# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_jt308-1
_database_code_depnum_ccdc_archive 'CCDC 1503774'
_audit_update_record             
;
2016-09-10 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14'
_chemical_formula_weight         278.33

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   11.819(5)
_cell_length_b                   10.742(3)
_cell_length_c                   12.543(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.260(5)
_cell_angle_gamma                90.00
_cell_volume                     1463.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    103.1500
_cell_measurement_reflns_used    4009
_cell_measurement_theta_min      3.0436
_cell_measurement_theta_max      27.4083

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.0800
_exptl_crystal_size_mid          0.0400
_exptl_crystal_size_min          0.0200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9233
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
????
;

_diffrn_ambient_temperature      103.1500
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11613
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         27.44
_reflns_number_total             3334
_reflns_number_gt                2933
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    
;
????
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0536P)²+0.8877P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3334
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1340
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.79770(18) 0.16112(16) 1.04282(15) 0.0274(4) Uani 1 1 d . . .
H1 H 0.7124 0.1559 1.0271 0.033 Uiso 1 1 calc R . .
C2 C 0.8822(2) 0.18133(18) 1.15574(16) 0.0352(5) Uani 1 1 d . . .
H2 H 0.8545 0.1892 1.2170 0.042 Uiso 1 1 calc R . .
C3 C 1.0072(2) 0.19006(18) 1.17908(16) 0.0392(5) Uani 1 1 d . . .
H3 H 1.0648 0.2046 1.2561 0.047 Uiso 1 1 calc R . .
C4 C 1.04766(19) 0.17754(19) 1.08984(17) 0.0379(5) Uani 1 1 d . . .
H4 H 1.1331 0.1831 1.1060 0.046 Uiso 1 1 calc R . .
C5 C 0.96393(17) 0.15686(18) 0.97702(16) 0.0312(4) Uani 1 1 d . . .
H5 H 0.9923 0.1484 0.9163 0.037 Uiso 1 1 calc R . .
C6 C 0.83767(16) 0.14845(15) 0.95218(14) 0.0232(4) Uani 1 1 d . . .
C7 C 0.75190(15) 0.12442(15) 0.83508(14) 0.0220(3) Uani 1 1 d . . .
C8 C 0.68437(15) 0.10280(15) 0.73627(14) 0.0205(3) Uani 1 1 d . . .
C9 C 0.60305(14) 0.06945(15) 0.61654(13) 0.0182(3) Uani 1 1 d . . .
C10 C 0.67765(14) 0.03614(14) 0.54422(13) 0.0190(3) Uani 1 1 d . . .
C11 C 0.80273(15) 0.00878(15) 0.59306(14) 0.0215(3) Uani 1 1 d . . .
H6 H 0.8468 0.0140 0.6747 0.026 Uiso 1 1 calc R . .
C12 C 0.86368(16) -0.02622(17) 0.52276(15) 0.0258(4) Uani 1 1 d . . .
H7 H 0.9488 -0.0463 0.5567 0.031 Uiso 1 1 calc R . .
C13 C 0.51543(14) 0.17658(15) 0.55455(13) 0.0190(3) Uani 1 1 d . . .
C14 C 0.49518(16) 0.27932(15) 0.61262(14) 0.0225(4) Uani 1 1 d . . .
H8 H 0.5378 0.2866 0.6943 0.027 Uiso 1 1 calc R . .
C15 C 0.41220(17) 0.37128(16) 0.55039(15) 0.0268(4) Uani 1 1 d . . .
H9 H 0.3986 0.4414 0.5900 0.032 Uiso 1 1 calc R . .
C16 C 0.52341(14) -0.05320(15) 0.62595(13) 0.0184(3) Uani 1 1 d . . .
H14 H 0.5493 -0.0739 0.7100 0.022 Uiso 1 1 calc R . .
C17 C 0.54781(14) -0.16635(15) 0.56580(13) 0.0189(3) Uani 1 1 d . . .
