#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:58:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178414 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/35/4023595.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_4023595
loop_
_publ_author_name
'Mark A. Penick'
'Mathew P. D. Mahindaratne'
'Robert D. Gutierrez'
'Terrill D. Smith'
'Edward R. T. Tiekink'
'George R. Negrete'
_publ_section_title
;
 Tandem Friedel-Crafts Annulation to Novel Perylene Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6378
_journal_page_last               6381
_journal_paper_doi               10.1021/jo800558c
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C36 H52 O2'
_chemical_formula_sum            'C36 H52 O2'
_chemical_formula_weight         516.78
_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                90.869(5)
_cell_angle_beta                 95.234(10)
_cell_angle_gamma                103.709(9)
_cell_formula_units_Z            1
_cell_length_a                   4.608(2)
_cell_length_b                   9.424(4)
_cell_length_c                   17.933(7)
_cell_measurement_reflns_used    2542
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      40.8
_cell_measurement_theta_min      2.5
_cell_volume                     752.8(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  AFC12Κ/SATURN724
_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  0.026
_diffrn_reflns_av_sigmaI/netI    0.034
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3931
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.23
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_all          0.080
_refine_ls_R_factor_gt           0.072
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1166P)²+0.2066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.197
_refine_ls_wR_factor_ref         0.208
_reflns_number_gt                2234
_reflns_number_total             2583
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo800558c-file002.cif
_cod_data_source_block           680051
_cod_database_code               4023595
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2595(3) 0.16617(14) 0.25189(7) 0.0466(4) Uani 1 1 d . . .
C1 C 0.2649(4) 0.08301(19) 0.18799(10) 0.0381(5) Uani 1 1 d . . .
C2 C 0.0785(4) -0.0556(2) 0.17182(10) 0.0413(5) Uani 1 1 d . . .
H2 H -0.0574 -0.0994 0.2056 0.050 Uiso 1 1 calc R . .
C3 C 0.0962(4) -0.12801(19) 0.10518(10) 0.0399(5) Uani 1 1 d . . .
H3 H -0.0301 -0.2215 0.0944 0.048 Uiso 1 1 calc R . .
C4 C 0.2944(4) -0.06741(18) 0.05343(10) 0.0334(4) Uani 1 1 d . . .
C5 C 0.4837(4) 0.07103(18) 0.07117(9) 0.0322(4) Uani 1 1 d . . .
C6 C 0.4688(4) 0.14650(18) 0.13824(9) 0.0355(5) Uani 1 1 d . . .
C7 C 0.6712(5) 0.2976(2) 0.15235(11) 0.0463(5) Uani 1 1 d . . .
H7A H 0.8777 0.2900 0.1659 0.056 Uiso 1 1 calc R . .
H7B H 0.6074 0.3465 0.1943 0.056 Uiso 1 1 calc R . .
C8 C 0.6599(6) 0.3867(2) 0.08334(13) 0.0631(7) Uani 1 1 d . . .
H8A H 0.8247 0.4747 0.0899 0.076 Uiso 1 1 calc R . .
H8B H 0.4714 0.4183 0.0792 0.076 Uiso 1 1 calc R . .
C9 C 0.6822(5) 0.30767(19) 0.01080(11) 0.0459(5) Uani 1 1 d . . .
H9A H 0.8569 0.3624 -0.0125 0.055 Uiso 1 1 calc R . .
H9B H 0.5032 0.3066 -0.0234 0.055 Uiso 1 1 calc R . .
C10 C 0.7111(4) 0.14810(18) 0.02053(9) 0.0332(4) Uani 1 1 d . . .
H10 H 0.9113 0.1545 0.0475 0.040 Uiso 1 1 calc R . .
C11 C 0.0386(4) 0.1092(2) 0.30166(10) 0.0433(5) Uani 1 1 d . . .
H11A H 0.0821 0.0226 0.3255 0.052 Uiso 1 1 calc R . .
H11B H -0.1609 0.0808 0.2739 0.052 Uiso 1 1 calc R . .
C12 C 0.0469(5) 0.2271(2) 0.36042(11) 0.0461(5) Uani 1 1 d . . .
H12A H -0.0293 0.3061 0.3370 0.055 Uiso 1 1 calc R . .
H12B H 0.2553 0.2678 0.3809 0.055 Uiso 1 1 calc R . .
C13 C -0.1398(5) 0.1688(2) 0.42391(10) 0.0450(5) Uani 1 1 d . . .
H13A H -0.0616 0.0904 0.4473 0.054 Uiso 1 1 calc R . .
H13B H -0.3469 0.1264 0.4030 0.054 Uiso 1 1 calc R . .
C14 C -0.1412(5) 0.2847(2) 0.48400(11) 0.0468(5) Uani 1 1 d . . .
H14A H 0.0667 0.3323 0.5023 0.056 Uiso 1 1 calc R . .
H14B H -0.2335 0.3594 0.4614 0.056 Uiso 1 1 calc R . .
C15 C -0.3088(5) 0.2242(2) 0.55016(11) 0.0491(5) Uani 1 1 d . . .
