# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_g:\140519c\work\mo_140519c_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20'
_chemical_formula_weight         332.42

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   P2(1)

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

_cell_length_a                   9.8251(19)
_cell_length_b                   9.5020(18)
_cell_length_c                   10.709(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.096(3)
_cell_angle_gamma                90.00
_cell_volume                     955.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4239
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      31.23

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9871
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9662
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5085
_reflns_number_gt                4252
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0709P)²+0.0441P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -5(10)
_refine_ls_number_reflns         5085
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.38719(13) 0.80074(15) 0.80018(12) 0.0413(3) Uani 1 1 d . . .
C2 C 0.24937(13) 0.76596(15) 0.74094(12) 0.0415(3) Uani 1 1 d . . .
C3 C 0.45162(16) 0.80730(18) 0.94461(13) 0.0505(3) Uani 1 1 d . . .
C4 C 0.58528(19) 0.7488(2) 1.00073(16) 0.0685(5) Uani 1 1 d . . .
H4 H 0.6324 0.7046 0.9479 0.082 Uiso 1 1 calc R . .
C5 C 0.6493(3) 0.7554(4) 1.1344(2) 0.1094(11) Uani 1 1 d . . .
H5 H 0.7384 0.7149 1.1706 0.131 Uiso 1 1 calc R . .
C6 C 0.5831(5) 0.8202(5) 1.2122(2) 0.1366(17) Uani 1 1 d . . .
H6 H 0.6268 0.8248 1.3018 0.164 Uiso 1 1 calc R . .
C7 C 0.4515(5) 0.8795(4) 1.1594(3) 0.1238(14) Uani 1 1 d . . .
H7 H 0.4065 0.9236 1.2140 0.149 Uiso 1 1 calc R . .
C8 C 0.3833(3) 0.8749(3) 1.0240(2) 0.0805(6) Uani 1 1 d . . .
H8 H 0.2945 0.9162 0.9887 0.097 Uiso 1 1 calc R . .
C9 C 0.48793(13) 0.83288(16) 0.72353(12) 0.0418(3) Uani 1 1 d . . .
C10 C 0.56368(16) 0.95829(19) 0.74251(15) 0.0523(3) Uani 1 1 d . . .
H10 H 0.5531 1.0222 0.8048 0.063 Uiso 1 1 calc R . .
C11 C 0.65531(18) 0.9887(2) 0.66883(17) 0.0636(5) Uani 1 1 d . . .
H11 H 0.7032 1.0744 0.6799 0.076 Uiso 1 1 calc R . .
C12 C 0.67546(18) 0.8937(3) 0.58030(17) 0.0671(5) Uani 1 1 d . . .
H12 H 0.7377 0.9143 0.5320 0.081 Uiso 1 1 calc R . .
C13 C 0.60354(18) 0.7668(2) 0.56234(16) 0.0626(4) Uani 1 1 d . . .
H13 H 0.6180 0.7018 0.5026 0.075 Uiso 1 1 calc R . .
C14 C 0.50953(15) 0.73622(18) 0.63359(13) 0.0491(3) Uani 1 1 d . . .
H14 H 0.4610 0.6509 0.6211 0.059 Uiso 1 1 calc R . .
C15 C 0.18336(13) 0.77951(16) 0.59715(13) 0.0444(3) Uani 1 1 d . . .
C16 C 0.20167(17) 0.8993(2) 0.52871(17) 0.0597(4) Uani 1 1 d . . .
H16 H 0.2554 0.9740 0.5735 0.072 Uiso 1 1 calc R . .
C17 C 0.1408(2) 0.9084(3) 0.39475(19) 0.0727(5) Uani 1 1 d . . .
H17 H 0.1548 0.9887 0.3504 0.087 Uiso 1 1 calc R . .
C18 C 0.0599(2) 0.7996(3) 0.32689(18) 0.0758(6) Uani 1 1 d . . .
H18 H 0.0204 0.8057 0.2368 0.091 Uiso 1 1 calc R . .
C19 C 0.0375(2) 0.6819(3) 0.39255(18) 0.0715(5) Uani 1 1 d . . .
H19 H -0.0186 0.6089 0.3470 0.086 Uiso 1 1 calc R . .
C20 C 0.09868(16) 0.67156(19) 0.52708(16) 0.0547(4) Uani 1 1 d . . .
H20 H 0.0828 0.5915 0.5708 0.066 Uiso 1 1 calc R . .
C21 C 0.15475(14) 0.70927(16) 0.81536(13) 0.0431(3) Uani 1 1 d . . .
C22 C 0.01702(15) 0.76170(19) 0.79318(16) 0.0520(3) Uani 1 1 d . . .
H22 H -0.0152 0.8331 0.7323 0.062 Uiso 1 1 calc R . .
C23 C -0.07237(17) 0.7089(2) 0.86065(17) 0.0611(4) Uani 1 1 d . . .
H23 H -0.1637 0.7451 0.8455 0.073 Uiso 1 1 calc R . .
C24 C -0.0257(2) 0.6032(3) 0.94954(18) 0.0710(5) Uani 1 1 d . . .