C18 C 0.62990(15) -0.25910(15) 0.62738(14) 0.0224(4) Uani 1 1 d . . .
H10 H 0.6717 -0.2527 0.7092 0.027 Uiso 1 1 calc R . .
C19 C 0.65085(17) -0.36124(16) 0.56928(15) 0.0260(4) Uani 1 1 d . . .
H11 H 0.7079 -0.4238 0.6111 0.031 Uiso 1 1 calc R . .
C20 C 0.38712(14) -0.02823(14) 0.57649(13) 0.0185(3) Uani 1 1 d . . .
C21 C 0.32491(15) 0.00427(15) 0.64649(14) 0.0216(3) Uani 1 1 d . . .
H12 H 0.3682 0.0076 0.7283 0.026 Uiso 1 1 calc R . .
C22 C 0.20018(16) 0.03176(16) 0.59739(15) 0.0258(4) Uani 1 1 d . . .
H13 H 0.1583 0.0543 0.6455 0.031 Uiso 1 1 calc R . .


_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 C2 1.390(2) . ?
C1 C6 1.399(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.441(2) . ?
C7 C8 1.202(2) . ?
C8 C9 1.472(2) . ?
C9 C10 1.536(2) . ?
C9 C13 1.538(2) . ?
C9 C16 1.650(2) . ?
C10 C11 1.390(2) . ?
C10 C20 1.404(2) 3_656 ?
C11 C12 1.393(2) . ?
C11 H6 0.9500 . ?
C12 C22 1.395(2) 3_656 ?
C12 H7 0.9500 . ?
C13 C14 1.394(2) . ?
C13 C17 1.399(2) 3_656 ?
C14 C15 1.394(2) . ?
C14 H8 0.9500 . ?
C15 C19 1.392(2) 3_656 ?
C15 H9 0.9500 . ?
C16 C20 1.504(2) . ?
C16 C17 1.517(2) . ?
C16 H14 1.0000 . ?
C17 C18 1.392(2) . ?
C17 C13 1.399(2) 3_656 ?
C18 C19 1.392(2) . ?
C18 H10 0.9500 . ?
C19 C15 1.392(2) 3_656 ?
C19 H11 0.9500 . ?
C20 C21 1.394(2) . ?
C20 C10 1.404(2) 3_656 ?
C21 C22 1.387(2) . ?
C21 H12 0.9500 . ?
C22 C12 1.395(2) 3_656 ?
C22 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.39(19) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 120.04(19) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.99(17) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.33(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.98(16) . . ?
C1 C6 C7 121.22(16) . . ?
C5 C6 C7 119.79(16) . . ?
C8 C7 C6 177.27(18) . . ?
C7 C8 C9 177.04(17) . . ?
C8 C9 C10 111.30(13) . . ?
C8 C9 C13 111.82(13) . . ?
C10 C9 C13 107.74(12) . . ?
C8 C9 C16 106.40(12) . . ?
C10 C9 C16 109.44(12) . . ?
C13 C9 C16 110.14(12) . . ?
C11 C10 C20 119.65(15) . 3_656 ?
C11 C10 C9 123.20(14) . . ?
C20 C10 C9 117.09(14) 3_656 . ?
C10 C11 C12 120.27(15) . . ?
C10 C11 H6 119.9 . . ?
C12 C11 H6 119.9 . . ?
C11 C12 C22 120.07(16) . 3_656 ?
C11 C12 H7 120.0 . . ?
C22 C12 H7 120.0 3_656 . ?
C14 C13 C17 119.81(15) . 3_656 ?
C14 C13 C9 123.26(14) . . ?
C17 C13 C9 116.92(14) 3_656 . ?
C15 C14 C13 119.77(15) . . ?
C15 C14 H8 120.1 . . ?
C13 C14 H8 120.1 . . ?
C19 C15 C14 120.52(16) 3_656 . ?
C19 C15 H9 119.7 3_656 . ?
C14 C15 H9 119.7 . . ?
