# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1442077'
_audit_update_record             
;
2015-12-12 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        BSPAnt
_chemical_name_common            ?
_chemical_melting_point          370
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 S2'
_chemical_formula_weight         422.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0345(3)
_cell_length_b                   7.6843(4)
_cell_length_c                   22.6054(16)
_cell_angle_alpha                92.827(7)
_cell_angle_beta                 96.554(7)
_cell_angle_gamma                90.103(6)
_cell_volume                     1040.09(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9302
_cell_measurement_theta_min      6.80
_cell_measurement_theta_max      68.30

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.398
_shelx_estimated_absorpt_T_min   0.646
_shelx_estimated_absorpt_T_max   0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_T_max  0.619
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12839
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         6.826
_diffrn_reflns_theta_max         68.328
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             3633
_reflns_number_gt                2615
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1554P)²+1.6342P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.047(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3633
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0952
_refine_ls_wR_factor_ref         0.2984
_refine_ls_wR_factor_gt          0.2718
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
S1 S 0.5171(3) 0.4198(2) 0.07539(6) 0.0594(6) Uani 1 1 d . . . . .
S2 S 0.0219(3) -0.0237(2) 0.07513(6) 0.0621(6) Uani 1 1 d . . . . .
C1 C 0.2547(12) 0.5257(14) 0.0717(3) 0.092(3) Uani 1 1 d . . . . .
H1A H 0.1649 0.4750 0.0988 0.138 Uiso 1 1 calc R U . . .
H1B H 0.1804 0.5118 0.0318 0.138 Uiso 1 1 calc R U . . .
H1C H 0.2771 0.6474 0.0823 0.138 Uiso 1 1 calc R U . . .
C2 C 0.6267(8) 0.4495(7) 0.1507(2) 0.0438(11) Uani 1 1 d . . . . .
C3 C 0.8189(9) 0.3570(8) 0.1681(2) 0.0510(13) Uani 1 1 d . . . . .
H3 H 0.8818 0.2863 0.1400 0.061 Uiso 1 1 calc R U . . .
C4 C 0.9183(8) 0.3682(7) 0.2263(2) 0.0490(12) Uani 1 1 d . . . . .
H4 H 1.0458 0.3036 0.2367 0.059 Uiso 1 1 calc R U . . .
C5 C 0.8317(7) 0.4744(6) 0.2701(2) 0.0374(10) Uani 1 1 d . . . . .
C6 C 0.9351(7) 0.4792(6) 0.3331(2) 0.0372(10) Uani 1 1 d . . . . .
C7 C 1.1554(7) 0.4139(6) 0.3475(2) 0.0396(10) Uani 1 1 d . . . . .
H7 H 1.2387 0.3810 0.3167 0.047 Uiso 1 1 calc R U . . .
C8 C 1.2465(7) 0.3985(6) 0.4047(2) 0.0388(10) Uani 1 1 d . . . . .
H8 H 1.3900 0.3546 0.4121 0.047 Uiso 1 1 calc R U . . .
C9 C 1.1265(7) 0.4484(6) 0.4539(2) 0.0354(10) Uani 1 1 d . . . . .
C10 C 1.2113(7) 0.4270(6) 0.5123(2) 0.0373(10) Uani 1 1 d . . . . .
H10 H 1.3513 0.3775 0.5205 0.045 Uiso 1 1 calc R U . . .
C11 C 0.9091(7) 0.5219(6) 0.4402(2) 0.0337(10) Uani 1 1 d . . . . .
C12 C 0.8197(7) 0.5341(6) 0.3794(2) 0.0396(11) Uani 1 1 d . . . . .
H12 H 0.6784 0.5809 0.3709 0.048 Uiso 1 1 calc R U . . .
C13 C 0.6410(9) 0.5671(7) 0.2517(2) 0.0481(12) Uani 1 1 d . . . . .
H13 H 0.5795 0.6397 0.2796 0.058 Uiso 1 1 calc R U . . .
C14 C 0.5395(9) 0.5563(8) 0.1942(2) 0.0521(13) Uani 1 1 d . . . . .