H24 H -0.0850 0.5687 0.9961 0.085 Uiso 1 1 calc R . .
C25 C 0.1089(2) 0.5475(2) 0.97053(19) 0.0703(5) Uani 1 1 d . . .
H25 H 0.1394 0.4745 1.0300 0.084 Uiso 1 1 calc R . .
C26 C 0.19878(18) 0.59989(18) 0.90338(16) 0.0556(4) Uani 1 1 d . . .
H26 H 0.2891 0.5614 0.9175 0.067 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 1.3566(18) . ?
C1 C3 1.4903(19) . ?
C1 C9 1.4914(17) . ?
C2 C15 1.4904(18) . ?
C2 C21 1.4916(18) . ?
C3 C8 1.386(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.347(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.408(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.388(2) . ?
C9 C14 1.392(2) . ?
C10 C11 1.391(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.393(2) . ?
C15 C16 1.394(2) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.392(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.384(2) . ?
C21 C22 1.395(2) . ?
C22 C23 1.385(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.366(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.380(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(2) . ?
C25 H25 0.9300 . ?
C26 H26 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 C1 C3 123.81(11) . . ?
C2 C1 C9 121.68(11) . . ?
C3 C1 C9 114.49(11) . . ?
C1 C2 C15 122.24(11) . . ?
C1 C2 C21 122.10(11) . . ?
C15 C2 C21 115.66(11) . . ?
C8 C3 C4 119.11(17) . . ?
C8 C3 C1 121.44(17) . . ?
C4 C3 C1 119.42(14) . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C8 121.1(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 118.5(3) . . ?
C3 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C10 C9 C14 118.93(13) . . ?
C10 C9 C1 120.61(13) . . ?
C14 C9 C1 120.45(13) . . ?
C9 C10 C11 120.27(16) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.44(17) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.08(14) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.04(17) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.20(16) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C20 C15 C16 117.84(14) . . ?
C20 C15 C2 120.17(13) . . ?
C16 C15 C2 121.99(14) . . ?
C17 C16 C15 120.83(19) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.47(19) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 119.78(16) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.88(17) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C26 C21 C22 118.51(13) . . ?
C26 C21 C2 121.06(13) . . ?
C22 C21 C2 120.38(13) . . ?
C23 C22 C21 120.91(16) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C24 C23 C22 119.71(16) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.27(15) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 120.30(18) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 120.26(16) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 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
C3 C1 C2 C15 171.39(14) . . . . ?
C9 C1 C2 C15 -10.0(2) . . . . ?
C3 C1 C2 C21 -9.7(2) . . . . ?
C9 C1 C2 C21 168.96(14) . . . . ?
C2 C1 C3 C8 -46.6(2) . . . . ?
C9 C1 C3 C8 134.68(17) . . . . ?
C2 C1 C3 C4 135.69(16) . . . . ?
C9 C1 C3 C4 -43.1(2) . . . . ?
C8 C3 C4 C5 1.0(3) . . . . ?
C1 C3 C4 C5 178.78(18) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 -0.4(5) . . . . ?
C4 C3 C8 C7 -1.0(3) . . . . ?
C1 C3 C8 C7 -178.75(19) . . . . ?
C6 C7 C8 C3 0.7(4) . . . . ?
C2 C1 C9 C10 125.83(15) . . . . ?
C3 C1 C9 C10 -55.40(18) . . . . ?
C2 C1 C9 C14 -55.43(19) . . . . ?
C3 C1 C9 C14 123.34(15) . . . . ?
C14 C9 C10 C11 2.5(2) . . . . ?
C1 C9 C10 C11 -178.73(14) . . . . ?
C9 C10 C11 C12 -2.2(3) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C9 -0.3(2) . . . . ?
C10 C9 C14 C13 -1.3(2) . . . . ?
C1 C9 C14 C13 179.96(14) . . . . ?
C1 C2 C15 C20 135.24(15) . . . . ?
C21 C2 C15 C20 -43.74(18) . . . . ?
C1 C2 C15 C16 -45.7(2) . . . . ?
C21 C2 C15 C16 135.31(14) . . . . ?
C20 C15 C16 C17 -1.8(2) . . . . ?
C2 C15 C16 C17 179.08(15) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
C18 C19 C20 C15 -0.1(3) . . . . ?
C16 C15 C20 C19 1.6(2) . . . . ?
C2 C15 C20 C19 -179.30(14) . . . . ?
C1 C2 C21 C26 -48.7(2) . . . . ?
C15 C2 C21 C26 130.25(15) . . . . ?
C1 C2 C21 C22 134.12(16) . . . . ?
C15 C2 C21 C22 -46.90(19) . . . . ?
C26 C21 C22 C23 2.1(2) . . . . ?
C2 C21 C22 C23 179.29(14) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
C22 C23 C24 C25 -1.1(3) . . . . ?
C23 C24 C25 C26 1.1(3) . . . . ?
C22 C21 C26 C25 -2.1(2) . . . . ?
C2 C21 C26 C25 -179.27(16) . . . . ?