C20 C16 C17 108.70(13) . . ?
C20 C16 C9 112.11(13) . . ?
C17 C16 C9 112.22(12) . . ?
C20 C16 H14 107.9 . . ?
C17 C16 H14 107.9 . . ?
C9 C16 H14 107.9 . . ?
C18 C17 C13 120.03(14) . 3_656 ?
C18 C17 C16 121.67(14) . . ?
C13 C17 C16 118.29(14) 3_656 . ?
C17 C18 C19 120.17(15) . . ?
C17 C18 H10 119.9 . . ?
C19 C18 H10 119.9 . . ?
C15 C19 C18 119.70(16) 3_656 . ?
C15 C19 H11 120.2 3_656 . ?
C18 C19 H11 120.2 . . ?
C21 C20 C10 119.73(15) . 3_656 ?
C21 C20 C16 122.02(14) . . ?
C10 C20 C16 118.24(14) 3_656 . ?
C22 C21 C20 120.42(15) . . ?
C22 C21 H12 119.8 . . ?
C20 C21 H12 119.8 . . ?
C21 C22 C12 119.84(16) . 3_656 ?
C21 C22 H13 120.1 . . ?
C12 C22 H13 120.1 3_656 . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_jt309-1-2
_database_code_depnum_ccdc_archive 'CCDC 1503775'
_audit_update_record             
;
2016-09-10 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H28'
_chemical_formula_weight         556.66

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   10.616(4)
_cell_length_b                   18.469(7)
_cell_length_c                   15.306(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.612(7)
_cell_angle_gamma                90.00
_cell_volume                     2950(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    103.1500
_cell_measurement_reflns_used    10364
_cell_measurement_theta_min      3.0328
_cell_measurement_theta_max      27.5204

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.1500
_exptl_crystal_size_min          0.0900
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9192
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
????
;

_diffrn_ambient_temperature      103.1500
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23660
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6719
_reflns_number_gt                6406
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    
;
????
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0572P)²+1.0450P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6719
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.38843(13) 0.40531(7) 0.20453(9) 0.0270(3) Uani 1 1 d . . .
H15 H 0.4467 0.4445 0.2059 0.032 Uiso 1 1 calc R . .
C2 C 0.40952(14) 0.34135(8) 0.16201(9) 0.0317(3) Uani 1 1 d . . .
H16 H 0.4826 0.3368 0.1348 0.038 Uiso 1 1 calc R . .
C3 C 0.32458(15) 0.28419(7) 0.15906(9) 0.0331(3) Uani 1 1 d . . .
H17 H 0.3389 0.2406 0.1293 0.040 Uiso 1 1 calc R . .
C4 C 0.21849(14) 0.29055(7) 0.19955(9) 0.0311(3) Uani 1 1 d . . .
H18 H 0.1604 0.2512 0.1975 0.037 Uiso 1 1 calc R . .
C5 C 0.19666(13) 0.35408(7) 0.24305(8) 0.0253(3) Uani 1 1 d . . .
H19 H 0.1243 0.3579 0.2711 0.030 Uiso 1 1 calc R . .
C6 C 0.28121(12) 0.41231(6) 0.24547(8) 0.0211(2) Uani 1 1 d . . .
C7 C 0.26051(12) 0.47925(6) 0.28896(8) 0.0216(2) Uani 1 1 d . . .
C8 C 0.24911(11) 0.53651(7) 0.32280(8) 0.0207(2) Uani 1 1 d . . .
C9 C 0.24186(11) 0.60886(6) 0.36093(7) 0.0184(2) Uani 1 1 d . . .
C10 C 0.36194(11) 0.62913(6) 0.42957(7) 0.0185(2) Uani 1 1 d . . .
C11 C 0.46968(12) 0.58693(7) 0.45579(8) 0.0218(2) Uani 1 1 d . . .
H24 H 0.4746 0.5397 0.4319 0.026 Uiso 1 1 calc R . .
