  
data_cd21335 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C26 H16' 
_chemical_formula_weight          328.39 
  
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)/n 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
  
_cell_length_a                    5.8492(16) 
_cell_length_b                    13.351(4) 
_cell_length_c                    21.102(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  91.971(5) 
_cell_angle_gamma                 90.00 
_cell_volume                      1646.9(8) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     273(2) 
_cell_measurement_reflns_used     1205 
_cell_measurement_theta_min       4.923 
_cell_measurement_theta_max       44.076 
  
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.212 
_exptl_crystal_size_mid           0.156 
_exptl_crystal_size_min           0.113 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.324 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              688 
_exptl_absorpt_coefficient_mu     0.075 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.5618 
_exptl_absorpt_correction_T_max   0.7456 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       273(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             9322 
_diffrn_reflns_av_R_equivalents   0.0574 
_diffrn_reflns_av_sigmaI/netI     0.0598 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -25 
_diffrn_reflns_limit_l_max        25 
_diffrn_reflns_theta_min          1.81 
_diffrn_reflns_theta_max          25.50 
_reflns_number_total              3057 
_reflns_number_gt                 1938 
_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)+(0.0804P)²+0.1800P] 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      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3057 
_refine_ls_number_parameters      235 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1055 
_refine_ls_R_factor_gt            0.0678 
_refine_ls_wR_factor_ref          0.1823 
_refine_ls_wR_factor_gt           0.1630 
_refine_ls_goodness_of_fit_ref    1.054 
_refine_ls_restrained_S_all       1.054 
_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 0.8540(4) 0.64756(17) 0.18075(13) 0.0456(7) Uani 1 1 d . . . 
C2 C 1.0034(5) 0.6370(2) 0.13030(14) 0.0534(7) Uani 1 1 d . . . 
H2 H 1.1405 0.6724 0.1314 0.064 Uiso 1 1 calc R . . 
C3 C 0.9519(6) 0.5762(2) 0.07982(15) 0.0674(9) Uani 1 1 d . . . 
H3 H 1.0546 0.5700 0.0474 0.081 Uiso 1 1 calc R . . 
C4 C 0.7467(6) 0.5232(2) 0.07656(17) 0.0737(10) Uani 1 1 d . . . 
H4 H 0.7095 0.4841 0.0412 0.088 Uiso 1 1 calc R . . 
C5 C 0.6023(6) 0.5287(2) 0.12481(16) 0.0629(9) Uani 1 1 d . . . 
H5 H 0.4659 0.4928 0.1225 0.075 Uiso 1 1 calc R . . 
C6 C 0.6542(5) 0.58779(19) 0.17873(14) 0.0503(7) Uani 1 1 d . . . 
C7 C 0.5212(5) 0.5823(2) 0.23301(16) 0.0584(8) Uani 1 1 d . . . 
H7 H 0.3808 0.5496 0.2307 0.070 Uiso 1 1 calc R . . 
C8 C 0.5950(5) 0.6240(2) 0.28831(16) 0.0580(8) Uani 1 1 d . . . 
H8 H 0.5125 0.6131 0.3246 0.070 Uiso 1 1 calc R . . 
C9 C 0.7960(5) 0.68422(18) 0.29248(14) 0.0475(7) Uani 1 1 d . . . 
C10 C 0.9077(4) 0.70704(17) 0.23707(13) 0.0432(6) Uani 1 1 d . . . 
C11 C 1.0820(4) 0.78476(17) 0.23921(13) 0.0444(6) Uani 1 1 d . . . 
C12 C 1.1966(5) 0.80563(18) 0.29694(13) 0.0477(7) Uani 1 1 d . . . 
C13 C 1.1020(5) 0.76981(18) 0.35551(14) 0.0536(7) Uani 1 1 d . . . 
C14 C 0.8902(5) 0.71871(19) 0.35342(14) 0.0538(7) Uani 1 1 d . . . 
C15 C 0.7883(7) 0.6959(2) 0.41115(17) 0.0720(10) Uani 1 1 d . . . 
H15 H 0.6472 0.6638 0.4103 0.086 Uiso 1 1 calc R . . 
C16 C 0.8903(9) 0.7196(3) 0.46820(18) 0.0883(12) Uani 1 1 d . . . 