C24 C25 C26 C21 0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 1006150'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_e:\140321d\work\t

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24'
_chemical_formula_weight         360.47

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.036(19)
_cell_length_b                   9.48(2)
_cell_length_c                   12.90(3)
_cell_angle_alpha                111.14(3)
_cell_angle_beta                 98.54(5)
_cell_angle_gamma                98.34(3)
_cell_volume                     995(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2704
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      28.50

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9919
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6931
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3455
_reflns_number_gt                2652
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0779P)²+0.3109P] 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         3455
_refine_ls_number_parameters     296
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1694
_refine_ls_wR_factor_gt          0.1537
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.044
_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 -0.1038(2) 0.6044(2) 0.26374(17) 0.0485(5) Uani 1 1 d . . .
C2 C -0.2419(2) 0.6192(2) 0.29145(18) 0.0538(5) Uani 1 1 d . . .
H2 H -0.2681 0.7155 0.3136 0.065 Uiso 1 1 calc R . .
C3 C -0.3415(3) 0.4945(3) 0.2870(2) 0.0705(7) Uani 1 1 d . . .
H3 H -0.4359 0.5053 0.3057 0.085 Uiso 1 1 calc R . .
C4 C -0.3037(4) 0.3546(3) 0.2554(2) 0.0821(8) Uani 1 1 d . . .
H4 H -0.3729 0.2691 0.2515 0.099 Uiso 1 1 calc R . .
C5 C -0.1661(4) 0.3379(3) 0.2294(2) 0.0825(8) Uani 1 1 d . . .
H5 H -0.1403 0.2415 0.2080 0.099 Uiso 1 1 calc R . .
C6 C -0.0665(3) 0.4617(3) 0.2345(2) 0.0694(7) Uani 1 1 d . . .
H6 H 0.0289 0.4505 0.2181 0.083 Uiso 1 1 calc R . .
C7 C 0.1616(2) 0.7565(2) 0.33173(17) 0.0498(5) Uani 1 1 d . . .
C8 C 0.2884(2) 0.7896(3) 0.2925(2) 0.0607(6) Uani 1 1 d . . .
H8 H 0.2769 0.8003 0.2231 0.073 Uiso 1 1 calc R . .
C9 C 0.4306(3) 0.8074(4) 0.3524(3) 0.0852(9) Uani 1 1 d . . .
H9 H 0.5153 0.8314 0.3241 0.102 Uiso 1 1 calc R . .
C10 C 0.4509(3) 0.7908(4) 0.4517(3) 0.0950(10) Uani 1 1 d . . .
H10 H 0.5491 0.8049 0.4933 0.114 Uiso 1 1 calc R . .
C11 C 0.3273(4) 0.7535(4) 0.4906(3) 0.0958(10) Uani 1 1 d . . .
H11 H 0.3403 0.7396 0.5589 0.115 Uiso 1 1 calc R . .
C12 C 0.1840(3) 0.7359(3) 0.4316(2) 0.0741(7) Uani 1 1 d . . .
H12 H 0.0998 0.7094 0.4597 0.089 Uiso 1 1 calc R . .
C13 C 0.0061(2) 0.7370(2) 0.26894(16) 0.0440(5) Uani 1 1 d . A .
C14 C -0.0337(2) 0.8335(2) 0.22223(16) 0.0434(5) Uani 1 1 d D . .
C15 C -0.1888(2) 0.8124(2) 0.15517(17) 0.0458(5) Uani 1 1 d . A .
C16 C -0.2562(2) 0.6873(2) 0.05628(18) 0.0543(5) Uani 1 1 d . . .
C17 C -0.4028(3) 0.6814(3) 0.0017(2) 0.0663(6) Uani 1 1 d . A .
H17 H -0.4502 0.5970 -0.0655 0.080 Uiso 1 1 calc R . .
C18 C -0.4784(3) 0.7950(3) 0.0436(3) 0.0756(7) Uani 1 1 d . . .
H18 H -0.5769 0.7875 0.0056 0.091 Uiso 1 1 calc R A .
C19 C -0.4128(3) 0.9177(3) 0.1391(3) 0.0727(7) Uani 1 1 d . A .
H19 H -0.4652 0.9958 0.1678 0.087 Uiso 1 1 calc R . .
C20 C -0.2689(2) 0.9280(3) 0.1943(2) 0.0571(6) Uani 1 1 d . . .
H20 H -0.2229 1.0151 0.2602 0.069 Uiso 1 1 calc R A .
C21 C -0.1803(3) 0.5625(3) 0.0052(2) 0.0744(7) Uani 1 1 d . A .
H21A H -0.0713 0.5993 0.0307 0.112 Uiso 1 1 calc R . .
H21B H -0.2075 0.5273 -0.0763 0.112 Uiso 1 1 calc R . .
H21C H -0.2120 0.4783 0.0273 0.112 Uiso 1 1 calc R . .
