#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:34:49 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178876 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/05/4110507.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_4110507
loop_
_publ_author_name
'Noach Treitel'
'Lior Eshdat'
'Tuvia Sheradsky'
'Patrick M. Donovan'
'Rik R. Tykwinski'
'Lawrence T. Scott'
'Henning Hopf'
'Mordecai Rabinovitz'
_publ_contact_author_address
; Department of Chemistry
  University of Alberta
  Edmonton, Alberta T6G 2G2
  Canada
;
_publ_contact_author_email       rik.tykwinski@ualberta.ca
_publ_contact_author_fax         1(780)4928231
_publ_contact_author_name        'Dr. Rik R. Tykwinski'
_publ_contact_author_phone       1(780)4925307
_publ_section_title
;
 Reductive Bergman-Type Cyclizations of Cross-Conjugated Enediynes to
 Fulvene and Fulvalene Anions: The Role of the Substituent
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4703
_journal_page_last               4709
_journal_paper_doi               10.1021/ja0566477
_journal_volume                  128
_journal_year                    2006
_chemical_formula_moiety         'C34 H14 F12'
_chemical_formula_sum            'C34 H14 F12'
_chemical_formula_weight         650.45
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           54
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2a 2ac'
_symmetry_space_group_name_H-M   'P c c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'manual editing of SHELXL template'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.2156(14)
_cell_length_b                   14.5870(9)
_cell_length_c                   8.9384(5)
_cell_measurement_reflns_used    4166
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.808
_cell_measurement_theta_min      2.305
_cell_volume                     2896.6(3)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω 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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14905
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       prism
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0480P)²+1.0069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                1942
_reflns_number_total             2958
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja0566477si20051012_043301.cif
_cod_data_source_block           13
_cod_database_code               4110507
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
F21A F 0.0769(3) -0.4228(4) 0.4729(17) 0.138(3) Uani 0.55 1 d P A 1
F22A F 0.1599(6) -0.4158(6) 0.3737(10) 0.132(4) Uani 0.55 1 d P A 1
F23A F 0.1554(5) -0.4507(3) 0.5955(9) 0.121(2) Uani 0.55 1 d P A 1
F21B F 0.0899(7) -0.4157(6) 0.3839(11) 0.135(5) Uani 0.45 1 d P A 2
F22B F 0.1777(6) -0.4346(7) 0.449(2) 0.157(6) Uani 0.45 1 d P A 2
F23B F 0.1064(7) -0.4469(3) 0.6034(9) 0.121(3) Uani 0.45 1 d P A 2
F24 F 0.20692(6) -0.08243(11) 0.87198(15) 0.0771(5) Uani 1 1 d . . .
F25 F 0.24744(10) -0.21343(12) 0.8662(2) 0.1237(7) Uani 1 1 d . . .
F26 F 0.27608(6) -0.10875(13) 0.71468(18) 0.0932(5) Uani 1 1 d . . .
C1 C 0.07093(8) -0.07614(13) 0.4049(2) 0.0379(4) Uani 1 1 d . . .
C2 C 0.03960(8) -0.02296(12) 0.3387(2) 0.0359(4) Uani 1 1 d . . .
C3 C 0.0000 0.03139(16) 0.2500 0.0342(6) Uani 1 2 d S . .
C10 C 0.0000 0.12512(17) 0.2500 0.0356(6) Uani 1 2 d S . .
C11 C 0.03533(8) 0.18611(13) 0.3486(2) 0.0391(4) Uani 1 1 d . . .
C12 C 0.02181(9) 0.27746(13) 0.3116(2) 0.0468(5) Uani 1 1 d . . .
C13 C 0.04808(11) 0.34929(15) 0.3889(3) 0.0620(6) Uani 1 1 d . . .
H13 H 0.0388 0.4110 0.3640 0.074 Uiso 1 1 calc R . .
C14 C 0.08805(12) 0.32950(16) 0.5032(3) 0.0673(7) Uani 1 1 d . . .
