 
data_pyrene3
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C37 H20'
_chemical_formula_sum
 'C37 H20'
_chemical_formula_weight          464.53
 
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            'orthorhombic'
_symmetry_space_group_name_H-M    'P 21 c a'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 'x+1/2, y, -z+1/2'
 'x+1/2, -y, -z'
 'x, -y, z+1/2'
 
_cell_length_a                    8.0620(5)
_cell_length_b                    16.4220(10)
_cell_length_c                    16.7170(10)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2213.2(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     123(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.15
_exptl_crystal_size_min           0.01
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.394
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              968
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.9843
_exptl_absorpt_correction_T_max   0.9992
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       123(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             21081
_diffrn_reflns_av_R_equivalents   0.1247
_diffrn_reflns_av_sigmaI/netI     0.1091
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -21
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.07
_diffrn_reflns_theta_max          27.48
_reflns_number_total              5061
_reflns_number_gt                 2249
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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 > 2σ(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)+(0.0749P)²+0.0000P] 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      SHELXL
_refine_ls_extinction_coef        0.0043(9)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -8(10)
_refine_ls_number_reflns          5061
_refine_ls_number_parameters      335
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1684
_refine_ls_R_factor_gt            0.0639
_refine_ls_wR_factor_ref          0.1715
_refine_ls_wR_factor_gt           0.1308
_refine_ls_goodness_of_fit_ref    0.933
_refine_ls_restrained_S_all       0.933
_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 0.1724(5) 0.1421(3) 0.1357(2) 0.0515(11) Uani 1 1 d . . .
C2 C 0.2403(5) -0.1855(3) 0.1779(2) 0.0522(11) Uani 1 1 d . . .
C3 C -0.0369(5) 0.0388(3) 0.1645(2) 0.0536(11) Uani 1 1 d . . .
H3 H -0.1465 0.0250 0.1804 0.064 Uiso 1 1 calc R . .
C4 C 0.2393(6) -0.0046(3) 0.1202(2) 0.0513(10) Uani 1 1 d . . .
C5 C 0.0115(5) 0.1229(3) 0.1629(2) 0.0517(11) Uani 1 1 d . . .
C6 C 0.4493(5) 0.1000(3) 0.0877(2) 0.0530(11) Uani 1 1 d . . .
C7 C 0.2887(6) 0.0792(3) 0.1152(2) 0.0523(11) Uani 1 1 d . . .
C8 C 0.3561(5) -0.0670(2) 0.1018(2) 0.0509(11) Uani 1 1 d . . .
C9 C 0.2174(5) -0.3799(3) 0.2738(2) 0.0560(11) Uani 1 1 d . . .
C10 C 0.1959(5) -0.2684(3) 0.1782(2) 0.0551(11) Uani 1 1 d . . .
C11 C 0.0709(5) -0.0216(3) 0.1439(2) 0.0534(11) Uani 1 1 d . . .
H11 H 0.0340 -0.0765 0.1451 0.064 Uiso 1 1 calc R . .
C12 C 0.2382(6) -0.3191(3) 0.1168(2) 0.0565(11) Uani 1 1 d . . .
C13 C 0.2238(6) 0.2253(3) 0.1312(2) 0.0570(11) Uani 1 1 d . . .
C14 C 0.4943(6) 0.1850(3) 0.0829(2) 0.0624(13) Uani 1 1 d . . .
H14 H 0.6023 0.1993 0.0650 0.075 Uiso 1 1 calc R . .
C15 C 0.4462(6) -0.5401(3) 0.1771(3) 0.0664(13) Uani 1 1 d . . .
H15 H 0.5023 -0.5891 0.1904 0.080 Uiso 1 1 calc R . .
C16 C 0.1872(5) -0.2984(3) 0.2585(3) 0.0551(11) Uani 1 1 d . . .
C17 C 0.2252(6) -0.2386(3) 0.3138(2) 0.0568(11) Uani 1 1 d . . .
C18 C 0.5131(5) -0.0442(3) 0.0739(2) 0.0540(12) Uani 1 1 d . . .