C22 C 0.0696(3) 0.9854(2) 0.2512(2) 0.0407(9) Uani 0.702(5) 1 d PGD A 1
C23 C 0.1330(3) 1.0182(3) 0.16853(19) 0.0467(9) Uani 0.702(5) 1 d PG A 1
C24 C 0.2207(3) 1.1647(3) 0.1948(2) 0.0629(13) Uani 0.702(5) 1 d PG A 1
H24 H 0.2631 1.1867 0.1395 0.075 Uiso 0.702(5) 1 calc PR A 1
C25 C 0.2450(3) 1.2783(2) 0.3038(3) 0.0738(14) Uani 0.702(5) 1 d PG A 1
H25 H 0.3037 1.3763 0.3214 0.089 Uiso 0.702(5) 1 calc PR A 1
C26 C 0.1817(3) 1.2454(2) 0.3865(2) 0.0656(10) Uani 0.702(5) 1 d PG A 1
H26 H 0.1980 1.3214 0.4594 0.079 Uiso 0.702(5) 1 calc PR A 1
C27 C 0.0940(3) 1.0990(3) 0.36022(19) 0.0496(9) Uani 0.702(5) 1 d PG A 1
H27 H 0.0516 1.0770 0.4156 0.060 Uiso 0.702(5) 1 calc PR A 1
C28 C 0.1144(5) 0.9004(5) 0.0550(3) 0.0657(11) Uani 0.702(5) 1 d P A 1
H28A H 0.1687 0.9433 0.0109 0.099 Uiso 0.702(5) 1 calc PR A 1
H28B H 0.0075 0.8659 0.0187 0.099 Uiso 0.702(5) 1 calc PR A 1
H28C H 0.1546 0.8144 0.0603 0.099 Uiso 0.702(5) 1 calc PR A 1
C22' C 0.0661(8) 0.9566(7) 0.2161(6) 0.055(3) Uani 0.298(5) 1 d PGDU A 2
C23' C 0.1278(8) 1.0879(8) 0.3151(5) 0.054(2) Uani 0.298(5) 1 d PGU A 2
C24' C 0.2281(8) 1.2116(7) 0.3121(6) 0.072(3) Uani 0.298(5) 1 d PGU A 2
H24' H 0.2694 1.2995 0.3784 0.086 Uiso 0.298(5) 1 calc PR A 2
C25' C 0.2667(8) 1.2040(8) 0.2101(7) 0.092(5) Uani 0.298(5) 1 d PGU A 2
H25' H 0.3338 1.2867 0.2082 0.110 Uiso 0.298(5) 1 calc PR A 2
C26' C 0.2050(8) 1.0726(9) 0.1111(6) 0.080(3) Uani 0.298(5) 1 d PGU A 2
H26' H 0.2308 1.0675 0.0429 0.097 Uiso 0.298(5) 1 calc PR A 2
C27' C 0.1047(8) 0.9490(8) 0.1141(5) 0.059(3) Uani 0.298(5) 1 d PGU A 2
H27' H 0.0634 0.8611 0.0479 0.071 Uiso 0.298(5) 1 calc PR A 2
C28' C 0.0963(13) 1.0946(12) 0.4274(8) 0.084(3) Uani 0.298(5) 1 d P A 2
H28D H -0.0070 1.0407 0.4164 0.127 Uiso 0.298(5) 1 calc PR A 2
H28E H 0.1094 1.2007 0.4781 0.127 Uiso 0.298(5) 1 calc PR A 2
H28F H 0.1662 1.0466 0.4597 0.127 Uiso 0.298(5) 1 calc PR 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 C2 1.361(4) . ?
C1 C6 1.374(4) . ?
C1 C13 1.459(3) . ?
C2 C3 1.356(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.351(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.352(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.345(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.360(4) . ?
C7 C12 1.362(5) . ?
C7 C13 1.464(4) . ?
C8 C9 1.350(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.335(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.343(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.355(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.326(3) . ?
C14 C22' 1.401(5) . ?
C14 C15 1.478(4) . ?
C14 C22 1.484(3) . ?
C15 C16 1.368(4) . ?
C15 C20 1.386(4) . ?
C16 C17 1.389(4) . ?
C16 C21 1.453(4) . ?
C17 C18 1.350(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.331(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.3900 . ?
C22 C27 1.3900 . ?
C23 C24 1.3900 . ?
C23 C28 1.454(5) . ?
C24 C25 1.3900 . ?
C24 H24 0.9300 . ?
C25 C26 1.3900 . ?
C25 H25 0.9300 . ?
C26 C27 1.3900 . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C22' C23' 1.3900 . ?
C22' C27' 1.3900 . ?
C23' C24' 1.3900 . ?
C23' C28' 1.499(12) . ?
C24' C25' 1.3900 . ?
C24' H24' 0.9300 . ?
C25' C26' 1.3900 . ?
C25' H25' 0.9300 . ?
C26' C27' 1.3900 . ?
C26' H26' 0.9300 . ?
C27' H27' 0.9300 . ?
C28' H28D 0.9600 . ?
C28' H28E 0.9600 . ?
C28' H28F 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
C2 C1 C6 118.5(2) . . ?
C2 C1 C13 121.5(2) . . ?
