#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:30:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178785 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/39/4103991.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4103991
loop_
_publ_author_name
'Zerubba U. Levi'
'T. Don Tilley'
_publ_section_title
;
 Versatile Synthesis of Pentalene Derivatives via the Pd-Catalyzed
 Homocoupling of Haloenynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2796
_journal_page_last               2797
_journal_paper_doi               10.1021/ja809930f
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C46 H24 F6'
_chemical_formula_sum            'C46 H24 F6'
_chemical_formula_weight         690.67
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.142(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.626(2)
_cell_length_b                   5.4881(7)
_cell_length_c                   19.506(3)
_cell_measurement_reflns_used    9584
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      22.7
_cell_measurement_theta_min      2.59
_cell_volume                     1663.2(4)
_computing_cell_refinement       'Bruker 2004'
_computing_data_collection       'Bruker 2004'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXP
_computing_publication_material  SHELX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      149(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'ccd area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_sigmaI/netI    0.1209
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6930
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2004'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Thin rectangular plate'
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.692
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.692
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0142P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0517
_refine_ls_wR_factor_ref         0.0559
_reflns_number_gt                1206
_reflns_number_total             2381
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja809930f_si_002.cif
_cod_data_source_block           isomerm
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4103991
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'
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
F1 F 0.19052(10) 0.7800(3) 0.16287(8) 0.0757(5) Uani 1 1 d .
F2 F 0.24133(10) 0.4497(3) 0.12931(9) 0.0870(6) Uani 1 1 d .
C3 C 0.43042(15) 1.1790(4) -0.05614(11) 0.0274(6) Uani 1 1 d .
F3 F 0.13026(10) 0.6038(3) 0.07542(8) 0.0848(6) Uani 1 1 d .
C5 C 0.39990(14) 0.8985(4) 0.03002(11) 0.0265(6) Uani 1 1 d .
C6 C 0.35048(15) 0.7648(4) 0.07095(12) 0.0316(7) Uani 1 1 d .
H6A H 0.3765 0.6515 0.1036 0.038 Uiso 1 1 calc R
C7 C 0.36186(15) 1.0686(4) -0.01932(11) 0.0268(6) Uani 1 1 d .
C8 C 0.22429(16) 0.9718(4) 0.01827(12) 0.0340(7) Uani 1 1 d .
H8A H 0.1638 0.9962 0.0152 0.041 Uiso 1 1 calc R
C9 C 0.26160(16) 0.7993(4) 0.06333(12) 0.0295(6) Uani 1 1 d .
C10 C 0.18527(16) 1.4565(5) -0.09240(12) 0.0345(7) Uani 1 1 d .
C11 C 0.22906(15) 1.3027(4) -0.06380(12) 0.0331(7) Uani 1 1 d .
C12 C 0.27368(16) 1.1133(4) -0.02351(12) 0.0303(7) Uani 1 1 d .
C13 C 0.13135(15) 1.6436(4) -0.12522(12) 0.0312(7) Uani 1 1 d .
C14 C 0.36047(14) 1.2884(4) -0.17331(12) 0.0325(7) Uani 1 1 d .
H14A H 0.3257 1.1467 -0.1726 0.039 Uiso 1 1 calc R
C15 C 0.50656(15) 1.0883(4) -0.02632(11) 0.0274(6) Uani 1 1 d .
C16 C 0.16105(16) 1.8018(4) -0.17280(12) 0.0382(7) Uani 1 1 d .
H16A H 0.2179 1.7843 -0.1852 0.046 Uiso 1 1 calc R
C17 C 0.20731(17) 0.6596(5) 0.10654(14) 0.0415(7) Uani 1 1 d .
C18 C 0.41817(14) 1.3454(4) -0.11592(12) 0.0264(6) Uani 1 1 d .
C19 C 0.35340(16) 1.4356(5) -0.23104(13) 0.0421(8) Uani 1 1 d .
H19A H 0.3145 1.3941 -0.2701 0.051 Uiso 1 1 calc R
C20 C 0.46766(14) 1.5544(4) -0.11813(12) 0.0317(7) Uani 1 1 d .
H20A H 0.5074 1.5959 -0.0796 0.038 Uiso 1 1 calc R
C21 C 0.40307(17) 1.6434(5) -0.23178(14) 0.0456(8) Uani 1 1 d .
