#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/37/1503735.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_1503735
loop_
_publ_author_name
'Toyota, Shinji'
'Onishi, Hiroyuki'
'Kawai, Yoshihiro'
'Morimoto, Takaaki'
'Miyahara, Hiroaki'
'Iwanaga, Tetsuo'
'Wakamatsu, Kan'
_publ_section_title
;
 Stereogenic motif consisting of rigid ring and intraannular chains:
 isolation and structures of stereoisomers of
 9-alkyl-1,8-anthrylene-butadiynylene cyclic dimers.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              321
_journal_page_last               324
_journal_paper_doi               10.1021/ol802488z
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C44 H32'
_chemical_formula_sum            'C44 H32'
_chemical_formula_weight         560.70
_chemical_melting_point_gt       516
_chemical_melting_point_lt       518
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.734(5)
_cell_angle_beta                 100.374(3)
_cell_angle_gamma                111.086(2)
_cell_formula_units_Z            1
_cell_length_a                   9.0642(7)
_cell_length_b                   10.2306(7)
_cell_length_c                   10.1873(7)
_cell_measurement_temperature    173(2)
_cell_volume                     746.24(11)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.828
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_device_type  'Rigaku RAXIS-IV'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4795
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         2819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0617
_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)+(0.1283P)²+0.0795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1673
_refine_ls_wR_factor_ref         0.1703
_reflns_number_gt                2627
_reflns_number_total             2819
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802488z_si_002.cif
_cod_data_source_block           anti-3cBu
_cod_original_cell_volume        746.24(9)
_cod_database_code               1503735
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.62219(15) 0.78711(14) 0.46976(14) 0.0219(3) Uani 1 1 d
C2 C 0.60800(16) 0.88880(15) 0.60136(15) 0.0253(3) Uani 1 1 d
H1 H 0.558(2) 0.962(2) 0.5944(18) 0.031(4) Uiso 1 1 d
C3 C 0.64654(16) 0.88368(15) 0.73807(15) 0.0266(3) Uani 1 1 d
H2 H 0.637(2) 0.960(2) 0.830(2) 0.042(5) Uiso 1 1 d
C4 C 0.69418(16) 0.77177(15) 0.74204(15) 0.0260(3) Uani 1 1 d
H3 H 0.715(2) 0.760(2) 0.837(2) 0.036(4) Uiso 1 1 d
C5 C 0.81400(17) 0.31893(15) 0.49683(17) 0.0268(3) Uani 1 1 d
H4 H 0.838(2) 0.325(2) 0.597(2) 0.042(5) Uiso 1 1 d
C6 C 0.81640(17) 0.20272(16) 0.37015(17) 0.0283(3) Uani 1 1 d
H5 H 0.843(2) 0.122(2) 0.377(2) 0.042(5) Uiso 1 1 d
C7 C 0.76937(16) 0.19568(15) 0.22758(15) 0.0265(3) Uani 1 1 d
H6 H 0.758(2) 0.102(2) 0.131(2) 0.041(5) Uiso 1 1 d
C8 C 0.72976(15) 0.31003(14) 0.21303(14) 0.0217(3) Uani 1 1 d
C9 C 0.71855(14) 0.57623(14) 0.34788(13) 0.0202(3) Uani 1 1 d