C6 C1 C13 120.0(2) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C12 117.1(2) . . ?
C8 C7 C13 122.6(2) . . ?
C12 C7 C13 120.2(2) . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 118.9(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 C1 122.1(2) . . ?
C14 C13 C7 123.08(18) . . ?
C1 C13 C7 114.75(19) . . ?
C13 C14 C22' 125.8(4) . . ?
C13 C14 C15 123.71(18) . . ?
C22' C14 C15 110.0(4) . . ?
C13 C14 C22 120.5(2) . . ?
C22' C14 C22 16.8(3) . . ?
C15 C14 C22 115.0(2) . . ?
C16 C15 C20 118.4(2) . . ?
C16 C15 C14 123.9(2) . . ?
C20 C15 C14 117.6(2) . . ?
C15 C16 C17 118.2(2) . . ?
C15 C16 C21 123.1(2) . . ?
C17 C16 C21 118.8(2) . . ?
C18 C17 C16 121.7(3) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.6(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C15 121.7(3) . . ?
C19 C20 H20 119.1 . . ?
C15 C20 H20 119.1 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 120.0 . . ?
C23 C22 C14 120.61(19) . . ?
C27 C22 C14 119.24(19) . . ?
C24 C23 C22 120.0 . . ?
C24 C23 C28 118.6(2) . . ?
C22 C23 C28 121.4(3) . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C22 120.0 . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
C23' C22' C27' 120.0 . . ?
C23' C22' C14 118.5(5) . . ?
C27' C22' C14 121.5(4) . . ?
C24' C23' C22' 120.0 . . ?
C24' C23' C28' 118.9(6) . . ?
C22' C23' C28' 120.9(6) . . ?
C23' C24' C25' 120.0 . . ?
C23' C24' H24' 120.0 . . ?
C25' C24' H24' 120.0 . . ?
C24' C25' C26' 120.0 . . ?
C24' C25' H25' 120.0 . . ?
C26' C25' H25' 120.0 . . ?
C27' C26' C25' 120.0 . . ?
C27' C26' H26' 120.0 . . ?
C25' C26' H26' 120.0 . . ?
C26' C27' C22' 120.0 . . ?
C26' C27' H27' 120.0 . . ?
C22' C27' H27' 120.0 . . ?
C23' C28' H28D 109.5 . . ?
C23' C28' H28E 109.5 . . ?
H28D C28' H28E 109.5 . . ?
C23' C28' H28F 109.5 . . ?
H28D C28' H28F 109.5 . . ?
H28E C28' H28F 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
C6 C1 C2 C3 -1.8(3) . . . . ?
C13 C1 C2 C3 -179.3(2) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C2 C1 C6 C5 2.3(3) . . . . ?
C13 C1 C6 C5 179.9(2) . . . . ?
C12 C7 C8 C9 -2.5(4) . . . . ?
C13 C7 C8 C9 179.8(2) . . . . ?
C7 C8 C9 C10 0.9(5) . . . . ?
C8 C9 C10 C11 1.1(5) . . . . ?
C9 C10 C11 C12 -1.4(6) . . . . ?
C10 C11 C12 C7 -0.4(5) . . . . ?
C8 C7 C12 C11 2.3(4) . . . . ?
C13 C7 C12 C11 180.0(3) . . . . ?
C2 C1 C13 C14 -48.8(3) . . . . ?
C6 C1 C13 C14 133.7(3) . . . . ?
C2 C1 C13 C7 129.8(2) . . . . ?
C6 C1 C13 C7 -47.7(3) . . . . ?
C8 C7 C13 C14 -45.9(3) . . . . ?
C12 C7 C13 C14 136.5(2) . . . . ?
C8 C7 C13 C1 135.5(2) . . . . ?
C12 C7 C13 C1 -42.1(3) . . . . ?
C1 C13 C14 C22' -175.1(4) . . . . ?
C7 C13 C14 C22' 6.4(5) . . . . ?
C1 C13 C14 C15 -3.7(3) . . . . ?
C7 C13 C14 C15 177.76(18) . . . . ?
C1 C13 C14 C22 165.78(19) . . . . ?
C7 C13 C14 C22 -12.7(3) . . . . ?
C13 C14 C15 C16 -61.4(3) . . . . ?
C22' C14 C15 C16 111.2(4) . . . . ?
C22 C14 C15 C16 128.6(2) . . . . ?
C13 C14 C15 C20 119.8(3) . . . . ?
C22' C14 C15 C20 -67.6(4) . . . . ?
C22 C14 C15 C20 -50.2(3) . . . . ?
C20 C15 C16 C17 -1.4(3) . . . . ?
C14 C15 C16 C17 179.82(17) . . . . ?
C20 C15 C16 C21 177.5(2) . . . . ?
C14 C15 C16 C21 -1.3(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C21 C16 C17 C18 -178.8(2) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 C15 -1.3(4) . . . . ?
C16 C15 C20 C19 2.0(3) . . . . ?
C14 C15 C20 C19 -179.16(19) . . . . ?
C13 C14 C22 C23 116.0(3) . . . . ?