H21A H 0.3978 1.7456 -0.2713 0.055 Uiso 1 1 calc R
C22 C -0.00486(16) 1.8525(5) -0.13824(14) 0.0512(8) Uani 1 1 d .
H22A H -0.0620 1.8700 -0.1264 0.061 Uiso 1 1 calc R
C23 C 0.04725(16) 1.6698(4) -0.10845(13) 0.0438(8) Uani 1 1 d .
H23A H 0.0258 1.5615 -0.0764 0.053 Uiso 1 1 calc R
C24 C 0.02574(18) 2.0098(5) -0.18510(14) 0.0466(8) Uani 1 1 d .
H24A H -0.0102 2.1355 -0.2055 0.056 Uiso 1 1 calc R
C25 C 0.10868(17) 1.9841(4) -0.20226(13) 0.0446(8) Uani 1 1 d .
H25A H 0.1298 2.0926 -0.2345 0.054 Uiso 1 1 calc R
C26 C 0.46008(16) 1.7035(4) -0.17569(13) 0.0408(7) Uani 1 1 d .
H26A H 0.4941 1.8468 -0.1764 0.049 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C15 C3 C18 126.6(2) . .
C15 C3 C7 106.71(19) . .
C18 C3 C7 126.6(2) . .
C6 C5 C7 121.4(2) . .
C6 C5 C15 132.4(2) . 3_675
C7 C5 C15 106.2(2) . 3_675
C5 C6 C9 118.6(2) . .
C5 C6 H6A 120.7 . .
C9 C6 H6A 120.7 . .
C12 C7 C5 119.6(2) . .
C12 C7 C3 131.4(2) . .
C5 C7 C3 108.9(2) . .
C9 C8 C12 121.7(2) . .
C9 C8 H8A 119.2 . .
C12 C8 H8A 119.2 . .
C8 C9 C6 120.7(2) . .
C8 C9 C17 119.5(2) . .
C6 C9 C17 119.8(2) . .
C11 C10 C13 178.4(3) . .
C10 C11 C12 172.8(3) . .
C7 C12 C8 117.8(2) . .
C7 C12 C11 125.3(2) . .
C8 C12 C11 116.7(2) . .
C16 C13 C23 118.9(2) . .
C16 C13 C10 121.6(2) . .
C23 C13 C10 119.5(2) . .
C19 C14 C18 120.8(2) . .
C19 C14 H14A 119.6 . .
C18 C14 H14A 119.6 . .
C3 C15 C15 111.4(3) . 3_675
C3 C15 C5 142.0(2) . 3_675
C15 C15 C5 106.6(2) 3_675 3_675
C25 C16 C13 120.5(2) . .
C25 C16 H16A 119.8 . .
C13 C16 H16A 119.8 . .
F3 C17 F2 105.4(2) . .
F3 C17 F1 104.1(2) . .
F2 C17 F1 105.2(2) . .
F3 C17 C9 114.1(2) . .
F2 C17 C9 114.2(2) . .
F1 C17 C9 112.9(2) . .
C20 C18 C14 118.4(2) . .
C20 C18 C3 120.7(2) . .
C14 C18 C3 120.8(2) . .
C21 C19 C14 119.7(2) . .
C21 C19 H19A 120.1 . .
C14 C19 H19A 120.1 . .
C26 C20 C18 121.0(2) . .
C26 C20 H20A 119.5 . .
C18 C20 H20A 119.5 . .
C26 C21 C19 120.5(2) . .
C26 C21 H21A 119.8 . .
C19 C21 H21A 119.8 . .
C24 C22 C23 120.2(3) . .
C24 C22 H22A 119.9 . .
C23 C22 H22A 119.9 . .
C22 C23 C13 120.3(3) . .
C22 C23 H23A 119.9 . .
C13 C23 H23A 119.9 . .
C22 C24 C25 119.9(3) . .
C22 C24 H24A 120.1 . .
C25 C24 H24A 120.1 . .
C16 C25 C24 120.2(3) . .
C16 C25 H25A 119.9 . .
C24 C25 H25A 119.9 . .
C21 C26 C20 119.7(2) . .
C21 C26 H26A 120.2 . .
C20 C26 H26A 120.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C17 1.332(3) .
F2 C17 1.325(3) .
C3 C15 1.361(3) .
C3 C18 1.477(3) .
C3 C7 1.482(3) .
F3 C17 1.325(3) .