H14 H 0.4115 0.6206 0.1840 0.062 Uiso 1 1 calc R U . . .
C15 C -0.2388(12) -0.1280(13) 0.0688(3) 0.089(2) Uani 1 1 d . . . . .
H15A H -0.2181 -0.2518 0.0694 0.133 Uiso 1 1 calc R U . . .
H15B H -0.3232 -0.1002 0.0319 0.133 Uiso 1 1 calc R U . . .
H15C H -0.3177 -0.0893 0.1015 0.133 Uiso 1 1 calc R U . . .
C16 C 0.1282(8) -0.0359(7) 0.1504(2) 0.0446(11) Uani 1 1 d . . . . .
C17 C 0.3225(9) 0.0596(7) 0.1688(2) 0.0502(12) Uani 1 1 d . . . . .
H17 H 0.3880 0.1225 0.1412 0.060 Uiso 1 1 calc R U . . .
C18 C 0.4200(8) 0.0630(7) 0.2271(2) 0.0464(12) Uani 1 1 d . . . . .
H18 H 0.5485 0.1295 0.2379 0.056 Uiso 1 1 calc R U . . .
C19 C 0.3308(7) -0.0307(6) 0.2704(2) 0.0373(10) Uani 1 1 d . . . . .
C20 C 0.4346(7) -0.0202(6) 0.33330(19) 0.0364(10) Uani 1 1 d . . . . .
C21 C 0.3198(7) -0.0648(6) 0.3790(2) 0.0359(10) Uani 1 1 d . . . . .
H21 H 0.1789 -0.1151 0.3701 0.043 Uiso 1 1 calc R U . . .
C22 C 0.4089(7) -0.0369(6) 0.44028(19) 0.0327(9) Uani 1 1 d . . . . .
C23 C 0.2881(7) -0.0756(6) 0.4871(2) 0.0375(10) Uani 1 1 d . . . . .
H23 H 0.1478 -0.1272 0.4787 0.045 Uiso 1 1 calc R U . . .
C24 C 0.6261(7) 0.0382(5) 0.45405(19) 0.0332(9) Uani 1 1 d . . . . .
C25 C 0.1369(8) -0.1275(7) 0.2511(2) 0.0453(12) Uani 1 1 d . . . . .
H25 H 0.0731 -0.1921 0.2786 0.054 Uiso 1 1 calc R U . . .
C26 C 0.0363(9) -0.1311(8) 0.1929(2) 0.0510(13) Uani 1 1 d . . . . .
H26 H -0.0927 -0.1969 0.1820 0.061 Uiso 1 1 calc R U . . .
C27 C 0.7467(7) 0.0773(6) 0.4050(2) 0.0398(10) Uani 1 1 d . . . . .
H27 H 0.8903 0.1233 0.4127 0.048 Uiso 1 1 calc R U . . .
C28 C 0.6557(7) 0.0487(7) 0.3479(2) 0.0415(11) Uani 1 1 d . . . . .
H28 H 0.7391 0.0744 0.3173 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.757(5) . ?
S1 C1 1.777(7) . ?
S2 C15 1.752(8) . ?
S2 C16 1.755(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.390(7) . ?
C2 C14 1.400(7) . ?
C3 C4 1.382(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(6) . ?
C4 H4 0.9300 . ?
C5 C13 1.389(7) . ?
C5 C6 1.487(6) . ?
C6 C12 1.372(6) . ?
C6 C7 1.430(6) . ?
C7 C8 1.357(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.432(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(6) . ?
C9 C11 1.436(6) . ?
C10 C11 1.404(6) 2_766 ?
C10 H10 0.9300 . ?
C11 C10 1.404(6) 2_766 ?
C11 C12 1.425(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.394(8) . ?
C16 C26 1.399(7) . ?
C17 C18 1.379(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.397(7) . ?
C18 H18 0.9300 . ?
C19 C25 1.400(7) . ?
C19 C20 1.486(6) . ?
C20 C21 1.365(6) . ?
C20 C28 1.432(6) . ?
C21 C22 1.432(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.395(6) . ?
