A H30A 119.7 . . ?
C29A C30A H30A 119.7 . . ?
C30A C31A C32A 119.0(7) . . ?
C30A C31A H31A 120.5 . . ?
C32A C31A H31A 120.5 . . ?
C31A C32A C27A 120.6(7) . . ?
C31A C32A H32A 119.7 . . ?
C27A C32A H32A 119.7 . . ?
C31B C32B C27B 120.5(8) . . ?
C31B C32B H32B 119.8 . . ?
C27B C32B H32B 119.8 . . ?
C32B C31B C30B 120.4(8) . . ?
C32B C31B H31B 119.8 . . ?
C30B C31B H31B 119.8 . . ?
C29B C30B C31B 121.3(8) . . ?
C29B C30B H30B 119.3 . . ?
C31B C30B H30B 119.3 . . ?
C30B C29B C28B 117.8(8) . . ?
C30B C29B H29B 121.1 . . ?
C28B C29B H29B 121.1 . . ?
C27B C28B C29B 121.7(11) . . ?
C27B C28B H28B 119.1 . . ?
C29B C28B H28B 119.1 . . ?
C28B C27B C9 120.7(13) . . ?
C28B C27B C32B 118.2(13) . . ?
C9 C27B C32B 121.1(11) . . ?

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
C15 C3 C6 C14 0.40(19) . . . . ?
C12 C3 C6 C14 -179.03(11) . . . . ?
C15 C3 C6 C8 179.79(12) . . . . ?
C12 C3 C6 C8 0.36(15) . . . . ?
C14 C6 C8 C18 -2.30(18) . . . . ?
C3 C6 C8 C18 178.36(11) . . . . ?
C14 C6 C8 C4 123.30(13) . . . . ?
C3 C6 C8 C4 -56.04(13) . . . . ?
C14 C6 C8 C7 -127.02(13) . . . . ?
C3 C6 C8 C7 53.64(14) . . . . ?
C16 C4 C8 C18 2.5(2) . . . . ?
C11 C4 C8 C18 -178.75(12) . . . . ?
C16 C4 C8 C6 -122.68(14) . . . . ?
C11 C4 C8 C6 56.08(14) . . . . ?
C16 C4 C8 C7 127.88(14) . . . . ?
C11 C4 C8 C7 -53.36(14) . . . . ?
C13 C7 C8 C18 -178.44(12) . . . . ?
C9 C7 C8 C18 8.26(17) . . . . ?
C13 C7 C8 C6 -53.63(14) . . . . ?
C9 C7 C8 C6 133.08(13) . . . . ?
C13 C7 C8 C4 55.66(14) . . . . ?
C9 C7 C8 C4 -117.64(13) . . . . ?
C13 C7 C9 O1 -102.66(16) . . . . ?
C8 C7 C9 O1 69.92(17) . . . . ?
C13 C7 C9 C27B 77.9(10) . . . . ?
C8 C7 C9 C27B -109.5(10) . . . . ?
C13 C7 C9 C27A 78.0(7) . . . . ?
C8 C7 C9 C27A -109.4(7) . . . . ?
C21 C5 C10 O2 167.12(15) . . . . ?
C23 C5 C10 O2 -11.5(2) . . . . ?
C21 C5 C10 C13 -15.3(2) . . . . ?
C23 C5 C10 C13 166.09(13) . . . . ?
C16 C4 C11 C22 -0.6(2) . . . . ?
C8 C4 C11 C22 -179.44(13) . . . . ?
C16 C4 C11 C12 177.91(12) . . . . ?
C8 C4 C11 C12 -0.92(16) . . . . ?
C15 C3 C12 C24 1.43(19) . . . . ?
C6 C3 C12 C24 -179.18(12) . . . . ?
C15 C3 C12 C11 -124.49(14) . . . . ?
C6 C3 C12 C11 54.91(14) . . . . ?
C15 C3 C12 C13 126.03(14) . . . . ?
C6 C3 C12 C13 -54.58(13) . . . . ?
C22 C11 C12 C24 -2.1(2) . . . . ?
C4 C11 C12 C24 179.52(13) . . . . ?
C22 C11 C12 C3 123.62(15) . . . . ?