H15A H -0.2215 0.1467 0.5714 0.059 Uiso 1 1 calc R . .
H15B H -0.5184 0.1799 0.5320 0.059 Uiso 1 1 calc R . .
C16 C -0.3016(5) 0.3380(2) 0.61203(12) 0.0510(5) Uani 1 1 d . . .
H16A H -0.0919 0.3853 0.6286 0.061 Uiso 1 1 calc R . .
H16B H -0.3970 0.4133 0.5913 0.061 Uiso 1 1 calc R . .
C17 C -0.4577(6) 0.2763(3) 0.67944(12) 0.0605(6) Uani 1 1 d . . .
H17A H -0.3689 0.1979 0.6989 0.073 Uiso 1 1 calc R . .
H17B H -0.6700 0.2334 0.6634 0.073 Uiso 1 1 calc R . .
C18 C -0.4358(8) 0.3898(3) 0.74209(15) 0.0883(10) Uani 1 1 d . . .
H18A H -0.5343 0.3434 0.7840 0.132 Uiso 1 1 calc R . .
H18B H -0.5329 0.4653 0.7241 0.132 Uiso 1 1 calc R . .
H18C H -0.2263 0.4333 0.7582 0.132 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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C1 O1 C11 117.72(14) . . ?
O1 C1 C6 116.09(16) . . ?
O1 C1 C2 123.65(16) . . ?
C6 C1 C2 120.25(17) . . ?
C3 C2 C1 119.01(17) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 122.49(17) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 117.74(17) . . ?
C3 C4 C10 119.85(15) . 2_655 ?
C5 C4 C10 122.35(16) . 2_655 ?
C4 C5 C6 120.70(16) . . ?
C4 C5 C10 123.08(17) . . ?
C6 C5 C10 116.22(15) . . ?
C1 C6 C5 119.79(16) . . ?
C1 C6 C7 122.34(16) . . ?
C5 C6 C7 117.85(16) . . ?
C6 C7 C8 110.46(16) . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C9 114.75(16) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C10 113.97(15) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C5 C10 C4 114.47(15) . 2_655 ?
C5 C10 C9 109.66(15) . . ?
C4 C10 C9 112.85(14) 2_655 . ?
C5 C10 H10 106.4 . . ?
C4 C10 H10 106.4 2_655 . ?
C9 C10 H10 106.4 . . ?
O1 C11 C12 107.96(15) . . ?
O1 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
O1 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C11 C12 C13 111.89(16) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 113.66(16) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 113.55(17) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 114.08(17) . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C15 114.03(17) . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C18 113.4(2) . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.384(2) . ?
O1 C11 1.429(2) . ?
C1 C6 1.393(3) . ?
C1 C2 1.393(3) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.394(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.401(3) . ?
C4 C10 1.514(2) 2_655 ?
C5 C6 1.404(3) . ?
C5 C10 1.511(2) . ?
C6 C7 1.509(2) . ?
C7 C8 1.510(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.513(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.552(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C4 1.514(2) 2_655 ?
C10 H10 0.9900 . ?
C11 C12 1.511(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C13 1.520(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.524(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.519(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.524(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 C17 1.516(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.519(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O1 C1 C6 175.63(15) . . . . ?
C11 O1 C1 C2 -3.6(3) . . . . ?
O1 C1 C2 C3 178.21(16) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 C10 -176.14(15) . . . 2_655 ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C10 C4 C5 C6 175.87(14) 2_655 . . . ?
C3 C4 C5 C10 179.22(14) . . . . ?
C10 C4 C5 C10 -3.7(3) 2_655 . . . ?
O1 C1 C6 C5 -178.47(13) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
O1 C1 C6 C7 -0.5(3) . . . . ?
C2 C1 C6 C7 178.72(17) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C10 C5 C6 C1 179.96(14) . . . . ?
C4 C5 C6 C7 -177.71(15) . . . . ?
C10 C5 C6 C7 1.9(2) . . . . ?
C1 C6 C7 C8 -131.80(19) . . . . ?
C5 C6 C7 C8 46.2(2) . . . . ?
C6 C7 C8 C9 -45.6(3) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C4 C5 C10 C4 3.4(3) . . . 2_655 ?
C6 C5 C10 C4 -176.15(13) . . . 2_655 ?
C4 C5 C10 C9 131.44(17) . . . . ?
C6 C5 C10 C9 -48.2(2) . . . . ?
C8 C9 C10 C5 46.1(2) . . . . ?
C8 C9 C10 C4 174.99(17) . . . 2_655 ?
C1 O1 C11 C12 -171.91(15) . . . . ?
O1 C11 C12 C13 -169.79(15) . . . . ?
C11 C12 C13 C14 -179.21(16) . . . . ?
C12 C13 C14 C15 -175.75(17) . . . . ?
C13 C14 C15 C16 177.78(17) . . . . ?
C14 C15 C16 C17 -177.56(18) . . . . ?
C15 C16 C17 C18 177.3(2) . . . . ?