C22 C24 1.426(6) . ?
C23 C24 1.388(6) 2_656 ?
C23 H23 0.9300 . ?
C24 C23 1.388(6) 2_656 ?
C24 C27 1.438(6) . ?
C25 C26 1.385(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.350(6) . ?
C27 H27 0.9300 . ?
C28 H28 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
C2 S1 C1 104.1(3) . . ?
C15 S2 C16 105.0(3) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C14 117.4(4) . . ?
C3 C2 S1 116.1(4) . . ?
C14 C2 S1 126.4(4) . . ?
C4 C3 C2 121.3(5) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 121.6(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C13 C5 C4 116.3(4) . . ?
C13 C5 C6 122.8(4) . . ?
C4 C5 C6 120.9(4) . . ?
C12 C6 C7 117.7(4) . . ?
C12 C6 C5 121.9(4) . . ?
C7 C6 C5 120.2(4) . . ?
C8 C7 C6 122.0(4) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 121.4(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 122.6(4) . . ?
C10 C9 C11 120.2(4) . . ?
C8 C9 C11 117.2(4) . . ?
C9 C10 C11 121.5(4) . 2_766 ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 2_766 . ?
C10 C11 C12 122.4(4) 2_766 . ?
C10 C11 C9 118.3(4) 2_766 . ?
C12 C11 C9 119.2(4) . . ?
C6 C12 C11 122.3(4) . . ?
C6 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C14 C13 C5 122.8(4) . . ?
C14 C13 H13 118.6 . . ?
C5 C13 H13 118.6 . . ?
C13 C14 C2 120.6(5) . . ?
C13 C14 H14 119.7 . . ?
C2 C14 H14 119.7 . . ?
S2 C15 H15A 109.5 . . ?
S2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C26 117.7(4) . . ?
C17 C16 S2 116.1(4) . . ?
C26 C16 S2 126.3(4) . . ?
C18 C17 C16 121.5(5) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 121.8(5) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C25 116.1(4) . . ?
C18 C19 C20 120.8(4) . . ?
C25 C19 C20 123.1(4) . . ?
C21 C20 C28 117.9(4) . . ?
C21 C20 C19 121.8(4) . . ?
C28 C20 C19 120.2(4) . . ?
C20 C21 C22 122.3(4) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C23 C22 C24 118.7(4) . . ?
C23 C22 C21 122.3(4) . . ?
C24 C22 C21 119.0(4) . . ?
C24 C23 C22 121.0(4) 2_656 . ?
C24 C23 H23 119.5 2_656 . ?
C22 C23 H23 119.5 . . ?
C23 C24 C22 120.3(4) 2_656 . ?
C23 C24 C27 122.2(4) 2_656 . ?
C22 C24 C27 117.5(4) . . ?
C26 C25 C19 122.7(5) . . ?
C26 C25 H25 118.6 . . ?
C19 C25 H25 118.6 . . ?
C25 C26 C16 120.1(5) . . ?
C25 C26 H26 119.9 . . ?
C16 C26 H26 119.9 . . ?
C28 C27 C24 121.4(4) . . ?
C28 C27 H27 119.3 . . ?
C24 C27 H27 119.3 . . ?
C27 C28 C20 121.9(4) . . ?
C27 C28 H28 119.1 . . ?
C20 C28 H28 119.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1C S2 0.96 2.96 3.740(10) 138.8 1_565
C3 H3 S2 0.93 2.91 3.804(5) 160.9 1_655
C15 H15A S1 0.96 3.00 3.788(9) 140.1 1_445
C17 H17 S1 0.93 2.94 3.825(5) 159.9 .

_refine_diff_density_max         1.178
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.104

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1442078'
_audit_update_record             
;
2015-12-12 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        BOPAnt
_chemical_name_common            ?