C4 C11 C12 C3 -54.80(15) . . . . ?
C22 C11 C12 C13 -127.42(15) . . . . ?
C4 C11 C12 C13 54.16(14) . . . . ?
C9 C7 C13 C10 -8.7(2) . . . . ?
C8 C7 C13 C10 178.38(12) . . . . ?
C9 C7 C13 C12 171.47(12) . . . . ?
C8 C7 C13 C12 -1.45(16) . . . . ?
O2 C10 C13 C7 -91.08(18) . . . . ?
C5 C10 C13 C7 91.28(17) . . . . ?
O2 C10 C13 C12 88.74(17) . . . . ?
C5 C10 C13 C12 -88.90(15) . . . . ?
C24 C12 C13 C7 -179.14(13) . . . . ?
C3 C12 C13 C7 56.10(14) . . . . ?
C11 C12 C13 C7 -53.39(15) . . . . ?
C24 C12 C13 C10 1.01(18) . . . . ?
C3 C12 C13 C10 -123.75(12) . . . . ?
C11 C12 C13 C10 126.76(12) . . . . ?
C3 C6 C14 C19 0.06(19) . . . . ?
C8 C6 C14 C19 -179.24(12) . . . . ?
C6 C3 C15 C20 -0.6(2) . . . . ?
C12 C3 C15 C20 178.77(12) . . . . ?
C11 C4 C16 C26 0.2(2) . . . . ?
C8 C4 C16 C26 178.83(14) . . . . ?
C6 C14 C19 C20 -0.3(2) . . . . ?
C14 C19 C20 C15 0.2(2) . . . . ?
C3 C15 C20 C19 0.3(2) . . . . ?
C23 C5 C21 C28 1.4(2) . . . . ?
C10 C5 C21 C28 -177.22(16) . . . . ?
C4 C11 C22 C25 0.6(2) . . . . ?
C12 C11 C22 C25 -177.78(14) . . . . ?
C21 C5 C23 C31 -0.4(2) . . . . ?
C10 C5 C23 C31 178.23(15) . . . . ?
C11 C22 C25 C26 -0.1(3) . . . . ?
C22 C25 C26 C16 -0.4(3) . . . . ?
C4 C16 C26 C25 0.3(3) . . . . ?
C5 C21 C28 C29 -1.0(3) . . . . ?
C21 C28 C29 C31 -0.3(3) . . . . ?
C28 C29 C31 C23 1.3(3) . . . . ?
C5 C23 C31 C29 -0.9(3) . . . . ?
O1 C9 C27A C28A -173.6(9) . . . . ?
C7 C9 C27A C28A 5.7(16) . . . . ?
O1 C9 C27A C32A 7.4(17) . . . . ?
C7 C9 C27A C32A -173.3(10) . . . . ?
C32A C27A C28A C29A -2(2) . . . . ?
C9 C27A C28A C29A 178.4(13) . . . . ?
C27A C28A C29A C30A 2.9(19) . . . . ?
C28A C29A C30A C31A -1.6(16) . . . . ?
C29A C30A C31A C32A -0.1(13) . . . . ?
C30A C31A C32A C27A 0.4(15) . . . . ?
C28A C27A C32A C31A 0.9(19) . . . . ?
C9 C27A C32A C31A 179.9(10) . . . . ?
C27B C32B C31B C30B 3.5(17) . . . . ?
C32B C31B C30B C29B -1.9(15) . . . . ?
C31B C30B C29B C28B 0.5(18) . . . . ?
C30B C29B C28B C27B -1(2) . . . . ?
C29B C28B C27B C9 -178.5(16) . . . . ?
C29B C28B C27B C32B 2(2) . . . . ?
O1 C9 C27B C28B -172.3(12) . . . . ?
C7 C9 C27B C28B 7(2) . . . . ?
O1 C9 C27B C32B 6.9(19) . . . . ?
C7 C9 C27B C32B -173.7(10) . . . . ?
C31B C32B C27B C28B -4(2) . . . . ?
C31B C32B C27B C9 177.2(12) . . . . ?

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

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

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_dibenzobarrelene_beforeUV
_database_code_depnum_ccdc_archive 'CCDC 1860421'
_audit_update_record             
;
2018-08-06 deposited with the CCDC.