H16 H 0.8182 0.7046 0.5056 0.106 Uiso 1 1 calc R . . 
C17 C 1.1025(9) 0.7664(3) 0.47021(18) 0.0890(12) Uani 1 1 d . . . 
H17 H 1.1753 0.7806 0.5091 0.107 Uiso 1 1 calc R . . 
C18 C 1.2043(7) 0.7916(2) 0.41525(16) 0.0706(10) Uani 1 1 d . . . 
H18 H 1.3451 0.8240 0.4173 0.085 Uiso 1 1 calc R . . 
C19 C 1.3986(5) 0.8651(2) 0.29672(16) 0.0581(8) Uani 1 1 d . . . 
H19 H 1.4821 0.8751 0.3345 0.070 Uiso 1 1 calc R . . 
C20 C 1.4714(5) 0.9071(2) 0.24316(17) 0.0599(9) Uani 1 1 d . . . 
H20 H 1.6136 0.9384 0.2434 0.072 Uiso 1 1 calc R . . 
C21 C 1.3361(5) 0.90468(18) 0.18654(15) 0.0526(7) Uani 1 1 d . . . 
C22 C 1.1340(5) 0.84567(18) 0.18487(13) 0.0475(7) Uani 1 1 d . . . 
C23 C 0.9819(5) 0.8589(2) 0.13222(14) 0.0547(8) Uani 1 1 d . . . 
H23 H 0.8441 0.8241 0.1308 0.066 Uiso 1 1 calc R . . 
C24 C 1.0308(6) 0.9213(2) 0.08319(15) 0.0683(9) Uani 1 1 d . . . 
H24 H 0.9255 0.9296 0.0496 0.082 Uiso 1 1 calc R . . 
C25 C 1.2400(7) 0.9727(2) 0.08359(17) 0.0735(10) Uani 1 1 d . . . 
H25 H 1.2772 1.0124 0.0492 0.088 Uiso 1 1 calc R . . 
C26 C 1.3868(6) 0.9644(2) 0.13395(17) 0.0671(9) Uani 1 1 d . . . 
H26 H 1.5248 0.9990 0.1339 0.081 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 1.407(4) . ? 
C1 C6 1.415(4) . ? 
C1 C10 1.455(4) . ? 
C2 C3 1.365(4) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.393(4) . ? 
C3 H3 0.9300 . ? 
C4 C5 1.347(4) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.409(4) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.408(4) . ? 
C7 C8 1.350(4) . ? 
C7 H7 0.9300 . ? 
C8 C9 1.425(4) . ? 
C8 H8 0.9300 . ? 
C9 C10 1.393(4) . ? 
C9 C14 1.456(4) . ? 
C10 C11 1.454(3) . ? 
C11 C12 1.398(4) . ? 
C11 C22 1.447(4) . ? 
C12 C19 1.424(4) . ? 
C12 C13 1.452(4) . ? 
C13 C18 1.407(4) . ? 
C13 C14 1.414(4) . ? 
C14 C15 1.408(4) . ? 
C15 C16 1.362(5) . ? 
C15 H15 0.9300 . ? 
C16 C17 1.389(6) . ? 
C16 H16 0.9300 . ? 
C17 C18 1.364(5) . ? 
C17 H17 0.9300 . ? 
C18 H18 0.9300 . ? 
C19 C20 1.344(4) . ? 
C19 H19 0.9300 . ? 
C20 C21 1.411(4) . ? 
C20 H20 0.9300 . ? 
C21 C26 1.406(4) . ? 
C21 C22 1.420(4) . ? 
C22 C23 1.410(4) . ? 
C23 C24 1.366(4) . ? 
C23 H23 0.9300 . ? 
C24 C25 1.403(5) . ? 
C24 H24 0.9300 . ? 
C25 C26 1.348(5) . ? 
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 C6 117.0(3) . . ? 
C2 C1 C10 123.4(2) . . ? 
C6 C1 C10 119.2(3) . . ? 
C3 C2 C1 121.6(3) . . ? 
C3 C2 H2 119.2 . . ? 
C1 C2 H2 119.2 . . ? 
C2 C3 C4 120.5(3) . . ? 