H18 H 0.5899 -0.0853 0.0589 0.065 Uiso 1 1 calc R . .
C19 C 0.4570(6) -0.5085(3) 0.0961(3) 0.0652(13) Uani 1 1 d . . .
H19 H 0.5220 -0.5365 0.0575 0.078 Uiso 1 1 calc R . .
C20 C 0.3544(6) -0.4995(3) 0.2356(3) 0.0635(12) Uani 1 1 d . . .
C21 C 0.3108(5) -0.1544(3) 0.1086(2) 0.0519(11) Uani 1 1 d . . .
C22 C 0.3736(6) -0.4379(3) 0.0745(3) 0.0655(13) Uani 1 1 d . . .
C23 C 0.3601(6) -0.2105(3) 0.0447(2) 0.0577(11) Uani 1 1 d . . .
H23 H 0.4158 -0.1898 -0.0011 0.069 Uiso 1 1 calc R . .
C24 C 0.3872(7) 0.2447(3) 0.1031(2) 0.0642(13) Uani 1 1 d . . .
H24 H 0.4203 0.3000 0.0986 0.077 Uiso 1 1 calc R . .
C25 C 0.2836(6) -0.2637(3) 0.3886(2) 0.0595(12) Uani 1 1 d . . .
H25 H 0.3023 -0.2250 0.4298 0.071 Uiso 1 1 calc R . .
C26 C -0.0474(7) 0.2653(3) 0.1820(2) 0.0663(13) Uani 1 1 d . . .
H26 H -0.1213 0.3070 0.1988 0.080 Uiso 1 1 calc R . .
C27 C 0.3268(5) -0.2937(3) 0.0497(2) 0.0570(12) Uani 1 1 d . . .
C28 C 0.2355(6) -0.1573(2) 0.2663(2) 0.0572(11) Uani 1 1 d . . .
H28A H 0.1373 -0.1227 0.2767 0.069 Uiso 1 1 calc R . .
H28B H 0.3370 -0.1266 0.2804 0.069 Uiso 1 1 calc R . .
C29 C 0.5599(6) 0.0374(3) 0.0675(2) 0.0585(12) Uani 1 1 d . . .
H29 H 0.6682 0.0507 0.0493 0.070 Uiso 1 1 calc R . .
C30 C 0.2891(6) -0.4067(3) 0.3450(3) 0.0636(12) Uani 1 1 d . . .
C31 C 0.3623(6) -0.4935(3) 0.3278(3) 0.0704(14) Uani 1 1 d . . .
H31A H 0.4780 -0.4980 0.3472 0.084 Uiso 1 1 calc R . .
H31B H 0.2944 -0.5365 0.3533 0.084 Uiso 1 1 calc R . .
C32 C -0.0974(6) 0.1855(3) 0.1853(2) 0.0605(12) Uani 1 1 d . . .
H32 H -0.2064 0.1726 0.2028 0.073 Uiso 1 1 calc R . .
C33 C 0.2669(6) -0.4042(3) 0.1315(2) 0.0613(12) Uani 1 1 d . . .
C34 C 0.3151(6) -0.3487(3) 0.4026(3) 0.0706(14) Uani 1 1 d . . .
H34 H 0.3554 -0.3652 0.4535 0.085 Uiso 1 1 calc R . .
C35 C 0.2582(6) -0.4344(3) 0.2094(3) 0.0617(12) Uani 1 1 d . . .
C36 C 0.1091(7) 0.2860(3) 0.1547(2) 0.0641(13) Uani 1 1 d . . .
H36 H 0.1400 0.3418 0.1517 0.077 Uiso 1 1 calc R . .
C37 C 0.4044(6) -0.3705(3) 0.0114(2) 0.0641(13) Uani 1 1 d . . .
H37A H 0.5246 -0.3629 0.0018 0.077 Uiso 1 1 calc R . .
H37B H 0.3495 -0.3840 -0.0399 0.077 Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C5 1.410(6) . ?
C1 C13 1.431(6) . ?