2018-10-02 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C32 H24 O2'
_chemical_formula_moiety         'C32 H24 O2'
_chemical_formula_weight         440.54
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.2215(10)
_cell_length_b                   10.1283(10)
_cell_length_c                   14.3122(16)
_cell_angle_alpha                102.715(6)
_cell_angle_beta                 99.297(8)
_cell_angle_gamma                111.851(6)
_cell_volume                     1165.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4042
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      68.16
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464.00
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_T_max  0.942

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

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            9968
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_theta_max         68.213
_diffrn_reflns_theta_min         3.287
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.948
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             4009
_reflns_number_gt                2587
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# 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          0.0934
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1580
_refine_ls_wR_factor_gt          0.1234
_refine_ls_number_restraints     72
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         4009
_refine_ls_number_parameters     362
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0623P)²+0.3037P] 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         0.23
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 0.2547(2) -0.20503(19) 0.35031(14) 0.0592(5) Uani 1 1 d . . . . .
O2 O -0.0034(2) -0.1506(2) 0.06698(13) 0.0624(5) Uani 1 1 d . . . . .
C1 C 0.3288(3) 0.2556(2) 0.33595(17) 0.0359(6) Uani 1 1 d . . . . .
C2 C 0.2983(3) 0.3604(3) 0.39868(19) 0.0434(6) Uani 1 1 d . . . . .
H2 H 0.3056 0.3634 0.4655 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2566(3) 0.4615(3) 0.3624(2) 0.0504(7) Uani 1 1 d . . . . .
H3 H 0.2360 0.5335 0.4050 0.060 Uiso 1 1 calc R U . . .
C4 C 0.2451(3) 0.4571(3) 0.2647(2) 0.0508(7) Uani 1 1 d . . . . .
H4 H 0.2168 0.5261 0.2409 0.061 Uiso 1 1 calc R U . . .
C5 C 0.2749(3) 0.3520(3) 0.20112(19) 0.0460(6) Uani 1 1 d . . . . .
H5 H 0.2658 0.3488 0.1342 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3181(3) 0.2514(2) 0.23644(16) 0.0358(6) Uani 1 1 d . . . . .
C7 C 0.3589(3) 0.1312(2) 0.17699(16) 0.0374(6) Uani 1 1 d . . . . .
C8 C 0.3447(3) 0.1248(3) 0.06843(17) 0.0502(7) Uani 1 1 d . . . . .
H8A H 0.3722 0.0464 0.0355 0.060 Uiso 1 1 calc R U . . .
H8B H 0.2344 0.1040 0.0358 0.060 Uiso 1 1 calc R U . . .
H8C H 0.4186 0.2200 0.0648 0.060 Uiso 1 1 calc R U . . .
C9 C 0.5282(3) 0.1624(2) 0.23673(17) 0.0367(6) Uani 1 1 d . . . . .
C10 C 0.6628(3) 0.1874(3) 0.2015(2) 0.0506(7) Uani 1 1 d . . . . .
H10 H 0.6555 0.1834 0.1345 0.061 Uiso 1 1 calc R U . . .
C11 C 0.8106(3) 0.2187(3) 0.2657(2) 0.0622(8) Uani 1 1 d . . . . .
H11 H 0.9031 0.2355 0.2419 0.075 Uiso 1 1 calc R U . . .
C12 C 0.8217(3) 0.2249(3) 0.3633(2) 0.0594(8) Uani 1 1 d . . . . .
H12 H 0.9221 0.2471 0.4062 0.071 Uiso 1 1 calc R U . . .
C13 C 0.6860(3) 0.1987(3) 0.39968(19) 0.0465(6) Uani 1 1 d . . . . .
H13 H 0.6939 0.2028 0.4667 0.056 Uiso 1 1 calc R U . . .
C14 C 0.5391(3) 0.1667(2) 0.33603(17) 0.0364(6) Uani 1 1 d . . . . .
C15 C 0.3787(3) 0.1374(2) 0.36378(16) 0.0334(5) Uani 1 1 d . . . . .
C16 C 0.3863(3) 0.1392(3) 0.47082(16) 0.0446(6) Uani 1 1 d . . . . .
