#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/59/1505969.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_1505969
loop_
_publ_author_name
'Kim, Daehwan'
'Petersen, Jeffrey L.'
'Wang, Kung K.'
_publ_section_title
;
 Synthesis of bowl-shaped polycyclic aromatic hydrocarbons via
 palladium-catalyzed intramolecular arylation reactions.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2313
_journal_page_last               2316
_journal_paper_doi               10.1021/ol0605676
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C27 H18'
_chemical_formula_weight         342.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.081(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9891(11)
_cell_length_b                   9.0635(11)
_cell_length_c                   19.991(2)
_cell_measurement_temperature    295(2)
_cell_volume                     1762.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0926
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11850
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0596
_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)+(0.0730P)²+0.2100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1701
_reflns_number_gt                2652
_reflns_number_total             3994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0605676si20060308_022455.cif
_cod_data_source_block           dwk3ccd
_cod_original_cell_volume        1762.9(4)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1505969
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'
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 0.1226(2) 0.1711(2) -0.07764(11) 0.0494(5) Uani 1 1 d .
C2 C 0.09491(17) 0.2495(2) -0.01448(9) 0.0400(4) Uani 1 1 d .
C3 C -0.02050(16) 0.31376(19) 0.00017(9) 0.0377(4) Uani 1 1 d .
C4 C -0.17277(17) 0.3357(2) -0.03578(10) 0.0441(4) Uani 1 1 d .
H4A H -0.1853 0.4251 -0.0632 0.053 Uiso 1 1 calc R
H4B H -0.2071 0.2524 -0.0651 0.053 Uiso 1 1 calc R
C5 C -0.24531(17) 0.3471(2) 0.02378(10) 0.0429(4) Uani 1 1 d .
C6 C -0.38084(18) 0.3442(2) 0.02853(12) 0.0541(5) Uani 1 1 d .
H6 H -0.4517 0.3483 -0.0107 0.065 Uiso 1 1 calc R
C7 C -0.40878(19) 0.3350(3) 0.09357(13) 0.0606(6) Uani 1 1 d .
H7 H -0.5000 0.3396 0.0970 0.073 Uiso 1 1 calc R
C8 C -0.3086(2) 0.3194(2) 0.15333(12) 0.0569(6) Uani 1 1 d .
H8 H -0.3338 0.3077 0.1951 0.068 Uiso 1 1 calc R
C9 C -0.16936(18) 0.3212(2) 0.15141(10) 0.0441(5) Uani 1 1 d .
C10 C -0.04989(19) 0.2746(2) 0.20577(10) 0.0464(5) Uani 1 1 d .
C11 C -0.0518(2) 0.2014(3) 0.26768(11) 0.0609(6) Uani 1 1 d .
H11 H -0.1306 0.2034 0.2851 0.073 Uiso 1 1 calc R
C12 C 0.0636(3) 0.1265(3) 0.30251(12) 0.0713(7) Uani 1 1 d .
H12 H 0.0610 0.0839 0.3445 0.086 Uiso 1 1 calc R
C13 C 0.1827(2) 0.1108(3) 0.27891(11) 0.0652(6) Uani 1 1 d .
H13 H 0.2552 0.0538 0.3029 0.078 Uiso 1 1 calc R
C14 C 0.19156(19) 0.1813(2) 0.21907(10) 0.0502(5) Uani 1 1 d .
C15 C 0.27579(18) 0.1605(2) 0.16590(11) 0.0506(5) Uani 1 1 d .
C16 C 0.36097(18) 0.0509(3) 0.15070(13) 0.0623(6) Uani 1 1 d .
H16 H 0.4116 -0.0071 0.1858 0.075 Uiso 1 1 calc R
C17 C 0.37148(18) 0.0267(3) 0.08230(14) 0.0638(6) Uani 1 1 d .
H17 H 0.4331 -0.0439 0.0739 0.077 Uiso 1 1 calc R
C18 C 0.29365(18) 0.1039(2) 0.02729(13) 0.0555(6) Uani 1 1 d .
C19 C 0.2577(2) 0.0815(3) -0.04953(14) 0.0757(8) Uani 1 1 d .
H19A H 0.2432 -0.0224 -0.0605 0.091 Uiso 1 1 calc R
H19B H 0.3313 0.1173 -0.0697 0.091 Uiso 1 1 calc R
C20 C -0.14663(16) 0.34609(19) 0.08542(9) 0.0382(4) Uani 1 1 d .
C21 C 0.07797(18) 0.2718(2) 0.18838(9) 0.0430(4) Uani 1 1 d .
C22 C -0.01559(16) 0.34093(18) 0.07055(9) 0.0356(4) Uani 1 1 d .