C12 C 0.57139(12) 0.61471(7) 0.51800(8) 0.0252(3) Uani 1 1 d . . .
H25 H 0.6459 0.5862 0.5367 0.030 Uiso 1 1 calc R . .
C13 C 0.56412(12) 0.68353(7) 0.55256(8) 0.0253(3) Uani 1 1 d . . .
H26 H 0.6333 0.7016 0.5953 0.030 Uiso 1 1 calc R . .
C14 C 0.45590(12) 0.72654(7) 0.52500(8) 0.0215(2) Uani 1 1 d . . .
H27 H 0.4515 0.7740 0.5481 0.026 Uiso 1 1 calc R . .
C15 C 0.35527(11) 0.69902(6) 0.46356(7) 0.0189(2) Uani 1 1 d . . .
C16 C 0.23110(11) 0.73780(6) 0.42464(7) 0.0183(2) Uani 1 1 d . . .
H28 H 0.2267 0.7878 0.4489 0.022 Uiso 1 1 calc R . .
C17 C 0.12251(11) 0.68966(6) 0.44244(7) 0.0186(2) Uani 1 1 d . . .
C18 C 0.02564(12) 0.70912(7) 0.48708(8) 0.0223(3) Uani 1 1 d . . .
H23 H 0.0236 0.7563 0.5115 0.027 Uiso 1 1 calc R . .
C19 C -0.06916(13) 0.65864(7) 0.49593(9) 0.0263(3) Uani 1 1 d . . .
H22 H -0.1362 0.6714 0.5264 0.032 Uiso 1 1 calc R . .
C20 C -0.06534(13) 0.58989(7) 0.46031(9) 0.0265(3) Uani 1 1 d . . .
H21 H -0.1305 0.5559 0.4662 0.032 Uiso 1 1 calc R . .
C21 C 0.03302(12) 0.56983(7) 0.41584(8) 0.0228(3) Uani 1 1 d . . .
H20 H 0.0353 0.5226 0.3916 0.027 Uiso 1 1 calc R . .
C22 C 0.12700(11) 0.61997(6) 0.40770(7) 0.0187(2) Uani 1 1 d . . .
C23 C 0.14698(12) 0.86398(7) 0.30094(8) 0.0233(3) Uani 1 1 d . . .
H1 H 0.0996 0.8567 0.3472 0.028 Uiso 1 1 calc R . .
C24 C 0.14471(14) 0.93118(7) 0.26021(9) 0.0299(3) Uani 1 1 d . . .
H2 H 0.0954 0.9694 0.2782 0.036 Uiso 1 1 calc R . .
C25 C 0.21463(14) 0.94247(7) 0.19314(9) 0.0298(3) Uani 1 1 d . . .
H3 H 0.2148 0.9888 0.1662 0.036 Uiso 1 1 calc R . .
C26 C 0.28421(13) 0.88602(7) 0.16557(9) 0.0267(3) Uani 1 1 d . . .
H4 H 0.3308 0.8935 0.1190 0.032 Uiso 1 1 calc R . .
C27 C 0.28585(12) 0.81870(7) 0.20583(8) 0.0224(2) Uani 1 1 d . . .
H5 H 0.3334 0.7803 0.1864 0.027 Uiso 1 1 calc R . .
C28 C 0.21806(11) 0.80681(6) 0.27482(7) 0.0181(2) Uani 1 1 d . . .
C29 C 0.22513(11) 0.73716(6) 0.32297(7) 0.0172(2) Uani 1 1 d . . .
C30 C 0.22964(11) 0.67059(6) 0.28934(7) 0.0174(2) Uani 1 1 d . . .
C31 C 0.22138(11) 0.64685(6) 0.19583(7) 0.0172(2) Uani 1 1 d . . .
C32 C 0.10090(11) 0.63722(6) 0.14061(8) 0.0185(2) Uani 1 1 d . . .
C33 C -0.01539(12) 0.66106(7) 0.16576(8) 0.0224(3) Uani 1 1 d . . .