C22' C14 C22 C23 2.5(15) . . . . ?
C15 C14 C22 C23 -73.6(3) . . . . ?
C13 C14 C22 C27 -68.6(3) . . . . ?
C22' C14 C22 C27 177.9(17) . . . . ?
C15 C14 C22 C27 101.8(2) . . . . ?
C27 C22 C23 C24 0.0 . . . . ?
C14 C22 C23 C24 175.4(3) . . . . ?
C27 C22 C23 C28 177.7(3) . . . . ?
C14 C22 C23 C28 -6.9(3) . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C28 C23 C24 C25 -177.8(3) . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C22 0.0 . . . . ?
C23 C22 C27 C26 0.0 . . . . ?
C14 C22 C27 C26 -175.5(3) . . . . ?
C13 C14 C22' C23' -72.8(6) . . . . ?
C15 C14 C22' C23' 114.9(5) . . . . ?
C22 C14 C22' C23' 4.3(12) . . . . ?
C13 C14 C22' C27' 106.7(5) . . . . ?
C15 C14 C22' C27' -65.7(5) . . . . ?
C22 C14 C22' C27' -176(2) . . . . ?
C27' C22' C23' C24' 0.0 . . . . ?
C14 C22' C23' C24' 179.5(8) . . . . ?
C27' C22' C23' C28' -175.8(8) . . . . ?
C14 C22' C23' C28' 3.7(8) . . . . ?
C22' C23' C24' C25' 0.0 . . . . ?
C28' C23' C24' C25' 175.9(8) . . . . ?
C23' C24' C25' C26' 0.0 . . . . ?
C24' C25' C26' C27' 0.0 . . . . ?
C25' C26' C27' C22' 0.0 . . . . ?
C23' C22' C27' C26' 0.0 . . . . ?
C14 C22' C27' C26' -179.5(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 1006151'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_140411b_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28'
_chemical_formula_sum            'C30 H28'
_chemical_formula_weight         388.52

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           Tetragonal
_symmetry_space_group_name_H-M   P4/n

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

_cell_length_a                   12.9991(19)
_cell_length_b                   12.9991(19)
_cell_length_c                   6.5730(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1110.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5239
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      31.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9871
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11591
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         31.48
_reflns_number_total             1838
_reflns_number_gt                1492
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0679P)²+0.4200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.027(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1838
_refine_ls_number_parameters     132
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1827
_refine_ls_wR_factor_gt          0.1656
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.236
_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 0.23369(15) 0.02693(15) 0.6907(3) 0.0290(7) Uani 0.50 1 d PGD A 1
C2 C 0.27178(17) -0.07284(14) 0.7013(3) 0.0366(8) Uani 0.50 1 d PGD A 1
H2 H 0.2520 -0.1222 0.6022 0.044 Uiso 0.50 1 calc PR A 1
C3 C 0.33874(17) -0.10033(12) 0.8570(4) 0.0402(7) Uani 0.50 1 d PGD A 1
H3 H 0.3648 -0.1685 0.8642 0.048 Uiso 0.50 1 calc PR A 1
C4 C 0.36761(15) -0.02806(16) 1.0020(3) 0.0392(6) Uani 0.50 1 d PGD A 1
H4 H 0.4134 -0.0469 1.1084 0.047 Uiso 0.50 1 calc PR A 1
C5 C 0.32952(15) 0.07171(14) 0.9914(3) 0.0314(7) Uani 0.50 1 d PGD A 1
C6 C 0.26256(16) 0.09921(11) 0.8357(3) 0.0264(8) Uani 0.50 1 d PGD A 1
C7 C 0.1621(2) 0.0530(3) 0.5149(4) 0.0351(11) Uani 0.25 1 d PGD A 1
H7A H 0.1730 0.0040 0.4037 0.053 Uiso 0.25 1 calc PR A 1
H7B H 0.1767 0.1228 0.4667 0.053 Uiso 0.25 1 calc PR A 1
H7C H 0.0905 0.0489 0.5610 0.053 Uiso 0.25 1 calc PR A 1
C8 C 0.3597(4) 0.1438(4) 1.1625(7) 0.0331(10) Uani 0.25 1 d PD A 1
H8A H 0.4304 0.1676 1.1415 0.050 Uiso 0.25 1 calc PR A 1
H8B H 0.3550 0.1074 1.2927 0.050 Uiso 0.25 1 calc PR A 1
H8C H 0.3131 0.2030 1.1639 0.050 Uiso 0.25 1 calc PR A 1
C9 C 0.21988(17) 0.20742(16) 0.8234(3) 0.0246(4) Uani 0.50 1 d PD . .