_chemical_melting_point          353
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 O2'
_chemical_formula_weight         390.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   7.4376(2)
_cell_length_b                   6.16290(10)
_cell_length_c                   42.296(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1938.71(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7773
_cell_measurement_theta_min      6.70
_cell_measurement_theta_max      69.00

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.648
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10195
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         7.280
_diffrn_reflns_theta_max         69.008
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1777
_reflns_number_gt                1515
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0558P)²+0.2791P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1777
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 1.01001(15) 0.37814(17) 0.71276(2) 0.0544(3) Uani 1 1 d . . . . .
C1 C 0.9135(3) 0.5697(3) 0.72070(4) 0.0713(6) Uani 1 1 d . . . . .
H1A H 0.9532 0.6871 0.7075 0.107 Uiso 1 1 calc R U . . .
H1B H 0.9349 0.6054 0.7425 0.107 Uiso 1 1 calc R U . . .
H1C H 0.7873 0.5459 0.7175 0.107 Uiso 1 1 calc R U . . .
C2 C 0.99915(18) 0.3047(2) 0.68234(3) 0.0403(3) Uani 1 1 d . . . . .
C3 C 0.9020(2) 0.4032(2) 0.65840(3) 0.0440(4) Uani 1 1 d . . . . .
H3 H 0.8364 0.5285 0.6625 0.053 Uiso 1 1 calc R U . . .
C4 C 0.90266(19) 0.3145(2) 0.62835(3) 0.0417(4) Uani 1 1 d . . . . .
H4 H 0.8369 0.3829 0.6125 0.050 Uiso 1 1 calc R U . . .
C5 C 0.99784(16) 0.1270(2) 0.62089(3) 0.0350(3) Uani 1 1 d . . . . .
C6 C 1.00163(16) 0.0365(2) 0.58835(3) 0.0346(3) Uani 1 1 d . . . . .
C7 C 0.95048(17) 0.1562(2) 0.56247(3) 0.0357(3) Uani 1 1 d . . . . .
H7 H 0.9009 0.2930 0.5657 0.043 Uiso 1 1 calc R U . . .
C8 C 0.97029(16) 0.07973(19) 0.53108(3) 0.0333(3) Uani 1 1 d . . . . .
C9 C 0.92689(17) 0.20620(19) 0.50471(3) 0.0356(3) Uani 1 1 d . . . . .
H9 H 0.8777 0.3433 0.5078 0.043 Uiso 1 1 calc R U . . .
C10 C 1.04500(16) -0.13324(19) 0.52593(3) 0.0334(3) Uani 1 1 d . . . . .
C11 C 1.08793(17) -0.2585(2) 0.55322(3) 0.0370(3) Uani 1 1 d . . . . .
H11 H 1.1311 -0.3990 0.5506 0.044 Uiso 1 1 calc R U . . .
C12 C 1.06768(18) -0.1787(2) 0.58269(3) 0.0381(3) Uani 1 1 d . . . . .
H12 H 1.0974 -0.2658 0.5999 0.046 Uiso 1 1 calc R U . . .
C13 C 1.0948(2) 0.1174(2) 0.67564(3) 0.0443(4) Uani 1 1 d . . . . .
H13 H 1.1599 0.0492 0.6916 0.053 Uiso 1 1 calc R U . . .
C14 C 1.09425(19) 0.0315(2) 0.64563(3) 0.0422(3) Uani 1 1 d . . . . .
H14 H 1.1600 -0.0940 0.6417 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3662(16) . ?
O1 C1 1.4217(19) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.3839(19) . ?
C2 C13 1.3855(19) . ?
C3 C4 1.3835(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.3912(18) . ?
C4 H4 0.9300 . ?
C5 C14 1.3984(18) . ?
C5 C6 1.4853(18) . ?
C6 C7 1.3737(18) . ?
C6 C12 1.4344(18) . ?
C7 C8 1.4165(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.3987(17) . ?
C8 C10 1.4418(17) . ?
C9 C10 1.3876(17) 5_756 ?
C9 H9 0.9300 . ?
C10 C9 1.3875(17) 5_756 ?
C10 C11 1.4247(17) . ?
C11 C12 1.3485(18) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.3755(19) . ?
C13 H13 0.9300 . ?
C14 H14 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
C2 O1 C1 117.87(12) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 125.08(12) . . ?