H6 H -0.0125 0.6834 0.2220 0.027 Uiso 1 1 calc R . .
C34 C -0.13056(12) 0.65228(7) 0.11018(9) 0.0271(3) Uani 1 1 d . . .
H7 H -0.2064 0.6700 0.1273 0.033 Uiso 1 1 calc R . .
C35 C -0.13817(13) 0.61690(7) 0.02678(9) 0.0277(3) Uani 1 1 d . . .
H8 H -0.2191 0.6104 -0.0109 0.033 Uiso 1 1 calc R . .
C36 C -0.03023(12) 0.59240(7) 0.00073(8) 0.0243(3) Uani 1 1 d . . .
H9 H -0.0367 0.5684 -0.0549 0.029 Uiso 1 1 calc R . .
C37 C 0.09326(12) 0.60210(6) 0.05570(8) 0.0199(2) Uani 1 1 d . . .
C38 C 0.20519(12) 0.57942(6) 0.02879(8) 0.0218(2) Uani 1 1 d . . .
H10 H 0.1996 0.5554 -0.0267 0.026 Uiso 1 1 calc R . .
C39 C 0.32545(12) 0.59121(6) 0.08153(8) 0.0201(2) Uani 1 1 d . . .
C40 C 0.44101(13) 0.56998(7) 0.05328(9) 0.0256(3) Uani 1 1 d . . .
H11 H 0.4368 0.5495 -0.0041 0.031 Uiso 1 1 calc R . .
C41 C 0.55706(13) 0.57869(7) 0.10725(10) 0.0291(3) Uani 1 1 d . . .
H12 H 0.6326 0.5630 0.0879 0.035 Uiso 1 1 calc R . .
C42 C 0.56608(12) 0.61109(7) 0.19236(9) 0.0270(3) Uani 1 1 d . . .
H13 H 0.6475 0.6168 0.2297 0.032 Uiso 1 1 calc R . .
C43 C 0.45811(12) 0.63407(7) 0.22078(8) 0.0223(2) Uani 1 1 d . . .
H14 H 0.4656 0.6566 0.2773 0.027 Uiso 1 1 calc R . .
C44 C 0.33420(11) 0.62486(6) 0.16694(7) 0.0184(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3867(19) . ?
C1 C6 1.4027(19) . ?
C1 H15 0.9500 . ?
C2 C3 1.384(2) . ?
C2 H16 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H17 0.9500 . ?
C4 C5 1.3894(19) . ?
C4 H18 0.9500 . ?
C5 C6 1.3969(18) . ?
C5 H19 0.9500 . ?
C6 C7 1.4400(17) . ?
C7 C8 1.1935(18) . ?
C8 C9 1.4658(17) . ?
C9 C22 1.5371(17) . ?
C9 C10 1.5414(16) . ?
C9 C30 1.5702(16) . ?
C10 C11 1.3813(17) . ?
C10 C15 1.3983(17) . ?
C11 C12 1.3990(18) . ?
C11 H24 0.9500 . ?
C12 C13 1.3844(19) . ?
C12 H25 0.9500 . ?
C13 C14 1.3965(18) . ?
C13 H26 0.9500 . ?
C14 C15 1.3835(17) . ?
C14 H27 0.9500 . ?
C15 C16 1.5219(17) . ?
C16 C17 1.5197(16) . ?
C16 C29 1.5456(16) . ?
C16 H28 1.0000 . ?
C17 C18 1.3829(17) . ?
C17 C22 1.3969(17) . ?
C18 C19 1.3967(18) . ?
C18 H23 0.9500 . ?
C19 C20 1.3853(19) . ?
C19 H22 0.9500 . ?
C20 C21 1.3974(18) . ?
C20 H21 0.9500 . ?
C21 C22 1.3836(17) . ?
C21 H20 0.9500 . ?
C23 C24 1.3872(18) . ?
C23 C28 1.3982(17) . ?
C23 H1 0.9500 . ?
