#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/39/4103992.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_4103992
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_sum            'C50 H42'
_chemical_formula_weight         642.84
_chemical_name_common            tilley01
_chemical_name_systematic
;
 ZL141a
;
_space_group.centring_type       P
_space_group_IT_number           60
_space_group.IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.051(2)
_cell_length_b                   19.381(2)
_cell_length_c                   9.0189(9)
_cell_measurement_reflns_used    6791
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.80
_cell_measurement_theta_min      3.12
_cell_volume                     3679.6(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  Si(111)
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.77490
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_refln_scan_rate          1
_diffrn_refln_scan_width         0.3
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17238
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_correction_T_min  0.9935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0613P)²+0.8629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1311
_reflns_number_gt                2748
_reflns_number_total             3354
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja809930f_si_003.cif
_cod_data_source_block           ZL141a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_database_code               4103992
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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
C1 C 0.0000 0.23529(13) 0.7500 0.0656(9) Uani 1 2 d S
H1A H 0.0220 0.2521 0.8386 0.098 Uiso 0.25 1 calc PR
H1B H -0.0439 0.2521 0.7501 0.098 Uiso 0.25 1 calc PR
H1C H 0.0219 0.2521 0.6612 0.098 Uiso 0.25 1 calc PR
H1D H -0.0220 0.2521 0.6614 0.098 Uiso 0.25 1 calc PR
H1E H 0.0439 0.2521 0.7499 0.098 Uiso 0.25 1 calc PR
H1F H -0.0219 0.2521 0.8388 0.098 Uiso 0.25 1 calc PR
C2 C 0.0000 0.15782(11) 0.7500 0.0395(6) Uani 1 2 d S
C3 C -0.02825(7) 0.12074(8) 0.63613(19) 0.0343(4) Uani 1 1 d .
H3 H -0.0471 0.1449 0.5557 0.041 Uiso 1 1 calc R
C4 C -0.02955(7) 0.04942(7) 0.63719(17) 0.0287(3) Uani 1 1 d .
H4 H -0.0509 0.0255 0.5600 0.034 Uiso 1 1 calc R
C5 C 0.0000 0.01218(10) 0.7500 0.0246(4) Uani 1 2 d S
C6 C 0.0000 -0.06413(10) 0.7500 0.0263(4) Uani 1 2 d S
C7 C 0.05432(7) -0.10723(7) 0.77903(16) 0.0262(3) Uani 1 1 d .
C8 C 0.11996(7) -0.08578(7) 0.81076(16) 0.0256(3) Uani 1 1 d .
C9 C 0.15283(7) -0.04002(8) 0.72011(18) 0.0325(4) Uani 1 1 d .
H9 H 0.1312 -0.0175 0.6414 0.039 Uiso 1 1 calc R
C10 C 0.21687(8) -0.02697(9) 0.74350(19) 0.0376(4) Uani 1 1 d .
H10 H 0.2384 0.0044 0.6801 0.045 Uiso 1 1 calc R
C11 C 0.25018(7) -0.05871(8) 0.85735(19) 0.0354(4) Uani 1 1 d .
C12 C 0.21678(7) -0.10269(8) 0.95062(18) 0.0329(4) Uani 1 1 d .
H12 H 0.2382 -0.1241 1.0311 0.039 Uiso 1 1 calc R
C13 C 0.15301(7) -0.11599(7) 0.92870(17) 0.0304(3) Uani 1 1 d .
H13 H 0.1313 -0.1461 0.9946 0.037 Uiso 1 1 calc R
C14 C 0.32022(8) -0.04658(11) 0.8791(3) 0.0554(5) Uani 1 1 d .
H14A H 0.3443 -0.0837 0.8311 0.083 Uiso 1 1 calc R
H14B H 0.3299 -0.0460 0.9854 0.083 Uiso 1 1 calc R
H14C H 0.3321 -0.0022 0.8350 0.083 Uiso 1 1 calc R
C15 C 0.03349(7) -0.17674(7) 0.76645(16) 0.0267(3) Uani 1 1 d .
C16 C 0.05494(7) -0.24634(7) 0.77340(17) 0.0287(3) Uani 1 1 d .
C17 C 0.12021(7) -0.27160(7) 0.79793(17) 0.0287(3) Uani 1 1 d .
C18 C 0.17025(7) -0.24498(8) 0.71491(18) 0.0339(4) Uani 1 1 d .
H18 H 0.1621 -0.2099 0.6438 0.041 Uiso 1 1 calc R
C19 C 0.23170(8) -0.26877(8) 0.73434(19) 0.0376(4) Uani 1 1 d .