C5 C6 1.380(3) .
C5 C7 1.424(3) .
C5 C15 1.473(3) 3_675
C6 C9 1.394(3) .
C6 H6A 0.9500 .
C7 C12 1.393(3) .
C8 C9 1.378(3) .
C8 C12 1.413(3) .
C8 H8A 0.9500 .
C9 C17 1.473(3) .
C10 C11 1.187(3) .
C10 C13 1.435(3) .
C11 C12 1.437(3) .
C13 C16 1.386(3) .
C13 C23 1.395(3) .
C14 C19 1.380(3) .
C14 C18 1.396(3) .
C14 H14A 0.9500 .
C15 C15 1.443(4) 3_675
C15 C5 1.473(3) 3_675
C16 C25 1.379(3) .
C16 H16A 0.9500 .
C18 C20 1.387(3) .
C19 C21 1.380(3) .
C19 H19A 0.9500 .
C20 C26 1.384(3) .
C20 H20A 0.9500 .
C21 C26 1.375(3) .
C21 H21A 0.9500 .
C22 C24 1.379(3) .
C22 C23 1.380(3) .
C22 H22A 0.9500 .
C23 H23A 0.9500 .
C24 C25 1.380(3) .
C24 H24A 0.9500 .
C25 H25A 0.9500 .
C26 H26A 0.9500 .
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_4
C7 C5 C6 C9 -0.2(3) . .
C15 C5 C6 C9 178.0(2) 3_675 .
C6 C5 C7 C12 4.2(3) . .
C15 C5 C7 C12 -174.3(2) 3_675 .
C6 C5 C7 C3 -178.7(2) . .
C15 C5 C7 C3 2.7(2) 3_675 .
C15 C3 C7 C12 172.9(2) . .
C18 C3 C7 C12 -10.0(4) . .
C15 C3 C7 C5 -3.7(3) . .
C18 C3 C7 C5 173.5(2) . .
C12 C8 C9 C6 2.3(4) . .
C12 C8 C9 C17 179.0(2) . .
C5 C6 C9 C8 -3.1(3) . .
C5 C6 C9 C17 -179.8(2) . .
C13 C10 C11 C12 28(11) . .
C5 C7 C12 C8 -4.9(3) . .
C3 C7 C12 C8 178.8(2) . .
C5 C7 C12 C11 171.0(2) . .
C3 C7 C12 C11 -5.3(4) . .
C9 C8 C12 C7 1.8(3) . .
C9 C8 C12 C11 -174.5(2) . .
C10 C11 C12 C7 -158.8(19) . .
C10 C11 C12 C8 17(2) . .
C11 C10 C13 C16 141(10) . .
C11 C10 C13 C23 -39(10) . .
C18 C3 C15 C15 -174.0(2) . 3_675
C7 C3 C15 C15 3.2(3) . 3_675
C18 C3 C15 C5 3.6(5) . 3_675
C7 C3 C15 C5 -179.2(3) . 3_675
C23 C13 C16 C25 1.0(4) . .
C10 C13 C16 C25 -178.3(2) . .
C8 C9 C17 F3 36.8(4) . .
C6 C9 C17 F3 -146.5(2) . .
C8 C9 C17 F2 158.0(2) . .
C6 C9 C17 F2 -25.2(4) . .
C8 C9 C17 F1 -81.8(3) . .
C6 C9 C17 F1 94.9(3) . .
C19 C14 C18 C20 0.5(3) . .
C19 C14 C18 C3 -175.5(2) . .
C15 C3 C18 C20 -48.9(3) . .
C7 C3 C18 C20 134.5(2) . .
C15 C3 C18 C14 127.0(3) . .
C7 C3 C18 C14 -49.6(3) . .
C18 C14 C19 C21 -0.9(3) . .
C14 C18 C20 C26 0.1(3) . .
C3 C18 C20 C26 176.2(2) . .
C14 C19 C21 C26 0.6(4) . .
C24 C22 C23 C13 0.3(4) . .
C16 C13 C23 C22 -0.8(4) . .
C10 C13 C23 C22 178.4(2) . .
C23 C22 C24 C25 0.0(4) . .
C13 C16 C25 C24 -0.6(4) . .
C22 C24 C25 C16 0.1(4) . .
C19 C21 C26 C20 0.0(4) . .
C18 C20 C26 C21 -0.4(3) . .