C24 C25 1.389(2) . ?
C24 H2 0.9500 . ?
C25 C26 1.388(2) . ?
C25 H3 0.9500 . ?
C26 C27 1.3864(18) . ?
C26 H4 0.9500 . ?
C27 C28 1.4004(17) . ?
C27 H5 0.9500 . ?
C28 C29 1.4777(16) . ?
C29 C30 1.3371(17) . ?
C30 C31 1.4839(16) . ?
C31 C32 1.4085(17) . ?
C31 C44 1.4107(17) . ?
C32 C33 1.4287(17) . ?
C32 C37 1.4414(17) . ?
C33 C34 1.3646(18) . ?
C33 H6 0.9500 . ?
C34 C35 1.423(2) . ?
C34 H7 0.9500 . ?
C35 C36 1.358(2) . ?
C35 H8 0.9500 . ?
C36 C37 1.4326(17) . ?
C36 H9 0.9500 . ?
C37 C38 1.3918(18) . ?
C38 C39 1.3962(18) . ?
C38 H10 0.9500 . ?
C39 C40 1.4287(18) . ?
C39 C44 1.4349(17) . ?
C40 C41 1.361(2) . ?
C40 H11 0.9500 . ?
C41 C42 1.421(2) . ?
C41 H12 0.9500 . ?
C42 C43 1.3662(18) . ?
C42 H13 0.9500 . ?
C43 C44 1.4280(17) . ?
C43 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.17(13) . . ?
C2 C1 H15 119.9 . . ?
C6 C1 H15 119.9 . . ?
C3 C2 C1 120.30(13) . . ?
C3 C2 H16 119.8 . . ?
C1 C2 H16 119.8 . . ?
C2 C3 C4 119.92(13) . . ?
C2 C3 H17 120.0 . . ?
C4 C3 H17 120.0 . . ?
C3 C4 C5 120.43(13) . . ?
C3 C4 H18 119.8 . . ?
C5 C4 H18 119.8 . . ?
C4 C5 C6 119.98(13) . . ?
C4 C5 H19 120.0 . . ?
C6 C5 H19 120.0 . . ?
C5 C6 C1 119.18(12) . . ?
C5 C6 C7 121.41(12) . . ?
C1 C6 C7 119.41(11) . . ?
C8 C7 C6 176.07(13) . . ?
C7 C8 C9 175.96(13) . . ?
C8 C9 C22 114.29(10) . . ?
C8 C9 C10 113.29(10) . . ?
C22 C9 C10 106.12(9) . . ?
C8 C9 C30 112.82(10) . . ?
C22 C9 C30 104.91(9) . . ?
C10 C9 C30 104.53(9) . . ?
C11 C10 C15 120.58(11) . . ?
C11 C10 C9 126.70(11) . . ?
C15 C10 C9 112.68(10) . . ?
C10 C11 C12 119.00(12) . . ?
C10 C11 H24 120.5 . . ?
C12 C11 H24 120.5 . . ?
C13 C12 C11 120.43(12) . . ?
C13 C12 H25 119.8 . . ?
C11 C12 H25 119.8 . . ?
C12 C13 C14 120.49(12) . . ?
C12 C13 H26 119.8 . . ?
C14 C13 H26 119.8 . . ?
C15 C14 C13 119.06(12) . . ?
C15 C14 H27 120.5 . . ?
C13 C14 H27 120.5 . . ?
C14 C15 C10 120.42(11) . . ?
C14 C15 C16 126.72(11) . . ?
C10 C15 C16 112.85(10) . . ?
C17 C16 C15 106.59(10) . . ?
C17 C16 C29 106.51(9) . . ?
C15 C16 C29 105.21(9) . . ?
C17 C16 H28 112.7 . . ?
C15 C16 H28 112.7 . . ?
C29 C16 H28 112.7 . . ?
C18 C17 C22 120.54(11) . . ?
C18 C17 C16 126.46(11) . . ?
C22 C17 C16 112.99(10) . . ?