C10 C 0.76285(16) 0.55182(15) 0.61754(15) 0.0246(3) Uani 1 1 d
H7 H 0.787(2) 0.548(2) 0.714(2) 0.037(4) Uiso 1 1 d
C11 C 0.68727(15) 0.67540(14) 0.47311(14) 0.0207(3) Uani 1 1 d
C12 C 0.71379(15) 0.66527(14) 0.61034(15) 0.0226(3) Uani 1 1 d
C13 C 0.74131(14) 0.44525(14) 0.34919(14) 0.0205(3) Uani 1 1 d
C14 C 0.77143(15) 0.43861(14) 0.48780(15) 0.0228(3) Uani 1 1 d
C15 C 0.55124(15) 0.78203(14) 0.33033(14) 0.0236(3) Uani 1 1 d
C16 C 0.48308(16) 0.77487(14) 0.21183(14) 0.0252(3) Uani 1 1 d
C17 C 0.65650(15) 0.27703(14) 0.05947(14) 0.0235(3) Uani 1 1 d
C18 C 0.58835(16) 0.24434(14) -0.07132(14) 0.0244(3) Uani 1 1 d
C19 C 0.75174(16) 0.62095(13) 0.22757(13) 0.0220(3) Uani 1 1 d
H8 H 0.790(2) 0.549(2) 0.1653(19) 0.034(4) Uiso 1 1 d
H9 H 0.644(2) 0.5972(19) 0.1500(18) 0.028(4) Uiso 1 1 d
C20 C 0.89036(15) 0.79840(14) 0.29703(14) 0.0231(3) Uani 1 1 d
H10 H 0.8621(19) 0.8801(18) 0.3705(16) 0.024(4) Uiso 1 1 d
H11 H 1.003(2) 0.8136(18) 0.3607(18) 0.026(4) Uiso 1 1 d
C21 C 0.91301(18) 0.84109(17) 0.17280(17) 0.0308(3) Uani 1 1 d
H12 H 1.000(2) 0.962(2) 0.225(2) 0.036(4) Uiso 1 1 d
H13 H 0.798(2) 0.819(2) 0.107(2) 0.035(4) Uiso 1 1 d
C22 C 0.9746(2) 0.7407(2) 0.06286(19) 0.0427(4) Uani 1 1 d
H14 H 1.078(3) 0.750(2) 0.126(2) 0.049(5) Uiso 1 1 d
H15 H 1.002(3) 0.779(3) -0.009(3) 0.067(7) Uiso 1 1 d
H16 H 0.886(3) 0.619(2) -0.005(2) 0.046(5) Uiso 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'
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 C15 116.84(11) .
C2 C1 C11 120.31(12) .
C15 C1 C11 122.36(10) .
C1 C2 C3 121.87(12) .
C1 C2 H1 118.5(9) .
C3 C2 H1 119.4(9) .
C4 C3 C2 119.64(11) .
C4 C3 H2 121.1(11) .
C2 C3 H2 119.3(11) .
C3 C4 C12 120.93(12) .
C3 C4 H3 121.4(10) .
C12 C4 H3 117.7(10) .
C6 C5 C14 121.07(13) .
C6 C5 H4 123.2(11) .
C14 C5 H4 115.7(11) .
C5 C6 C7 119.43(12) .
C5 C6 H5 120.3(11) .
C7 C6 H5 120.1(11) .
C8 C7 C6 121.75(11) .
C8 C7 H6 118.7(10) .
C6 C7 H6 119.5(10) .
C7 C8 C17 117.16(11) .
C7 C8 C13 120.34(12) .
C17 C8 C13 121.96(11) .
C11 C9 C13 118.59(11) .
C11 C9 C19 121.11(10) .
C13 C9 C19 119.76(10) .
C14 C10 C12 121.21(12) .
C14 C10 H7 118.9(11) .
C12 C10 H7 119.8(11) .
C9 C11 C12 119.78(11) .
C9 C11 C1 124.10(11) .
C12 C11 C1 116.09(11) .
C10 C12 C11 119.47(11) .
C10 C12 C4 119.78(12) .
C11 C12 C4 120.74(12) .
C14 C13 C9 119.77(11) .
C14 C13 C8 116.08(11) .
C9 C13 C8 124.11(12) .
C10 C14 C13 119.55(11) .
C10 C14 C5 119.82(13) .
C13 C14 C5 120.62(12) .
C16 C15 C1 176.87(13) .
C15 C16 C18 174.20(12) 2_665
C18 C17 C8 177.36(13) .
C17 C18 C16 173.75(12) 2_665
C9 C19 C20 113.82(10) .
C9 C19 H8 107.2(10) .
C20 C19 H8 108.1(10) .
C9 C19 H9 113.0(9) .
C20 C19 H9 109.8(9) .
H8 C19 H9 104.5(12) .
C21 C20 C19 112.16(10) .
C21 C20 H10 106.8(8) .
C19 C20 H10 112.1(8) .
C21 C20 H11 110.4(9) .
C19 C20 H11 108.1(8) .
H10 C20 H11 107.2(12) .
C20 C21 C22 113.19(12) .
C20 C21 H12 109.1(10) .
C22 C21 H12 108.6(10) .
C20 C21 H13 108.8(10) .
C22 C21 H13 107.3(10) .
H12 C21 H13 109.8(14) .
C21 C22 H14 108.1(12) .