C1 C7 1.437(6) . ?
C2 C21 1.388(5) . ?
C2 C10 1.407(6) . ?
C2 C28 1.549(5) . ?
C3 C11 1.364(6) . ?
C3 C5 1.435(6) . ?
C3 H3 0.9500 . ?
C4 C8 1.426(6) . ?
C4 C7 1.435(5) . ?
C4 C11 1.441(6) . ?
C5 C32 1.404(6) . ?
C6 C29 1.402(6) . ?
C6 C7 1.415(6) . ?
C6 C14 1.445(6) . ?
C8 C18 1.400(6) . ?
C8 C21 1.485(5) . ?
C9 C16 1.383(5) . ?
C9 C30 1.396(6) . ?
C9 C35 1.438(6) . ?
C10 C12 1.365(6) . ?
C10 C16 1.432(5) . ?
C11 H11 0.9500 . ?
C12 C27 1.395(6) . ?
C12 C33 1.438(6) . ?
C13 C36 1.416(6) . ?
C13 C24 1.434(6) . ?
C14 C24 1.348(6) . ?
C14 H14 0.9500 . ?
C15 C20 1.397(6) . ?
C15 C19 1.452(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(6) . ?
C17 C25 1.399(6) . ?
C17 C28 1.556(5) . ?
C18 C29 1.396(6) . ?
C18 H18 0.9500 . ?
C19 C22 1.389(6) . ?
C19 H19 0.9500 . ?
C20 C35 1.392(6) . ?
C20 C31 1.546(6) . ?
C21 C23 1.466(6) . ?
C22 C33 1.397(6) . ?
C22 C37 1.549(6) . ?
C23 C27 1.394(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C34 1.438(6) . ?
C25 H25 0.9500 . ?
C26 C32 1.372(6) . ?
C26 C36 1.384(7) . ?
C26 H26 0.9500 . ?
C27 C37 1.547(6) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29 0.9500 . ?
C30 C34 1.370(6) . ?
C30 C31 1.570(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32 0.9500 . ?
C33 C35 1.395(6) . ?
C34 H34 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
 
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
C5 C1 C13 119.8(4) . . ?
C5 C1 C7 121.2(4) . . ?
C13 C1 C7 119.0(4) . . ?
C21 C2 C10 117.6(4) . . ?
C21 C2 C28 134.1(4) . . ?
C10 C2 C28 106.2(3) . . ?
C11 C3 C5 121.5(4) . . ?
C11 C3 H3 119.3 . . ?
C5 C3 H3 119.3 . . ?
C8 C4 C7 119.6(4) . . ?
C8 C4 C11 122.8(4) . . ?
C7 C4 C11 117.6(4) . . ?
C32 C5 C1 119.9(4) . . ?
C32 C5 C3 122.0(4) . . ?
C1 C5 C3 118.1(4) . . ?
C29 C6 C7 118.9(4) . . ?
C29 C6 C14 122.4(4) . . ?
C7 C6 C14 118.7(4) . . ?
C6 C7 C4 120.3(4) . . ?
C6 C7 C1 120.1(4) . . ?
C4 C7 C1 119.6(4) . . ?
C18 C8 C4 118.4(4) . . ?
C18 C8 C21 120.5(4) . . ?
C4 C8 C21 121.1(4) . . ?
C16 C9 C30 122.4(4) . . ?
C16 C9 C35 120.2(4) . . ?
C30 C9 C35 110.3(4) . . ?
C12 C10 C2 121.6(4) . . ?
C12 C10 C16 120.4(4) . . ?
C2 C10 C16 110.5(3) . . ?
C3 C11 C4 121.9(4) . . ?
C3 C11 H11 119.0 . . ?
C4 C11 H11 119.0 . . ?
C10 C12 C27 123.3(4) . . ?
C10 C12 C33 120.4(4) . . ?
C27 C12 C33 110.2(4) . . ?
C36 C13 C1 117.9(4) . . ?
C36 C13 C24 122.4(4) . . ?
C1 C13 C24 119.7(4) . . ?