O1 C2 C13 115.97(12) . . ?
C3 C2 C13 118.95(12) . . ?
C4 C3 C2 119.81(13) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 122.55(12) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C14 116.17(12) . . ?
C4 C5 C6 122.11(11) . . ?
C14 C5 C6 121.69(12) . . ?
C7 C6 C12 117.29(12) . . ?
C7 C6 C5 122.10(12) . . ?
C12 C6 C5 120.55(11) . . ?
C6 C7 C8 122.64(12) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C9 C8 C7 122.55(12) . . ?
C9 C8 C10 118.40(11) . . ?
C7 C8 C10 118.99(11) . . ?
C10 C9 C8 121.97(12) 5_756 . ?
C10 C9 H9 119.0 5_756 . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 123.18(11) 5_756 . ?
C9 C10 C8 119.62(11) 5_756 . ?
C11 C10 C8 117.19(11) . . ?
C12 C11 C10 121.77(12) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C6 121.97(12) . . ?
C11 C12 H12 119.0 . . ?
C6 C12 H12 119.0 . . ?
C14 C13 C2 120.51(12) . . ?
C14 C13 H13 119.7 . . ?
C2 C13 H13 119.7 . . ?
C13 C14 C5 122.01(13) . . ?
C13 C14 H14 119.0 . . ?
C5 C14 H14 119.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B O1 0.96 2.57 3.4438(19) 152.3 3_756

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1442079'
_audit_update_record             
;
2015-12-12 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        BEPAnt
_chemical_name_common            ?
_chemical_melting_point          309
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26'
_chemical_formula_weight         386.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.6620(15)
_cell_length_b                   7.71880(10)
_cell_length_c                   6.04260(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.479(7)
_cell_angle_gamma                90
_cell_volume                     1056.00(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9669
_cell_measurement_theta_min      6.90
_cell_measurement_theta_max      68.10

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.514
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13022
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         6.943
_diffrn_reflns_theta_max         68.140
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1910
_reflns_number_gt                1464
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1198P)²+0.0482P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1910
_refine_ls_number_parameters     157
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1890
_refine_ls_wR_factor_gt          0.1786
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.95195(6) 0.04769(16) -0.1435(2) 0.0534(4) Uani 1 1 d . . . . .
C2 C 0.94186(6) -0.02933(17) 0.0689(2) 0.0537(4) Uani 1 1 d . . . . .
C3 C 1.00943(6) 0.07558(17) -0.2052(2) 0.0564(4) Uani 1 1 d . . . . .
H3 H 1.0157 0.1267 -0.3416 0.068 Uiso 1 1 calc R U . . .
C4 C 0.88282(7) -0.05028(18) 0.1341(2) 0.0579(4) Uani 1 1 d . . . . .
H4 H 0.8764 -0.1025 0.2696 0.069 Uiso 1 1 calc R U . . .
C5 C 0.83500(7) 0.00341(17) 0.0054(2) 0.0573(4) Uani 1 1 d . . . . .
C6 C 0.77383(7) -0.00346(18) 0.0853(2) 0.0617(5) Uani 1 1 d . . . . .
C7 C 0.90147(7) 0.09428(18) -0.2783(2) 0.0593(4) Uani 1 1 d . . . . .
H7 H 0.9068 0.1402 -0.4183 0.071 Uiso 1 1 calc R U . . .
C8 C 0.84618(7) 0.07377(18) -0.2090(2) 0.0612(4) Uani 1 1 d . . . . .
H8 H 0.8144 0.1060 -0.3025 0.073 Uiso 1 1 calc R U . . .
C9 C 0.70396(9) -0.0942(2) 0.3536(3) 0.0848(6) Uani 1 1 d . . . . .
H9 H 0.6968 -0.1546 0.4830 0.102 Uiso 1 1 calc R U . . .
C10 C 0.76020(8) -0.0920(2) 0.2769(3) 0.0752(5) Uani 1 1 d . . . . .
H10 H 0.7900 -0.1516 0.3554 0.090 Uiso 1 1 calc R U . . .