H19 H 0.2649 -0.2498 0.6759 0.045 Uiso 1 1 calc R
C20 C 0.24573(8) -0.31955(8) 0.83710(19) 0.0387(4) Uani 1 1 d .
C21 C 0.19582(8) -0.34562(8) 0.92130(19) 0.0401(4) Uani 1 1 d .
H21 H 0.2042 -0.3801 0.9935 0.048 Uiso 1 1 calc R
C22 C 0.13435(8) -0.32239(7) 0.90202(19) 0.0359(4) Uani 1 1 d .
H22 H 0.1012 -0.3414 0.9607 0.043 Uiso 1 1 calc R
C23 C 0.31253(8) -0.34564(11) 0.8549(2) 0.0527(5) Uani 1 1 d .
H23A H 0.3244 -0.3728 0.7676 0.079 Uiso 1 1 calc R
H23B H 0.3152 -0.3747 0.9437 0.079 Uiso 1 1 calc R
H23C H 0.3416 -0.3064 0.8651 0.079 Uiso 1 1 calc R
C24 C 0.0000 -0.28914(10) 0.7500 0.0305(5) Uani 1 2 d S
C25 C 0.0000 -0.36521(10) 0.7500 0.0282(5) Uani 1 2 d S
C26 C -0.04155(7) -0.40252(7) 0.83999(17) 0.0307(4) Uani 1 1 d .
H26 H -0.0706 -0.3785 0.9019 0.037 Uiso 1 1 calc R
C27 C -0.04111(7) -0.47388(7) 0.84049(18) 0.0320(4) Uani 1 1 d .
H27 H -0.0694 -0.4980 0.9039 0.038 Uiso 1 1 calc R
C28 C 0.0000 -0.51087(10) 0.7500 0.0306(5) Uani 1 2 d S
C29 C 0.0000 -0.58871(11) 0.7500 0.0402(6) Uani 1 2 d S
H29A H -0.0319 -0.6056 0.8203 0.060 Uiso 0.25 1 calc PR
H29B H 0.0420 -0.6056 0.7794 0.060 Uiso 0.25 1 calc PR
H29C H -0.0101 -0.6056 0.6503 0.060 Uiso 0.25 1 calc PR
H29D H 0.0319 -0.6056 0.6797 0.060 Uiso 0.25 1 calc PR
H29E H -0.0420 -0.6056 0.7206 0.060 Uiso 0.25 1 calc PR
H29F H 0.0101 -0.6056 0.8497 0.060 Uiso 0.25 1 calc PR
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'
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
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C2 C1 H1D 109.5 . .
H1A C1 H1D 141.1 . .
H1B C1 H1D 56.3 . .
H1C C1 H1D 56.3 . .
C2 C1 H1E 109.5 . .
H1A C1 H1E 56.3 . .
H1B C1 H1E 141.1 . .
H1C C1 H1E 56.3 . .
H1D C1 H1E 109.5 . .
C2 C1 H1F 109.5 . .
H1A C1 H1F 56.3 . .
H1B C1 H1F 56.3 . .
H1C C1 H1F 141.1 . .
H1D C1 H1F 109.5 . .
H1E C1 H1F 109.5 . .
C3 C2 C3 117.61(19) . 4_556
C3 C2 C1 121.19(10) . .
C3 C2 C1 121.19(10) 4_556 .
C4 C3 C2 121.41(15) . .
C4 C3 H3 119.3 . .
C2 C3 H3 119.3 . .
C3 C4 C5 120.92(14) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C4 C5 C4 117.62(18) 4_556 .
C4 C5 C6 121.19(9) 4_556 .
C4 C5 C6 121.19(9) . .
C7 C6 C7 109.09(17) 4_556 .
C7 C6 C5 125.45(8) 4_556 .
C7 C6 C5 125.45(8) . .
C15 C7 C6 106.88(12) . .
C15 C7 C8 124.97(13) . .
C6 C7 C8 128.12(13) . .
C9 C8 C13 117.80(13) . .
C9 C8 C7 122.22(13) . .
C13 C8 C7 119.78(13) . .
C10 C9 C8 120.68(14) . .
C10 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
C11 C10 C9 121.52(14) . .
C11 C10 H10 119.2 . .
C9 C10 H10 119.2 . .
C10 C11 C12 117.68(14) . .
C10 C11 C14 121.47(15) . .
C12 C11 C14 120.85(15) . .
C13 C12 C11 121.33(14) . .
C13 C12 H12 119.3 . .