C2 C3 H3 119.7 . . ? 
C4 C3 H3 119.7 . . ? 
C5 C4 C3 119.8(3) . . ? 
C5 C4 H4 120.1 . . ? 
C3 C4 H4 120.1 . . ? 
C4 C5 C6 121.2(3) . . ? 
C4 C5 H5 119.4 . . ? 
C6 C5 H5 119.4 . . ? 
C5 C6 C7 121.2(3) . . ? 
C5 C6 C1 119.7(3) . . ? 
C7 C6 C1 118.9(3) . . ? 
C8 C7 C6 120.8(3) . . ? 
C8 C7 H7 119.6 . . ? 
C6 C7 H7 119.6 . . ? 
C7 C8 C9 121.6(3) . . ? 
C7 C8 H8 119.2 . . ? 
C9 C8 H8 119.2 . . ? 
C10 C9 C8 118.8(3) . . ? 
C10 C9 C14 119.9(3) . . ? 
C8 C9 C14 121.3(3) . . ? 
C9 C10 C1 118.2(2) . . ? 
C9 C10 C11 118.6(2) . . ? 
C1 C10 C11 123.1(2) . . ? 
C12 C11 C22 118.1(2) . . ? 
C12 C11 C10 118.9(2) . . ? 
C22 C11 C10 122.9(2) . . ? 
C11 C12 C19 118.8(3) . . ? 
C11 C12 C13 119.4(3) . . ? 
C19 C12 C13 121.8(3) . . ? 
C18 C13 C14 118.2(3) . . ? 
C18 C13 C12 122.1(3) . . ? 
C14 C13 C12 119.4(3) . . ? 
C15 C14 C13 118.3(3) . . ? 
C15 C14 C9 122.5(3) . . ? 
C13 C14 C9 119.0(3) . . ? 
C16 C15 C14 121.9(4) . . ? 
C16 C15 H15 119.0 . . ? 
C14 C15 H15 119.0 . . ? 
C15 C16 C17 119.7(4) . . ? 
C15 C16 H16 120.2 . . ? 
C17 C16 H16 120.2 . . ? 
C18 C17 C16 120.0(4) . . ? 
C18 C17 H17 120.0 . . ? 
C16 C17 H17 120.0 . . ? 
C17 C18 C13 121.8(4) . . ? 
C17 C18 H18 119.1 . . ? 
C13 C18 H18 119.1 . . ? 
C20 C19 C12 121.5(3) . . ? 
C20 C19 H19 119.3 . . ? 
C12 C19 H19 119.3 . . ? 
C19 C20 C21 121.2(3) . . ? 
C19 C20 H20 119.4 . . ? 
C21 C20 H20 119.4 . . ? 
C26 C21 C20 121.9(3) . . ? 
C26 C21 C22 119.5(3) . . ? 
C20 C21 C22 118.4(3) . . ? 
C23 C22 C21 116.9(3) . . ? 
C23 C22 C11 123.4(2) . . ? 
C21 C22 C11 119.3(3) . . ? 
C24 C23 C22 122.0(3) . . ? 
C24 C23 H23 119.0 . . ? 
C22 C23 H23 119.0 . . ? 
C23 C24 C25 119.9(3) . . ? 
C23 C24 H24 120.0 . . ? 
C25 C24 H24 120.0 . . ? 
C26 C25 C24 119.7(3) . . ? 
C26 C25 H25 120.1 . . ? 
C24 C25 H25 120.1 . . ? 
C25 C26 C21 121.5(3) . . ? 
C25 C26 H26 119.2 . . ? 
C21 C26 H26 119.2 . . ? 
  
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 3.6(4) . . . . ? 
C10 C1 C2 C3 176.4(3) . . . . ? 
C1 C2 C3 C4 0.7(5) . . . . ? 
C2 C3 C4 C5 -2.8(5) . . . . ? 
C3 C4 C5 C6 0.4(5) . . . . ? 
C4 C5 C6 C7 -170.5(3) . . . . ? 
C4 C5 C6 C1 4.1(4) . . . . ? 
C2 C1 C6 C5 -5.9(4) . . . . ? 
C10 C1 C6 C5 -179.0(2) . . . . ? 