C11 C 0.72753(8) 0.0827(3) -0.0237(3) 0.0832(6) Uani 1 1 d . . . . .
H11 H 0.7347 0.1449 -0.1516 0.100 Uiso 1 1 calc R U . . .
C12 C 0.65788(9) -0.0093(3) 0.2437(4) 0.0897(6) Uani 1 1 d D . . . .
C13 C 0.67106(9) 0.0787(3) 0.0530(4) 0.0980(7) Uani 1 1 d . . . . .
H13 H 0.6410 0.1369 -0.0260 0.118 Uiso 1 1 calc R U . . .
C14A C 0.5980(4) -0.0107(14) 0.3304(11) 0.103(3) Uani 0.507(12) 1 d D U P A 1
H14A H 0.5881 -0.1313 0.3549 0.123 Uiso 0.507(12) 1 calc R U P A 1
H14B H 0.6012 0.0434 0.4753 0.123 Uiso 0.507(12) 1 calc R U P A 1
C15A C 0.5514(3) 0.060(2) 0.2249(15) 0.196(6) Uani 0.507(12) 1 d D U P A 1
H15A H 0.5571 0.1828 0.2135 0.294 Uiso 0.507(12) 1 calc R U P A 1
H15B H 0.5166 0.0371 0.3057 0.294 Uiso 0.507(12) 1 calc R U P A 1
H15C H 0.5467 0.0110 0.0792 0.294 Uiso 0.507(12) 1 calc R U P A 1
C14B C 0.5932(6) -0.013(2) 0.356(2) 0.188(6) Uani 0.493(12) 1 d D U P A 2
H14C H 0.5981 -0.0382 0.5132 0.226 Uiso 0.493(12) 1 calc R U P A 2
H14D H 0.5741 0.0991 0.3392 0.226 Uiso 0.493(12) 1 calc R U P A 2
C15B C 0.5598(4) -0.1360(19) 0.254(2) 0.228(7) Uani 0.493(12) 1 d D U P A 2
H15D H 0.5580 -0.1153 0.0976 0.342 Uiso 0.493(12) 1 calc R U P A 2
H15E H 0.5207 -0.1329 0.3091 0.342 Uiso 0.493(12) 1 calc R U P A 2
H15F H 0.5771 -0.2477 0.2840 0.342 Uiso 0.493(12) 1 calc R U P A 2


_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
C1 C3 1.387(2) . ?
C1 C7 1.422(2) . ?
C1 C2 1.441(2) . ?
C2 C3 1.395(2) 3_755 ?
C2 C4 1.420(2) . ?
C3 C2 1.395(2) 3_755 ?
C3 H3 0.9300 . ?
C4 C5 1.370(2) . ?
C4 H4 0.9300 . ?
C5 C8 1.438(2) . ?
C5 C6 1.488(2) . ?
C6 C11 1.385(2) . ?
C6 C10 1.391(2) . ?
C7 C8 1.347(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.375(2) . ?
C9 C12 1.379(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C13 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(3) . ?
C12 C14A 1.476(8) . ?
C12 C14B 1.643(14) . ?
C13 H13 0.9300 . ?
C14A C15A 1.327(11) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C14B C15B 1.347(13) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C7 123.26(12) . . ?
C3 C1 C2 119.36(14) . . ?
C7 C1 C2 117.37(14) . . ?
C3 C2 C4 122.56(13) 3_755 . ?
C3 C2 C1 118.62(14) 3_755 . ?
C4 C2 C1 118.79(14) . . ?
C1 C3 C2 122.01(13) . 3_755 ?
C1 C3 H3 119.0 . . ?
C2 C3 H3 119.0 3_755 . ?
C5 C4 C2 122.66(14) . . ?
C5 C4 H4 118.7 . . ?
C2 C4 H4 118.7 . . ?
C4 C5 C8 117.36(14) . . ?
C4 C5 C6 122.01(14) . . ?
C8 C5 C6 120.58(14) . . ?
C11 C6 C10 116.17(16) . . ?
C11 C6 C5 121.73(14) . . ?
C10 C6 C5 122.07(15) . . ?