C17 C18 C19 119.28(12) . . ?
C17 C18 H23 120.4 . . ?
C19 C18 H23 120.4 . . ?
C20 C19 C18 119.99(12) . . ?
C20 C19 H22 120.0 . . ?
C18 C19 H22 120.0 . . ?
C19 C20 C21 120.89(12) . . ?
C19 C20 H21 119.6 . . ?
C21 C20 H21 119.6 . . ?
C22 C21 C20 118.84(12) . . ?
C22 C21 H20 120.6 . . ?
C20 C21 H20 120.6 . . ?
C21 C22 C17 120.44(11) . . ?
C21 C22 C9 126.85(11) . . ?
C17 C22 C9 112.70(10) . . ?
C24 C23 C28 120.85(12) . . ?
C24 C23 H1 119.6 . . ?
C28 C23 H1 119.6 . . ?
C23 C24 C25 119.94(12) . . ?
C23 C24 H2 120.0 . . ?
C25 C24 H2 120.0 . . ?
C26 C25 C24 119.93(12) . . ?
C26 C25 H3 120.0 . . ?
C24 C25 H3 120.0 . . ?
C27 C26 C25 120.16(12) . . ?
C27 C26 H4 119.9 . . ?
C25 C26 H4 119.9 . . ?
C26 C27 C28 120.64(12) . . ?
C26 C27 H5 119.7 . . ?
C28 C27 H5 119.7 . . ?
C23 C28 C27 118.45(11) . . ?
C23 C28 C29 119.69(11) . . ?
C27 C28 C29 121.78(11) . . ?
C30 C29 C28 127.63(11) . . ?
C30 C29 C16 113.39(10) . . ?
C28 C29 C16 118.97(10) . . ?
C29 C30 C31 130.02(10) . . ?
C29 C30 C9 113.78(10) . . ?
C31 C30 C9 116.18(10) . . ?
C32 C31 C44 120.34(11) . . ?
C32 C31 C30 120.12(10) . . ?
C44 C31 C30 118.99(10) . . ?
C31 C32 C33 122.25(11) . . ?
C31 C32 C37 119.47(11) . . ?
C33 C32 C37 118.28(11) . . ?
C34 C33 C32 120.99(12) . . ?
C34 C33 H6 119.5 . . ?
C32 C33 H6 119.5 . . ?
C33 C34 C35 120.68(12) . . ?
C33 C34 H7 119.7 . . ?
C35 C34 H7 119.7 . . ?
C36 C35 C34 120.31(12) . . ?
C36 C35 H8 119.8 . . ?
C34 C35 H8 119.8 . . ?
C35 C36 C37 121.07(12) . . ?
C35 C36 H9 119.5 . . ?
C37 C36 H9 119.5 . . ?
C38 C37 C36 121.83(11) . . ?
C38 C37 C32 119.53(11) . . ?
C36 C37 C32 118.63(11) . . ?
C37 C38 C39 121.44(11) . . ?
C37 C38 H10 119.3 . . ?
C39 C38 H10 119.3 . . ?
C38 C39 C40 121.80(11) . . ?
C38 C39 C44 119.54(11) . . ?
C40 C39 C44 118.65(11) . . ?
C41 C40 C39 121.05(12) . . ?
C41 C40 H11 119.5 . . ?
C39 C40 H11 119.5 . . ?
C40 C41 C42 120.47(12) . . ?
C40 C41 H12 119.8 . . ?
C42 C41 H12 119.8 . . ?
C43 C42 C41 120.26(12) . . ?
C43 C42 H13 119.9 . . ?
C41 C42 H13 119.9 . . ?
C42 C43 C44 121.13(12) . . ?
C42 C43 H14 119.4 . . ?
C44 C43 H14 119.4 . . ?
C31 C44 C43 122.00(11) . . ?
C31 C44 C39 119.60(11) . . ?
C43 C44 C39 118.39(11) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_chemical_absolute_configuration ?