H16A H 0.2803 0.1198 0.4820 0.053 Uiso 1 1 calc R U . . .
H16B H 0.4187 0.0627 0.4837 0.053 Uiso 1 1 calc R U . . .
H16C H 0.4648 0.2363 0.5152 0.053 Uiso 1 1 calc R U . . .
C17 C 0.2426(3) -0.0149(2) 0.19196(16) 0.0334(5) Uani 1 1 d . . . . .
C18 C 0.1315(3) -0.1421(3) 0.10179(17) 0.0389(6) Uani 1 1 d . . . . .
C19 C 0.1873(3) -0.2528(2) 0.05556(16) 0.0391(6) Uani 1 1 d . . . . .
C20 C 0.3246(3) -0.2621(3) 0.10389(19) 0.0499(7) Uani 1 1 d . . . . .
H20 H 0.3872 -0.1943 0.1670 0.060 Uiso 1 1 calc R U . . .
C21 C 0.3690(4) -0.3712(3) 0.0592(2) 0.0651(8) Uani 1 1 d . . . . .
H21 H 0.4605 -0.3790 0.0927 0.078 Uiso 1 1 calc R U . . .
C22 C 0.2802(4) -0.4682(3) -0.0340(2) 0.0679(9) Uani 1 1 d . . . . .
H22 H 0.3112 -0.5420 -0.0641 0.082 Uiso 1 1 calc R U . . .
C23 C 0.1464(4) -0.4576(3) -0.0831(2) 0.0645(9) Uani 1 1 d . . . . .
H23 H 0.0866 -0.5237 -0.1471 0.077 Uiso 1 1 calc R U . . .
C24 C 0.0994(3) -0.3515(3) -0.03946(18) 0.0503(7) Uani 1 1 d . . . . .
H24 H 0.0075 -0.3450 -0.0736 0.060 Uiso 1 1 calc R U . . .
C25 C 0.2546(3) -0.0116(2) 0.28609(16) 0.0340(5) Uani 1 1 d . . . . .
C26 C 0.1731(3) -0.1445(3) 0.31917(16) 0.0385(6) Uani 1 1 d . . . . .
C27A C -0.018(3) -0.195(3) 0.313(3) 0.034(3) Uani 0.43(3) 1 d . U P A 1
C28A C -0.087(3) -0.102(2) 0.284(2) 0.043(3) Uani 0.43(3) 1 d . U P A 1
H28A H -0.0256 -0.0149 0.2700 0.051 Uiso 0.43(3) 1 calc R U P A 1
C29A C -0.2512(18) -0.147(2) 0.2772(13) 0.051(3) Uani 0.43(3) 1 d . U P A 1
H29A H -0.3021 -0.0878 0.2596 0.061 Uiso 0.43(3) 1 calc R U P A 1
C30A C -0.343(2) -0.2799(19) 0.2963(10) 0.047(3) Uani 0.43(3) 1 d . U P A 1
H30A H -0.4542 -0.3069 0.2914 0.057 Uiso 0.43(3) 1 calc R U P A 1
C31A C -0.272(2) -0.3726(15) 0.3227(9) 0.043(3) Uani 0.43(3) 1 d . U P A 1
H31A H -0.3330 -0.4613 0.3354 0.051 Uiso 0.43(3) 1 calc R U P A 1
C32A C -0.106(2) -0.325(2) 0.3290(14) 0.045(3) Uani 0.43(3) 1 d . U P A 1
H32A H -0.0543 -0.3851 0.3447 0.054 Uiso 0.43(3) 1 calc R U P A 1
C27B C 0.013(2) -0.201(3) 0.315(2) 0.040(3) Uani 0.57(3) 1 d . U P A 2
C28B C -0.088(2) -0.134(2) 0.2931(15) 0.051(3) Uani 0.57(3) 1 d . U P A 2
H28B H -0.0430 -0.0430 0.2786 0.061 Uiso 0.57(3) 1 calc R U P A 2
C29B C -0.2531(17) -0.1915(19) 0.2906(10) 0.061(3) Uani 0.57(3) 1 d . U P A 2
H29B H -0.3178 -0.1417 0.2757 0.073 Uiso 0.57(3) 1 calc R U P A 2
C30B C -0.3141(13) -0.3224(16) 0.3107(8) 0.055(3) Uani 0.57(3) 1 d . U P A 2
H30B H -0.4249 -0.3663 0.3077 0.066 Uiso 0.57(3) 1 calc R U P A 2
C31B C -0.2206(19) -0.3932(15) 0.3354(9) 0.057(3) Uani 0.57(3) 1 d . U P A 2
H31B H -0.2681 -0.4840 0.3490 0.068 Uiso 0.57(3) 1 calc R U P A 2
C32B C -0.0595(17) -0.3345(15) 0.3406(11) 0.045(2) Uani 0.57(3) 1 d . U P A 2
H32B H 0.0041 -0.3824 0.3609 0.054 Uiso 0.57(3) 1 calc R U P A 2


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXD Version 2013/2 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'