C8 C7 C1 121.88(12) . . ?
C8 C7 H7 119.1 . . ?
C1 C7 H7 119.1 . . ?
C7 C8 C5 121.81(13) . . ?
C7 C8 H8 119.1 . . ?
C5 C8 H8 119.1 . . ?
C10 C9 C12 121.70(17) . . ?
C10 C9 H9 119.2 . . ?
C12 C9 H9 119.2 . . ?
C9 C10 C6 121.95(17) . . ?
C9 C10 H10 119.0 . . ?
C6 C10 H10 119.0 . . ?
C13 C11 C6 121.60(17) . . ?
C13 C11 H11 119.2 . . ?
C6 C11 H11 119.2 . . ?
C9 C12 C13 116.68(18) . . ?
C9 C12 C14A 121.0(4) . . ?
C13 C12 C14A 122.4(4) . . ?
C9 C12 C14B 117.6(6) . . ?
C13 C12 C14B 125.6(6) . . ?
C11 C13 C12 121.90(18) . . ?
C11 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15A C14A C12 123.5(5) . . ?
C15A C14A H14A 106.5 . . ?
C12 C14A H14A 106.5 . . ?
C15A C14A H14B 106.5 . . ?
C12 C14A H14B 106.5 . . ?
H14A C14A H14B 106.5 . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C15B C14B C12 108.4(11) . . ?
C15B C14B H14C 110.0 . . ?
C12 C14B H14C 110.0 . . ?
C15B C14B H14D 110.0 . . ?
C12 C14B H14D 110.0 . . ?
H14C C14B H14D 108.4 . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?

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
C3 C1 C2 C3 -0.8(2) . . . 3_755 ?
C7 C1 C2 C3 -179.69(12) . . . 3_755 ?
C3 C1 C2 C4 177.30(11) . . . . ?
C7 C1 C2 C4 -1.61(19) . . . . ?
C7 C1 C3 C2 179.65(12) . . . 3_755 ?
C2 C1 C3 C2 0.8(2) . . . 3_755 ?
C3 C2 C4 C5 176.47(13) 3_755 . . . ?
C1 C2 C4 C5 -1.5(2) . . . . ?
C2 C4 C5 C8 3.8(2) . . . . ?
C2 C4 C5 C6 -173.84(11) . . . . ?
C4 C5 C6 C11 166.32(16) . . . . ?
C8 C5 C6 C11 -11.3(2) . . . . ?
C4 C5 C6 C10 -11.7(2) . . . . ?
C8 C5 C6 C10 170.77(13) . . . . ?
C3 C1 C7 C8 -176.49(12) . . . . ?
C2 C1 C7 C8 2.4(2) . . . . ?
C1 C7 C8 C5 0.0(2) . . . . ?
C4 C5 C8 C7 -3.1(2) . . . . ?
C6 C5 C8 C7 174.62(12) . . . . ?
C12 C9 C10 C6 0.4(3) . . . . ?
C11 C6 C10 C9 0.1(2) . . . . ?
C5 C6 C10 C9 178.19(14) . . . . ?
C10 C6 C11 C13 -0.7(3) . . . . ?
C5 C6 C11 C13 -178.83(16) . . . . ?
C10 C9 C12 C13 -0.2(3) . . . . ?
C10 C9 C12 C14A -179.0(5) . . . . ?
C10 C9 C12 C14B -177.2(6) . . . . ?
C6 C11 C13 C12 0.9(3) . . . . ?
C9 C12 C13 C11 -0.4(3) . . . . ?
C14A C12 C13 C11 178.4(5) . . . . ?
C14B C12 C13 C11 176.3(6) . . . . ?
C9 C12 C14A C15A -175.9(10) . . . . ?
C13 C12 C14A C15A 5.4(14) . . . . ?
C14B C12 C14A C15A 158(16) . . . . ?
C9 C12 C14B C15B -99.4(12) . . . . ?
C13 C12 C14B C15B 84.0(14) . . . . ?
C14A C12 C14B C15B 56(14) . . . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.144

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method Sublimation