H14 H 0.1067 0.3782 0.5565 0.081 Uiso 1 1 calc R . .
C15 C 0.10116(10) 0.23994(16) 0.5405(2) 0.0571(6) Uani 1 1 d . . .
H15 H 0.1287 0.2279 0.6195 0.069 Uiso 1 1 calc R . .
C16 C 0.07495(9) 0.16711(14) 0.4651(2) 0.0456(5) Uani 1 1 d . . .
H16 H 0.0839 0.1056 0.4923 0.055 Uiso 1 1 calc R . .
C21 C 0.10698(8) -0.14139(12) 0.48488(19) 0.0367(4) Uani 1 1 d . . .
C22 C 0.10020(9) -0.23462(13) 0.4557(2) 0.0435(5) Uani 1 1 d . . .
H22 H 0.0716 -0.2547 0.3838 0.052 Uiso 1 1 calc R . .
C23 C 0.13502(10) -0.29797(13) 0.5313(2) 0.0494(5) Uani 1 1 d . A .
C24 C 0.17607(10) -0.26986(15) 0.6382(2) 0.0506(5) Uani 1 1 d . . .
H24 H 0.1997 -0.3137 0.6905 0.061 Uiso 1 1 calc R . .
C25 C 0.18246(9) -0.17786(14) 0.6683(2) 0.0448(5) Uani 1 1 d . . .
C26 C 0.14875(8) -0.11332(13) 0.5918(2) 0.0410(5) Uani 1 1 d . . .
H26 H 0.1541 -0.0499 0.6122 0.049 Uiso 1 1 calc R . .
C27 C 0.12985(16) -0.39724(17) 0.4945(3) 0.0734(7) Uani 1 1 d . . .
C28 C 0.22796(11) -0.14628(17) 0.7802(3) 0.0618(6) Uani 1 1 d . . .
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_3
C2 C1 C21 178.40(19) .
C1 C2 C3 173.36(19) .
C10 C3 C2 123.81(11) .
C10 C3 C2 123.81(11) 3
C2 C3 C2 112.4(2) 3
C3 C10 C11 127.02(11) .
C3 C10 C11 127.02(11) 3
C11 C10 C11 106.0(2) 3
C16 C11 C12 120.01(17) .
C16 C11 C10 131.47(18) .
C12 C11 C10 108.49(17) .
C13 C12 C11 120.68(19) .
C13 C12 C12 130.79(13) 3
C11 C12 C12 108.53(11) 3
C14 C13 C12 118.8(2) .
C15 C14 C13 120.8(2) .
C14 C15 C16 121.3(2) .
C15 C16 C11 118.5(2) .
C22 C21 C26 119.15(17) .
C22 C21 C1 119.62(17) .
C26 C21 C1 121.23(17) .
C23 C22 C21 120.07(19) .
C22 C23 C24 120.57(19) .
C22 C23 C27 119.9(2) .
C24 C23 C27 119.5(2) .
C25 C24 C23 119.49(18) .
C24 C25 C26 120.74(19) .
C24 C25 C28 120.08(19) .
C26 C25 C28 119.13(19) .
C25 C26 C21 119.95(18) .
F21A C27 F22A 107.1(7) .
F21A C27 F23A 109.5(5) .
F22A C27 F23A 102.9(5) .
F22B C27 F23B 109.4(6) .
F22B C27 F21B 103.4(8) .
F23B C27 F21B 99.9(6) .
F21A C27 C23 113.4(4) .
F22B C27 C23 115.2(6) .
F22A C27 C23 110.3(5) .
F23B C27 C23 113.6(3) .
F23A C27 C23 112.9(3) .
F21B C27 C23 113.9(5) .
F25 C28 F24 106.1(2) .
F25 C28 F26 107.3(2) .
F24 C28 F26 105.4(2) .
F25 C28 C25 112.5(2) .
F24 C28 C25 113.08(19) .
F26 C28 C25 111.97(19) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F21A C27 1.249(6) .
F22A C27 1.299(9) .