#==============================================================================
# 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 C26 1.223(3) . ?
O2 C18 1.226(3) . ?
C1 C2 1.377(3) . ?
C1 C6 1.402(3) . ?
C1 C15 1.537(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.529(3) . ?
C7 C8 1.523(3) . ?
C7 C9 1.533(3) . ?
C7 C17 1.555(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 C10 1.373(3) . ?
C9 C14 1.398(3) . ?
C10 C11 1.396(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.370(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.390(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.533(3) . ?
C15 C16 1.518(3) . ?
C15 C25 1.545(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 C25 1.326(3) . ?
C17 C18 1.494(3) . ?
C18 C19 1.474(3) . ?
C19 C20 1.387(3) . ?
C19 C24 1.396(3) . ?
C20 C21 1.382(4) . ?
C20 H20 0.9400 . ?
C21 C22 1.373(4) . ?
C21 H21 0.9400 . ?
C22 C23 1.371(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.368(4) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?
C25 C26 1.497(3) . ?
C26 C27B 1.357(19) . ?
C26 C27A 1.62(2) . ?
C27A C32A 1.36(3) . ?
C27A C28A 1.41(2) . ?
C28A C29A 1.39(2) . ?
C28A H28A 0.9400 . ?
C29A C30A 1.411(14) . ?
C29A H29A 0.9400 . ?
C30A C31A 1.410(13) . ?
C30A H30A 0.9400 . ?
C31A C32A 1.409(16) . ?
C31A H31A 0.9400 . ?
C32A H32A 0.9400 . ?
C27B C28B 1.382(17) . ?
C27B C32B 1.42(2) . ?
C28B C29B 1.406(19) . ?
C28B H28B 0.9400 . ?
C29B C30B 1.351(11) . ?
C29B H29B 0.9400 . ?
C30B C31B 1.361(10) . ?
C30B H30B 0.9400 . ?
C31B C32B 1.361(13) . ?
C31B H31B 0.9400 . ?
C32B H32B 0.9400 . ?

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 C1 C6 120.2(2) . . ?
C2 C1 C15 126.3(2) . . ?
C6 C1 C15 113.49(19) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 126.3(2) . . ?
C1 C6 C7 113.95(19) . . ?
C8 C7 C6 114.06(19) . . ?
C8 C7 C9 114.5(2) . . ?
C6 C7 C9 104.55(18) . . ?
C8 C7 C17 114.00(19) . . ?
C6 C7 C17 103.58(18) . . ?
C9 C7 C17 104.96(17) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 120.1(2) . . ?
C10 C9 C7 126.0(2) . . ?
C14 C9 C7 113.9(2) . . ?
C9 C10 C11 119.5(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.1(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C9 120.3(2) . . ?
C13 C14 C15 126.0(2) . . ?
C9 C14 C15 113.6(2) . . ?
C16 C15 C14 114.84(19) . . ?
C16 C15 C1 113.54(19) . . ?
C14 C15 C1 104.22(17) . . ?
C16 C15 C25 114.03(18) . . ?
C14 C15 C25 104.88(17) . . ?
C1 C15 C25 104.17(17) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C25 C17 C18 127.0(2) . . ?
C25 C17 C7 114.71(19) . . ?
C18 C17 C7 118.32(18) . . ?
O2 C18 C19 121.5(2) . . ?
O2 C18 C17 119.1(2) . . ?