C10 C 0.10402(13) 0.2117(2) 0.8129(5) 0.0281(7) Uani 0.50 1 d PG A 2
C11 C 0.0557(2) 0.2663(2) 0.6583(4) 0.0491(11) Uani 0.50 1 d PGD A 2
C12 C -0.0508(2) 0.2632(3) 0.6397(4) 0.0670(15) Uani 0.50 1 d PG A 2
H12 H -0.0839 0.3006 0.5340 0.080 Uiso 0.50 1 calc PR A 2
C13 C -0.10892(14) 0.2055(3) 0.7756(5) 0.0623(14) Uani 0.50 1 d PG A 2
H13 H -0.1817 0.2034 0.7629 0.075 Uiso 0.50 1 calc PR A 2
C14 C -0.06054(17) 0.1509(2) 0.9302(5) 0.0572(12) Uani 0.50 1 d PG A 2
H14 H -0.1003 0.1114 1.0231 0.069 Uiso 0.50 1 calc PR A 2
C15 C 0.04592(18) 0.15396(19) 0.9488(4) 0.0496(11) Uani 0.50 1 d PGD A 2
C16 C 0.0947(5) 0.3158(4) 0.4805(8) 0.0331(11) Uani 0.25 1 d PD A 2
H16A H 0.1664 0.2954 0.4592 0.050 Uiso 0.25 1 calc PR A 2
H16B H 0.0908 0.3906 0.4979 0.050 Uiso 0.25 1 calc PR A 2
H16C H 0.0535 0.2954 0.3623 0.050 Uiso 0.25 1 calc PR A 2
C17 C 0.0914(4) 0.1221(4) 1.1667(7) 0.0302(9) Uani 0.25 1 d PD A 2
H17A H 0.0361 0.1229 1.2680 0.045 Uiso 0.25 1 calc PR A 2
H17B H 0.1451 0.1710 1.2065 0.045 Uiso 0.25 1 calc PR A 2
H17C H 0.1209 0.0528 1.1586 0.045 Uiso 0.25 1 calc PR A 2
H1 H 0.1860 0.0436 0.5909 0.036 Uiso 0.25 1 d PR . .
H5 H 0.3499 0.1205 1.0929 0.036 Uiso 0.25 1 d PR . .
H11 H 0.0942 0.3040 0.5654 0.036 Uiso 0.25 1 d PR . .
H15 H 0.0798 0.1168 1.0576 0.036 Uiso 0.25 1 d PR . .


_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 1.3900 . ?
C1 C6 1.3900 . ?
C1 C7 1.5217 . ?
C1 H1 0.9283 . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 C8 1.515(5) . ?
C5 H5 0.9583 . ?
C6 C9 1.514(2) . ?
C6 C9 1.618(3) 3 ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 H1 0.6005 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 H5 0.5628 . ?
C9 C9 0.959(3) 4 ?
C9 C9 0.959(3) 3 ?
C9 C9 1.356(4) 2 ?
C9 C10 1.509(3) . ?
C9 C10 1.613(3) 3 ?
C9 C6 1.618(4) 4 ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C10 C9 1.613(3) 4 ?
C11 C12 1.3900 . ?
C11 C16 1.427(5) . ?
C11 H11 0.9299 . ?
C12 C13 1.3900 . ?
C12 H12 0.9500 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C17 1.604(5) . ?
C15 H15 0.9687 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H11 0.5788 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H15 0.7360 . ?

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 120.0 . . ?
C2 C1 C7 117.6 . . ?
C6 C1 C7 122.4 . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 120.4 . . ?
C7 C1 H1 4.5 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 C8 116.6(2) . . ?
C6 C5 C8 123.3(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 121.0 . . ?
C8 C5 H5 3.8 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C9 120.50(14) . . ?
C1 C6 C9 119.50(14) . . ?
C5 C6 C9 97.76(14) . 3 ?
C1 C6 C9 133.31(14) . 3 ?
C9 C6 C9 35.45(14) . 3 ?
C1 C7 H1 6.9 . . ?
H7A C7 H1 114.5 . . ?
H7B C7 H1 110.8 . . ?
H7C C7 H1 102.9 . . ?
C5 C8 H5 6.5 . . ?
H8A C8 H5 105.4 . . ?
H8B C8 H5 115.9 . . ?
H8C C8 H5 106.9 . . ?
C9 C9 C9 89.997(2) 4 3 ?
C9 C9 C9 44.998(1) 4 2 ?
C9 C9 C9 44.998(1) 3 2 ?
C9 C9 C10 78.2(3) 4 . ?
C9 C9 C10 167.9(3) 3 . ?
C9 C9 C10 123.1(3) 2 . ?
C9 C9 C6 167.8(2) 4 . ?
C9 C9 C6 78.2(2) 3 . ?
C9 C9 C6 123.1(2) 2 . ?
C10 C9 C6 113.7(2) . . ?
C9 C9 C10 156.1(2) 4 3 ?
C9 C9 C10 66.3(2) 3 3 ?
C9 C9 C10 111.2(2) 2 3 ?
C10 C9 C10 125.39(15) . 3 ?
C6 C9 C10 13.18(15) . 3 ?
C9 C9 C6 66.3(2) 4 4 ?
C9 C9 C6 156.1(2) 3 4 ?
C9 C9 C6 111.3(2) 2 4 ?
C10 C9 C6 13.06(19) . 4 ?
C6 C9 C6 125.20(15) . 4 ?
C10 C9 C6 137.5(2) 3 4 ?