C2 C1 C6 C7 168.8(2) . . . . ? 
C10 C1 C6 C7 -4.3(4) . . . . ? 
C5 C6 C7 C8 167.4(3) . . . . ? 
C1 C6 C7 C8 -7.3(4) . . . . ? 
C6 C7 C8 C9 7.0(4) . . . . ? 
C7 C8 C9 C10 5.3(4) . . . . ? 
C7 C8 C9 C14 -172.4(3) . . . . ? 
C8 C9 C10 C1 -16.5(3) . . . . ? 
C14 C9 C10 C1 161.2(2) . . . . ? 
C8 C9 C10 C11 167.2(2) . . . . ? 
C14 C9 C10 C11 -15.1(4) . . . . ? 
C2 C1 C10 C9 -156.5(2) . . . . ? 
C6 C1 C10 C9 16.2(3) . . . . ? 
C2 C1 C10 C11 19.6(4) . . . . ? 
C6 C1 C10 C11 -167.7(2) . . . . ? 
C9 C10 C11 C12 25.3(3) . . . . ? 
C1 C10 C11 C12 -150.8(2) . . . . ? 
C9 C10 C11 C22 -151.2(2) . . . . ? 
C1 C10 C11 C22 32.7(4) . . . . ? 
C22 C11 C12 C19 -16.9(3) . . . . ? 
C10 C11 C12 C19 166.5(2) . . . . ? 
C22 C11 C12 C13 160.7(2) . . . . ? 
C10 C11 C12 C13 -16.0(3) . . . . ? 
C11 C12 C13 C18 -177.5(2) . . . . ? 
C19 C12 C13 C18 -0.1(4) . . . . ? 
C11 C12 C13 C14 -3.1(4) . . . . ? 
C19 C12 C13 C14 174.4(2) . . . . ? 
C18 C13 C14 C15 2.5(4) . . . . ? 
C12 C13 C14 C15 -172.1(2) . . . . ? 
C18 C13 C14 C9 -172.2(2) . . . . ? 
C12 C13 C14 C9 13.1(4) . . . . ? 
C10 C9 C14 C15 -178.4(3) . . . . ? 
C8 C9 C14 C15 -0.8(4) . . . . ? 
C10 C9 C14 C13 -3.8(4) . . . . ? 
C8 C9 C14 C13 173.8(2) . . . . ? 
C13 C14 C15 C16 -1.5(5) . . . . ? 
C9 C14 C15 C16 173.1(3) . . . . ? 
C14 C15 C16 C17 -0.9(5) . . . . ? 
C15 C16 C17 C18 2.3(6) . . . . ? 
C16 C17 C18 C13 -1.2(5) . . . . ? 
C14 C13 C18 C17 -1.2(4) . . . . ? 
C12 C13 C18 C17 173.3(3) . . . . ? 
C11 C12 C19 C20 4.8(4) . . . . ? 
C13 C12 C19 C20 -172.6(2) . . . . ? 
C12 C19 C20 C21 8.1(4) . . . . ? 
C19 C20 C21 C26 167.1(3) . . . . ? 
C19 C20 C21 C22 -8.1(4) . . . . ? 
C26 C21 C22 C23 -6.5(4) . . . . ? 
C20 C21 C22 C23 168.8(2) . . . . ? 
C26 C21 C22 C11 -179.7(2) . . . . ? 
C20 C21 C22 C11 -4.3(4) . . . . ? 
C12 C11 C22 C23 -156.0(3) . . . . ? 
C10 C11 C22 C23 20.5(4) . . . . ? 
C12 C11 C22 C21 16.7(3) . . . . ? 
C10 C11 C22 C21 -166.8(2) . . . . ? 
C21 C22 C23 C24 3.5(4) . . . . ? 
C11 C22 C23 C24 176.3(3) . . . . ? 
C22 C23 C24 C25 1.5(4) . . . . ? 
C23 C24 C25 C26 -3.5(5) . . . . ? 
C24 C25 C26 C21 0.3(5) . . . . ? 
C20 C21 C26 C25 -170.3(3) . . . . ? 
C22 C21 C26 C25 4.8(4) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              25.50 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.172 
_refine_diff_density_min   -0.179 
_refine_diff_density_rms    0.050 