C19 C18 C17 119.4(2) . . ?
C20 C19 C24 119.0(2) . . ?
C20 C19 C18 121.9(2) . . ?
C24 C19 C18 119.2(2) . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 120.3(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 120.3(3) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C17 C25 C26 124.5(2) . . ?
C17 C25 C15 115.25(19) . . ?
C26 C25 C15 119.78(18) . . ?
O1 C26 C27B 118.7(10) . . ?
O1 C26 C25 118.3(2) . . ?
C27B C26 C25 123.0(10) . . ?
O1 C26 C27A 125.0(10) . . ?
C25 C26 C27A 116.7(10) . . ?
C32A C27A C28A 123.1(16) . . ?
C32A C27A C26 120.2(17) . . ?
C28A C27A C26 117(2) . . ?
C29A C28A C27A 116.2(15) . . ?
C29A C28A H28A 121.9 . . ?
C27A C28A H28A 121.9 . . ?
C28A C29A C30A 121.5(11) . . ?
C28A C29A H29A 119.2 . . ?
C30A C29A H29A 119.2 . . ?
C31A C30A C29A 121.2(11) . . ?
C31A C30A H30A 119.4 . . ?
C29A C30A H30A 119.4 . . ?
C32A C31A C30A 116.5(11) . . ?
C32A C31A H31A 121.8 . . ?
C30A C31A H31A 121.8 . . ?
C27A C32A C31A 121.4(13) . . ?
C27A C32A H32A 119.3 . . ?
C31A C32A H32A 119.3 . . ?
C26 C27B C28B 124.4(18) . . ?
C26 C27B C32B 120.1(13) . . ?
C28B C27B C32B 115.5(13) . . ?
C27B C28B C29B 124.2(12) . . ?
C27B C28B H28B 117.9 . . ?
C29B C28B H28B 117.9 . . ?
C30B C29B C28B 116.4(9) . . ?
C30B C29B H29B 121.8 . . ?
C28B C29B H29B 121.8 . . ?
C29B C30B C31B 122.3(9) . . ?
C29B C30B H30B 118.8 . . ?
C31B C30B H30B 118.8 . . ?
C32B C31B C30B 121.1(10) . . ?
C32B C31B H31B 119.5 . . ?
C30B C31B H31B 119.5 . . ?
C31B C32B C27B 120.4(10) . . ?
C31B C32B H32B 119.8 . . ?
C27B C32B H32B 119.8 . . ?

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
C6 C1 C2 C3 0.1(3) . . . . ?
C15 C1 C2 C3 179.0(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
C15 C1 C6 C5 -179.8(2) . . . . ?
C2 C1 C6 C7 178.8(2) . . . . ?
C15 C1 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 -1.4(3) . . . . ?
C1 C6 C7 C8 179.1(2) . . . . ?
C5 C6 C7 C9 124.4(2) . . . . ?
C1 C6 C7 C9 -55.1(2) . . . . ?
C5 C6 C7 C17 -125.9(2) . . . . ?
C1 C6 C7 C17 54.6(2) . . . . ?
C8 C7 C9 C10 1.5(3) . . . . ?
C6 C7 C9 C10 -124.0(2) . . . . ?
C17 C7 C9 C10 127.3(2) . . . . ?
C8 C7 C9 C14 -179.48(19) . . . . ?
C6 C7 C9 C14 55.0(2) . . . . ?
C17 C7 C9 C14 -53.7(2) . . . . ?
C14 C9 C10 C11 -0.8(4) . . . . ?
C7 C9 C10 C11 178.2(2) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C9 -0.7(4) . . . . ?
C12 C13 C14 C15 -179.0(2) . . . . ?
C10 C9 C14 C13 1.2(3) . . . . ?
C7 C9 C14 C13 -177.8(2) . . . . ?
C10 C9 C14 C15 179.7(2) . . . . ?
C7 C9 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 -2.4(3) . . . . ?
C9 C14 C15 C16 179.21(19) . . . . ?
C13 C14 C15 C1 122.4(2) . . . . ?
C9 C14 C15 C1 -55.9(2) . . . . ?
C13 C14 C15 C25 -128.4(2) . . . . ?
C9 C14 C15 C25 53.2(2) . . . . ?