C11 C10 C15 120.0 . . ?
C11 C10 C9 120.3(2) . . ?
C15 C10 C9 119.5(2) . . ?
C11 C10 C9 97.27(19) . 4 ?
C15 C10 C9 136.3(2) . 4 ?
C9 C10 C9 35.57(15) . 4 ?
C10 C11 C12 120.0 . . ?
C10 C11 C16 131.9(3) . . ?
C12 C11 C16 107.1(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 119.6 . . ?
C16 C11 H11 14.7 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 C17 116.0(3) . . ?
C10 C15 C17 120.9(3) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 119.8 . . ?
C17 C15 H15 17.2 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C16 H11 24.1 . . ?
H16A C16 H11 94.3 . . ?
H16B C16 H11 98.6 . . ?
H16C C16 H11 133.4 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C17 H15 22.9 . . ?
H17A C17 H15 120.8 . . ?
H17B C17 H15 117.8 . . ?
H17C C17 H15 86.7 . . ?

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 0.0 . . . . ?
C7 C1 C2 C3 179.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 C4 C5 C8 176.4(2) . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C8 C5 C6 C1 -176.1(2) . . . . ?
C4 C5 C6 C9 179.52(18) . . . . ?
C8 C5 C6 C9 3.4(3) . . . . ?
C4 C5 C6 C9 -151.41(15) . . . 3 ?
C8 C5 C6 C9 32.5(2) . . . 3 ?
C2 C1 C6 C5 0.0 . . . . ?
C7 C1 C6 C5 -178.9 . . . . ?
C2 C1 C6 C9 -179.52(18) . . . . ?
C7 C1 C6 C9 1.53(18) . . . . ?
C2 C1 C6 C9 139.3(2) . . . 3 ?
C7 C1 C6 C9 -39.6(2) . . . 3 ?
C5 C6 C9 C9 41.2(6) . . . 4 ?
C1 C6 C9 C9 -139.3(5) . . . 4 ?
C9 C6 C9 C9 -14.9(6) 3 . . 4 ?
C5 C6 C9 C9 56.13(11) . . . 3 ?
C1 C6 C9 C9 -124.35(12) . . . 3 ?
C5 C6 C9 C9 53.49(16) . . . 2 ?
C1 C6 C9 C9 -126.99(10) . . . 2 ?
C9 C6 C9 C9 -2.64(9) 3 . . 2 ?
C5 C6 C9 C10 -126.05(19) . . . . ?
C1 C6 C9 C10 53.5(2) . . . . ?
C9 C6 C9 C10 177.83(16) 3 . . . ?
C5 C6 C9 C10 80.1(7) . . . 3 ?
C1 C6 C9 C10 -100.4(7) . . . 3 ?
C9 C6 C9 C10 24.0(7) 3 . . 3 ?
C5 C6 C9 C6 -118.8(2) . . . 4 ?
C1 C6 C9 C6 60.7(3) . . . 4 ?
C9 C6 C9 C6 -175.0(3) 3 . . 4 ?
C9 C9 C10 C11 55.67(16) 4 . . . ?
C9 C9 C10 C11 42.7(8) 3 . . . ?
C9 C9 C10 C11 53.4(2) 2 . . . ?
C6 C9 C10 C11 -127.07(18) . . . . ?
C10 C9 C10 C11 -120.0(2) 3 . . . ?
C6 C9 C10 C11 79.9(10) 4 . . . ?
C9 C9 C10 C15 -129.48(19) 4 . . . ?
C9 C9 C10 C15 -142.4(6) 3 . . . ?
C9 C9 C10 C15 -131.76(15) 2 . . . ?
C6 C9 C10 C15 47.8(2) . . . . ?
C10 C9 C10 C15 54.9(4) 3 . . . ?
C6 C9 C10 C15 -105.3(10) 4 . . . ?
C9 C9 C10 C9 -12.9(7) 3 . . 4 ?
C9 C9 C10 C9 -2.27(12) 2 . . 4 ?
C6 C9 C10 C9 177.27(12) . . . 4 ?
C10 C9 C10 C9 -175.6(2) 3 . . 4 ?
C6 C9 C10 C9 24.2(9) 4 . . 4 ?
C15 C10 C11 C12 0.0 . . . . ?
C9 C10 C11 C12 174.8(3) . . . . ?
C9 C10 C11 C12 -156.2(2) 4 . . . ?
C15 C10 C11 C16 -167.4(4) . . . . ?
C9 C10 C11 C16 7.4(4) . . . . ?
C9 C10 C11 C16 36.4(4) 4 . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C16 C11 C12 C13 170.2(3) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C10 0.0 . . . . ?
C13 C14 C15 C17 160.2(3) . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
C9 C10 C15 C14 -174.9(3) . . . . ?
C9 C10 C15 C14 144.6(3) 4 . . . ?
C11 C10 C15 C17 -159.2(3) . . . . ?
C9 C10 C15 C17 25.9(3) . . . . ?
C9 C10 C15 C17 -14.6(4) 4 . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        31.48
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 1006152'