C11 C12 H12 119.3 . .
C12 C13 C8 120.92(14) . .
C12 C13 H13 119.5 . .
C8 C13 H13 119.5 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C7 C15 C16 142.81(14) . .
C7 C15 C15 108.56(8) . 4_556
C16 C15 C15 108.62(8) . 4_556
C15 C16 C24 106.55(13) . .
C15 C16 C17 128.05(13) . .
C24 C16 C17 125.40(13) . .
C18 C17 C22 117.58(14) . .
C18 C17 C16 120.09(13) . .
C22 C17 C16 122.33(14) . .
C19 C18 C17 121.05(15) . .
C19 C18 H18 119.5 . .
C17 C18 H18 119.5 . .
C18 C19 C20 121.41(16) . .
C18 C19 H19 119.3 . .
C20 C19 H19 119.3 . .
C19 C20 C21 117.56(15) . .
C19 C20 C23 120.71(17) . .
C21 C20 C23 121.73(16) . .
C22 C21 C20 121.36(16) . .
C22 C21 H21 119.3 . .
C20 C21 H21 119.3 . .
C21 C22 C17 121.04(15) . .
C21 C22 H22 119.5 . .
C17 C22 H22 119.5 . .
C20 C23 H23A 109.5 . .
C20 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C20 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C16 C24 C16 109.59(17) . 4_556
C16 C24 C25 125.21(9) . .
C16 C24 C25 125.21(9) 4_556 .
C26 C25 C26 117.57(18) . 4_556
C26 C25 C24 121.21(9) . .
C26 C25 C24 121.21(9) 4_556 .
C27 C26 C25 121.06(14) . .
C27 C26 H26 119.5 . .
C25 C26 H26 119.5 . .
C26 C27 C28 121.23(14) . .
C26 C27 H27 119.4 . .
C28 C27 H27 119.4 . .
C27 C28 C27 117.85(18) 4_556 .
C27 C28 C29 121.08(9) 4_556 .
C27 C28 C29 121.08(9) . .
C28 C29 H29A 109.5 . .
C28 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
C28 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C28 C29 H29D 109.5 . .
H29A C29 H29D 141.1 . .
H29B C29 H29D 56.3 . .
H29C C29 H29D 56.3 . .
C28 C29 H29E 109.5 . .
H29A C29 H29E 56.3 . .
H29B C29 H29E 141.1 . .
H29C C29 H29E 56.3 . .
H29D C29 H29E 109.5 . .
C28 C29 H29F 109.5 . .
H29A C29 H29F 56.3 . .
H29B C29 H29F 56.3 . .
H29C C29 H29F 141.1 . .
H29D C29 H29F 109.5 . .
H29E C29 H29F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.502(3) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C1 H1D 0.9800 .
C1 H1E 0.9800 .
C1 H1F 0.9800 .
C2 C3 1.387(2) .
C2 C3 1.387(2) 4_556
C3 C4 1.382(2) .
C3 H3 0.9500 .
C4 C5 1.3940(17) .
C4 H4 0.9500 .
C5 C4 1.3940(17) 4_556
C5 C6 1.479(3) .
C6 C7 1.4401(18) 4_556
C6 C7 1.4401(18) .
C7 C15 1.4212(19) .
C7 C8 1.4711(19) .
C8 C9 1.391(2) .
C8 C13 1.399(2) .
C9 C10 1.388(2) .
C9 H9 0.9500 .
C10 C11 1.387(2) .
C10 H10 0.9500 .
C11 C12 1.389(2) .
C11 C14 1.506(2) .
C12 C13 1.381(2) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.4238(19) .
C15 C15 1.441(3) 4_556
C16 C24 1.4389(18) .
C16 C17 1.475(2) .
C17 C18 1.392(2) .
C17 C22 1.392(2) .
C18 C19 1.384(2) .
C18 H18 0.9500 .
C19 C20 1.384(2) .
C19 H19 0.9500 .
C20 C21 1.391(2) .
C20 C23 1.503(2) .
C21 C22 1.381(2) .
C21 H21 0.9500 .
C22 H22 0.9500 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 C16 1.4389(18) 4_556
C24 C25 1.474(3) .
C25 C26 1.3951(18) .
C25 C26 1.3951(18) 4_556
C26 C27 1.383(2) .
C26 H26 0.9500 .
C27 C28 1.3888(18) .
C27 H27 0.9500 .
C28 C27 1.3888(18) 4_556
C28 C29 1.509(3) .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C29 H29D 0.9800 .
C29 H29E 0.9800 .
C29 H29F 0.9800 .