C23 C 0.09402(16) 0.31441(19) 0.12311(9) 0.0378(4) Uani 1 1 d .
C24 C 0.20954(16) 0.24694(19) 0.10946(10) 0.0413(4) Uani 1 1 d .
C25 C 0.20796(16) 0.2154(2) 0.04188(10) 0.0425(4) Uani 1 1 d .
C26 C 0.0079(2) 0.0664(3) -0.10784(14) 0.0755(8) Uani 1 1 d .
H26A H -0.0048 -0.0024 -0.0733 0.113 Uiso 1 1 calc R
H26B H 0.0307 0.0137 -0.1454 0.113 Uiso 1 1 calc R
H26C H -0.0754 0.1211 -0.1241 0.113 Uiso 1 1 calc R
C27 C 0.1424(4) 0.2818(3) -0.13172(15) 0.0966(10) Uani 1 1 d .
H27A H 0.1625 0.2302 -0.1702 0.145 Uiso 1 1 calc R
H27B H 0.2173 0.3465 -0.1125 0.145 Uiso 1 1 calc R
H27C H 0.0599 0.3386 -0.1466 0.145 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C26 C1 C27 109.9(2)
C26 C1 C2 111.16(15)
C27 C1 C2 110.97(17)
C26 C1 C19 109.45(19)
C27 C1 C19 110.92(19)
C2 C1 C19 104.31(17)
C3 C2 C25 118.05(16)
C3 C2 C1 133.43(16)
C25 C2 C1 106.92(15)
C2 C3 C22 116.14(16)
C2 C3 C4 137.62(17)
C22 C3 C4 104.43(14)
C5 C4 C3 103.71(14)
C6 C5 C20 116.64(19)
C6 C5 C4 134.20(18)
C20 C5 C4 108.83(14)
C5 C6 C7 118.22(19)
C8 C7 C6 123.68(17)
C7 C8 C9 120.3(2)
C8 C9 C20 113.57(18)
C8 C9 C10 128.07(19)
C20 C9 C10 117.34(15)
C21 C10 C11 113.91(19)
C21 C10 C9 116.88(17)
C11 C10 C9 127.57(18)
C12 C11 C10 119.9(2)
C11 C12 C13 124.2(2)
C14 C13 C12 118.6(2)
C13 C14 C21 116.15(19)
C13 C14 C15 135.2(2)
C21 C14 C15 106.61(17)
C16 C15 C24 115.0(2)
C16 C15 C14 135.4(2)
C24 C15 C14 104.99(16)
C15 C16 C17 120.5(2)
C18 C17 C16 122.6(2)
C17 C18 C25 117.4(2)
C17 C18 C19 134.5(2)
C25 C18 C19 107.12(19)
C18 C19 C1 106.37(16)
C5 C20 C9 126.77(16)
C5 C20 C22 108.62(16)
C9 C20 C22 123.24(16)
C10 C21 C23 121.95(17)
C10 C21 C14 126.01(18)
C23 C21 C14 108.17(16)
C23 C22 C20 117.96(16)
C23 C22 C3 125.33(15)
C20 C22 C3 112.97(15)
C22 C23 C24 119.18(17)
C22 C23 C21 121.77(15)
C24 C23 C21 109.68(16)
C25 C24 C23 117.34(16)
C25 C24 C15 124.67(18)
C23 C24 C15 110.39(17)
C24 C25 C18 118.91(19)
C24 C25 C2 123.85(15)
C18 C25 C2 113.68(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C26 1.505(3)
C1 C27 1.520(3)
C1 C2 1.528(3)
C1 C19 1.567(3)
C2 C3 1.381(2)
C2 C25 1.437(3)
C3 C22 1.418(2)
C3 C4 1.541(2)
C4 C5 1.531(3)
C5 C6 1.379(2)
C5 C20 1.393(3)
C6 C7 1.393(3)
C7 C8 1.381(3)
C8 C9 1.400(2)
C9 C20 1.407(3)
C9 C10 1.482(3)
C10 C21 1.398(3)
C10 C11 1.408(3)
C11 C12 1.382(3)
C12 C13 1.383(3)
C13 C14 1.377(3)
C14 C21 1.422(3)
C14 C15 1.509(3)
C15 C16 1.385(3)
C15 C24 1.410(3)
C16 C17 1.412(3)
C17 C18 1.384(3)
C18 C25 1.397(3)
C18 C19 1.510(3)
C20 C22 1.407(2)
C21 C23 1.404(3)
C22 C23 1.356(2)
C23 C24 1.387(2)
C24 C25 1.377(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21156786