C2 C1 C15 C16 2.5(3) . . . . ?
C6 C1 C15 C16 -178.57(19) . . . . ?
C2 C1 C15 C14 -123.2(2) . . . . ?
C6 C1 C15 C14 55.8(2) . . . . ?
C2 C1 C15 C25 127.1(2) . . . . ?
C6 C1 C15 C25 -54.0(2) . . . . ?
C8 C7 C17 C25 179.4(2) . . . . ?
C6 C7 C17 C25 -56.1(2) . . . . ?
C9 C7 C17 C25 53.3(2) . . . . ?
C8 C7 C17 C18 -0.5(3) . . . . ?
C6 C7 C17 C18 124.0(2) . . . . ?
C9 C7 C17 C18 -126.6(2) . . . . ?
C25 C17 C18 O2 90.4(3) . . . . ?
C7 C17 C18 O2 -89.7(3) . . . . ?
C25 C17 C18 C19 -90.7(3) . . . . ?
C7 C17 C18 C19 89.1(3) . . . . ?
O2 C18 C19 C20 -167.2(2) . . . . ?
C17 C18 C19 C20 14.0(3) . . . . ?
O2 C18 C19 C24 12.6(3) . . . . ?
C17 C18 C19 C24 -166.2(2) . . . . ?
C24 C19 C20 C21 -2.2(4) . . . . ?
C18 C19 C20 C21 177.7(2) . . . . ?
C19 C20 C21 C22 1.6(4) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C22 C23 C24 C19 0.0(4) . . . . ?
C20 C19 C24 C23 1.4(4) . . . . ?
C18 C19 C24 C23 -178.5(2) . . . . ?
C18 C17 C25 C26 8.8(4) . . . . ?
C7 C17 C25 C26 -171.1(2) . . . . ?
C18 C17 C25 C15 -178.8(2) . . . . ?
C7 C17 C25 C15 1.3(3) . . . . ?
C16 C15 C25 C17 178.4(2) . . . . ?
C14 C15 C25 C17 -55.2(2) . . . . ?
C1 C15 C25 C17 54.1(2) . . . . ?
C16 C15 C25 C26 -8.8(3) . . . . ?
C14 C15 C25 C26 117.6(2) . . . . ?
C1 C15 C25 C26 -133.1(2) . . . . ?
C17 C25 C26 O1 102.3(3) . . . . ?
C15 C25 C26 O1 -69.8(3) . . . . ?
C17 C25 C26 C27B -77.2(13) . . . . ?
C15 C25 C26 C27B 110.7(13) . . . . ?
C17 C25 C26 C27A -78.9(14) . . . . ?
C15 C25 C26 C27A 109.0(14) . . . . ?
O1 C26 C27A C32A -10(3) . . . . ?
C25 C26 C27A C32A 171.4(19) . . . . ?
O1 C26 C27A C28A 173.9(14) . . . . ?
C25 C26 C27A C28A -5(2) . . . . ?
C32A C27A C28A C29A 3(3) . . . . ?
C26 C27A C28A C29A 179(2) . . . . ?
C27A C28A C29A C30A -1(3) . . . . ?
C28A C29A C30A C31A 0(2) . . . . ?
C29A C30A C31A C32A 0.1(18) . . . . ?
C28A C27A C32A C31A -3(4) . . . . ?
C26 C27A C32A C31A -179.2(18) . . . . ?
C30A C31A C32A C27A 2(3) . . . . ?
O1 C26 C27B C28B 172.1(14) . . . . ?
C25 C26 C27B C28B -8(3) . . . . ?
O1 C26 C27B C32B -5(3) . . . . ?
C25 C26 C27B C32B 175.0(13) . . . . ?
C26 C27B C28B C29B -179(2) . . . . ?
C32B C27B C28B C29B -2(3) . . . . ?
C27B C28B C29B C30B -1(2) . . . . ?
C28B C29B C30B C31B 2.1(17) . . . . ?
C29B C30B C31B C32B -0.2(15) . . . . ?
C30B C31B C32B C27B -3.1(19) . . . . ?
C26 C27B C32B C31B -178.9(15) . . . . ?
C28B C27B C32B C31B 4(2) . . . . ?

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

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