C21 C22 H15 112.0(14) .
H14 C22 H15 109(2) .
C21 C22 H16 112.9(11) .
H14 C22 H16 108.1(16) .
H15 C22 H16 106.9(17) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3899(17) .
C1 C15 1.4218(18) .
C1 C11 1.4712(17) .
C2 C3 1.400(2) .
C2 H1 1.028(17) .
C3 C4 1.3732(19) .
C3 H2 0.993(19) .
C4 C12 1.4378(17) .
C4 H3 1.02(2) .
C5 C6 1.3686(19) .
C5 C14 1.4403(17) .
C5 H4 0.97(2) .
C6 C7 1.403(2) .
C6 H5 0.96(2) .
C7 C8 1.3936(17) .
C7 H6 1.014(18) .
C8 C17 1.4288(17) .
C8 C13 1.4655(16) .
C9 C11 1.4257(16) .
C9 C13 1.4320(16) .
C9 C19 1.5123(17) .
C10 C14 1.4013(17) .
C10 C12 1.4066(18) .
C10 H7 0.99(2) .
C11 C12 1.4271(19) .
C13 C14 1.423(2) .
C15 C16 1.2133(18) .
C16 C18 1.3619(18) 2_665
C17 C18 1.2104(17) .
C18 C16 1.3619(18) 2_665
C19 C20 1.5426(16) .
C19 H8 0.976(17) .
C19 H9 1.019(16) .
C20 C21 1.5194(18) .
C20 H10 1.021(15) .
C20 H11 1.025(15) .
C21 C22 1.527(2) .
C21 H12 1.026(17) .
C21 H13 1.023(17) .
C22 H14 0.98(2) .
C22 H15 0.99(2) .
C22 H16 1.03(2) .
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_4
C15 C1 C2 C3 169.05(12) .
C11 C1 C2 C3 -3.11(19) .
C1 C2 C3 C4 -2.3(2) .
C2 C3 C4 C12 3.28(19) .
C14 C5 C6 C7 -2.8(2) .
C5 C6 C7 C8 3.9(2) .
C6 C7 C8 C17 -169.89(12) .
C6 C7 C8 C13 1.84(19) .
C13 C9 C11 C12 12.85(17) .
C19 C9 C11 C12 -158.71(11) .
C13 C9 C11 C1 -164.96(10) .
C19 C9 C11 C1 23.48(17) .
C2 C1 C11 C9 -174.93(11) .
C15 C1 C11 C9 13.35(18) .
C2 C1 C11 C12 7.18(17) .
C15 C1 C11 C12 -164.53(11) .
C14 C10 C12 C11 -5.77(19) .
C14 C10 C12 C4 175.45(11) .
C9 C11 C12 C10 -2.97(18) .
C1 C11 C12 C10 175.01(10) .
C9 C11 C12 C4 175.79(11) .
C1 C11 C12 C4 -6.22(17) .
C3 C4 C12 C10 179.95(11) .
C3 C4 C12 C11 1.18(19) .
C11 C9 C13 C14 -14.32(17) .
C19 C9 C13 C14 157.36(11) .
C11 C9 C13 C8 163.41(10) .
C19 C9 C13 C8 -24.92(17) .
C7 C8 C13 C14 -8.23(17) .
C17 C8 C13 C14 163.10(11) .
C7 C8 C13 C9 173.97(11) .
C17 C8 C13 C9 -14.71(18) .
C12 C10 C14 C13 4.30(19) .
C12 C10 C14 C5 -176.96(11) .
C9 C13 C14 C10 5.87(18) .
C8 C13 C14 C10 -172.04(10) .
C9 C13 C14 C5 -172.85(10) .
C8 C13 C14 C5 9.24(17) .
C6 C5 C14 C10 177.28(12) .
C6 C5 C14 C13 -4.00(19) .
C2 C1 C15 C16 -62(2) .
C11 C1 C15 C16 110(2) .
C1 C15 C16 C18 -118(2) 2_665
C7 C8 C17 C18 74(3) .
C13 C8 C17 C18 -98(2) .
C8 C17 C18 C16 126(2) 2_665
C11 C9 C19 C20 50.31(15) .
C13 C9 C19 C20 -121.16(11) .
C9 C19 C20 C21 -176.89(10) .
C19 C20 C21 C22 -62.93(15) .