C24 C14 C6 121.8(4) . . ?
C24 C14 H14 119.1 . . ?
C6 C14 H14 119.1 . . ?
C20 C15 C19 121.0(5) . . ?
C20 C15 H15 119.5 . . ?
C19 C15 H15 119.5 . . ?
C9 C16 C17 121.6(4) . . ?
C9 C16 C10 119.9(4) . . ?
C17 C16 C10 111.8(4) . . ?
C16 C17 C25 117.6(4) . . ?
C16 C17 C28 106.2(3) . . ?
C25 C17 C28 133.7(4) . . ?
C29 C18 C8 121.8(4) . . ?
C29 C18 H18 119.1 . . ?
C8 C18 H18 119.1 . . ?
C22 C19 C15 120.8(5) . . ?
C22 C19 H19 119.6 . . ?
C15 C19 H19 119.6 . . ?
C35 C20 C15 116.2(4) . . ?
C35 C20 C31 106.8(4) . . ?
C15 C20 C31 135.0(5) . . ?
C2 C21 C23 119.2(4) . . ?
C2 C21 C8 121.3(4) . . ?
C23 C21 C8 119.0(3) . . ?
C19 C22 C33 116.8(4) . . ?
C19 C22 C37 134.1(5) . . ?
C33 C22 C37 106.3(4) . . ?
C27 C23 C21 121.3(4) . . ?
C27 C23 H23 119.3 . . ?
C21 C23 H23 119.3 . . ?
C14 C24 C13 120.6(5) . . ?
C14 C24 H24 119.7 . . ?
C13 C24 H24 119.7 . . ?
C17 C25 C34 119.4(4) . . ?
C17 C25 H25 120.3 . . ?
C34 C25 H25 120.3 . . ?
C32 C26 C36 121.0(5) . . ?
C32 C26 H26 119.5 . . ?
C36 C26 H26 119.5 . . ?
C23 C27 C12 116.1(4) . . ?
C23 C27 C37 134.1(4) . . ?
C12 C27 C37 107.2(4) . . ?
C2 C28 C17 103.4(3) . . ?
C2 C28 H28A 111.1 . . ?
C17 C28 H28A 111.1 . . ?
C2 C28 H28B 111.1 . . ?
C17 C28 H28B 111.1 . . ?
H28A C28 H28B 109.0 . . ?
C18 C29 C6 120.9(4) . . ?
C18 C29 H29 119.6 . . ?
C6 C29 H29 119.6 . . ?
C34 C30 C9 116.3(4) . . ?
C34 C30 C31 134.6(4) . . ?
C9 C30 C31 106.6(4) . . ?
C20 C31 C30 102.9(4) . . ?
C20 C31 H31A 111.2 . . ?
C30 C31 H31A 111.2 . . ?
C20 C31 H31B 111.2 . . ?
C30 C31 H31B 111.2 . . ?
H31A C31 H31B 109.1 . . ?
C26 C32 C5 120.3(5) . . ?
C26 C32 H32 119.8 . . ?
C5 C32 H32 119.8 . . ?
C35 C33 C22 121.8(4) . . ?
C35 C33 C12 119.7(4) . . ?
C22 C33 C12 111.6(4) . . ?
C30 C34 C25 122.2(4) . . ?
C30 C34 H34 118.9 . . ?
C25 C34 H34 118.9 . . ?
C20 C35 C33 122.6(5) . . ?
C20 C35 C9 111.7(4) . . ?
C33 C35 C9 119.3(4) . . ?
C26 C36 C13 121.0(5) . . ?
C26 C36 H36 119.5 . . ?
C13 C36 H36 119.5 . . ?
C27 C37 C22 103.6(3) . . ?
C27 C37 H37A 111.0 . . ?
C22 C37 H37A 111.0 . . ?
C27 C37 H37B 111.0 . . ?
C22 C37 H37B 111.0 . . ?
H37A C37 H37B 109.0 . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.171
_refine_diff_density_min   -0.202
_refine_diff_density_rms    0.045