F23A C27 1.321(5) .
F21B C27 1.355(9) .
F22B C27 1.262(10) .
F23B C27 1.320(6) .
F24 C28 1.326(3) .
F25 C28 1.318(3) .
F26 C28 1.336(3) .
C1 C2 1.199(2) .
C1 C21 1.435(3) .
C2 C3 1.425(2) .
C3 C10 1.367(3) .
C3 C2 1.425(2) 3
C10 C11 1.478(2) .
C10 C11 1.478(2) 3
C11 C16 1.391(3) .
C11 C12 1.405(3) .
C12 C13 1.384(3) .
C12 C12 1.467(4) 3
C13 C14 1.384(3) .
C14 C15 1.380(3) .
C15 C16 1.387(3) .
C21 C22 1.393(3) .
C21 C26 1.394(2) .
C22 C23 1.381(3) .
C23 C24 1.383(3) .
C23 C27 1.489(3) .
C24 C25 1.376(3) .
C25 C26 1.384(3) .
C25 C28 1.495(3) .
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
C21 C1 C2 C3 -50(8) . .
C1 C2 C3 C10 -169.3(15) . .
C1 C2 C3 C2 10.7(15) . 3
C2 C3 C10 C11 -6.28(12) . .
C2 C3 C10 C11 173.72(12) 3 .
C2 C3 C10 C11 173.72(12) . 3
C2 C3 C10 C11 -6.28(12) 3 3
C3 C10 C11 C16 -2.0(2) . .
C11 C10 C11 C16 178.0(2) 3 .
C3 C10 C11 C12 -179.81(10) . .
C11 C10 C11 C12 0.19(10) 3 .
C16 C11 C12 C13 0.7(3) . .
C10 C11 C12 C13 178.89(17) . .
C16 C11 C12 C12 -178.62(19) . 3
C10 C11 C12 C12 -0.5(2) . 3
C11 C12 C13 C14 0.1(3) . .
C12 C12 C13 C14 179.4(3) 3 .
C12 C13 C14 C15 -0.6(4) . .
C13 C14 C15 C16 0.1(4) . .
C14 C15 C16 C11 0.8(3) . .
C12 C11 C16 C15 -1.2(3) . .
C10 C11 C16 C15 -178.83(17) . .
C2 C1 C21 C22 44(7) . .
C2 C1 C21 C26 -136(7) . .
C26 C21 C22 C23 -0.6(3) . .
C1 C21 C22 C23 179.50(18) . .
C21 C22 C23 C24 1.2(3) . .
C21 C22 C23 C27 -176.9(2) . .
C22 C23 C24 C25 -0.6(3) . .
C27 C23 C24 C25 177.6(2) . .
C23 C24 C25 C26 -0.6(3) . .
C23 C24 C25 C28 -178.13(19) . .
C24 C25 C26 C21 1.2(3) . .
C28 C25 C26 C21 178.70(18) . .
C22 C21 C26 C25 -0.5(3) . .
C1 C21 C26 C25 179.33(17) . .
C22 C23 C27 F21A -40.9(9) . .
C24 C23 C27 F21A 141.0(8) . .
C22 C23 C27 F22B 120.0(11) . .
C24 C23 C27 F22B -58.2(11) . .
C22 C23 C27 F22A 79.2(7) . .
C24 C23 C27 F22A -98.9(7) . .
C22 C23 C27 F23B -112.7(8) . .
C24 C23 C27 F23B 69.1(9) . .
C22 C23 C27 F23A -166.2(7) . .
C24 C23 C27 F23A 15.6(7) . .
C22 C23 C27 F21B 0.7(8) . .
C24 C23 C27 F21B -177.4(8) . .
C24 C25 C28 F25 -15.9(3) . .
C26 C25 C28 F25 166.6(2) . .
C24 C25 C28 F24 -136.0(2) . .
C26 C25 C28 F24 46.4(3) . .
C24 C25 C28 F26 105.1(2) . .
C26 C25 C28 F26 -72.4(3) . .
