#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/19/1501909.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_1501909
loop_
_publ_author_name
'Wen, Bo'
'Petersen, Jeffrey L.'
'Wang, Kung K.'
_publ_section_title
;
 Synthesis of 1,4-naphthoquinone methides via acid-catalyzed cascade
 cyclizations of benzannulated enediynyl alcohols.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              168
_journal_page_last               171
_journal_paper_doi               10.1021/ol102793a
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C28 H24 O2'
_chemical_formula_weight         392.47
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   11.083(1)
_cell_length_b                   12.964(1)
_cell_length_c                   14.977(1)
_cell_measurement_reflns_used    7932
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.28
_cell_volume                     2151.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14647
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         2.29
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0429
_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)+(0.0492P)²+0.165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                4171
_reflns_number_total             4853
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol102793a_si_002.cif
_cod_data_source_block           bw13ccd
_cod_original_cell_volume        2152.0(3)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1501909
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O1 O 0.27515(17) 0.49772(12) -0.20370(8) 0.0859(4) Uani 1 1 d .
O2 O 0.81910(11) 0.34479(14) 0.26015(13) 0.0957(5) Uani 1 1 d .
C1 C 0.49462(19) 0.60753(13) 0.06212(13) 0.0664(5) Uani 1 1 d .
C2 C 0.40031(16) 0.54335(12) 0.01161(11) 0.0556(4) Uani 1 1 d .
C3 C 0.38335(19) 0.55402(13) -0.07702(12) 0.0650(4) Uani 1 1 d .
H3 H 0.4408 0.5896 -0.1102 0.078 Uiso 1 1 calc R
C4 C 0.27809(19) 0.51175(13) -0.12299(11) 0.0650(5) Uani 1 1 d .
C5 C 0.17113(17) 0.49488(12) -0.06544(11) 0.0591(4) Uani 1 1 d .
C6 C 0.05404(19) 0.49860(15) -0.09910(13) 0.0726(5) Uani 1 1 d .
H6 H 0.0418 0.5077 -0.1600 0.087 Uiso 1 1 calc R
C7 C -0.0432(2) 0.48897(17) -0.04338(16) 0.0798(6) Uani 1 1 d .
H7 H -0.1210 0.4921 -0.0664 0.096 Uiso 1 1 calc R
C8 C -0.02560(18) 0.47456(17) 0.04698(15) 0.0760(5) Uani 1 1 d .
H8 H -0.0919 0.4685 0.0847 0.091 Uiso 1 1 calc R
C9 C 0.09035(16) 0.46895(14) 0.08225(13) 0.0645(4) Uani 1 1 d .
H9 H 0.1013 0.4590 0.1432 0.077 Uiso 1 1 calc R
C10 C 0.18980(15) 0.47821(12) 0.02637(11) 0.0552(4) Uani 1 1 d .
C11 C 0.31666(14) 0.47163(12) 0.05815(10) 0.0514(3) Uani 1 1 d .
C12 C 0.35509(14) 0.39232(11) 0.11054(9) 0.0482(3) Uani 1 1 d .
C13 C 0.47999(13) 0.38058(11) 0.14395(9) 0.0476(3) Uani 1 1 d .
C14 C 0.53039(14) 0.28256(12) 0.15300(10) 0.0510(3) Uani 1 1 d .
H14 H 0.4859 0.2258 0.1342 0.061 Uiso 1 1 calc R
C15 C 0.64394(14) 0.26631(14) 0.18880(11) 0.0571(4) Uani 1 1 d .
H15 H 0.6760 0.2001 0.1924 0.069 Uiso 1 1 calc R
C16 C 0.70888(14) 0.35059(16) 0.21911(13) 0.0642(5) Uani 1 1 d .
C17 C 0.66164(15) 0.44926(15) 0.20961(12) 0.0629(4) Uani 1 1 d .
H17 H 0.7064 0.5055 0.2294 0.075 Uiso 1 1 calc R
C18 C 0.54978(14) 0.46595(12) 0.17151(10) 0.0525(3) Uani 1 1 d .
C19 C 0.50179(17) 0.57303(13) 0.16047(12) 0.0606(4) Uani 1 1 d .
H19A H 0.5533 0.6205 0.1929 0.073 Uiso 1 1 calc R
H19B H 0.4218 0.5766 0.1866 0.073 Uiso 1 1 calc R
C20 C 0.6194(2) 0.6031(2) 0.01816(16) 0.0914(7) Uani 1 1 d .
H20A H 0.6503 0.5340 0.0216 0.137 Uiso 1 1 calc R
H20B H 0.6733 0.6492 0.0486 0.137 Uiso 1 1 calc R
H20C H 0.6129 0.6233 -0.0433 0.137 Uiso 1 1 calc R
C21 C 0.4472(3) 0.71934(15) 0.06127(17) 0.1024(9) Uani 1 1 d .
H21A H 0.4467 0.7448 0.0011 0.154 Uiso 1 1 calc R
H21B H 0.4988 0.7619 0.0972 0.154 Uiso 1 1 calc R
H21C H 0.3668 0.7209 0.0850 0.154 Uiso 1 1 calc R
C22 C 0.27302(14) 0.30426(12) 0.13224(11) 0.0498(3) Uani 1 1 d .
C23 C 0.21507(17) 0.24909(14) 0.06508(13) 0.0660(5) Uani 1 1 d .
H23 H 0.2267 0.2676 0.0057 0.079 Uiso 1 1 calc R
C24 C 0.1404(2) 0.16703(16) 0.08575(18) 0.0823(6) Uani 1 1 d .
H24 H 0.1011 0.1316 0.0403 0.099 Uiso 1 1 calc R
C25 C 0.12376(17) 0.13749(15) 0.17281(19) 0.0813(6) Uani 1 1 d .
H25 H 0.0739 0.0820 0.1863 0.098 Uiso 1 1 calc R
C26 C 0.18118(15) 0.19032(14) 0.23998(15) 0.0667(5) Uani 1 1 d .
H26 H 0.1696 0.1708 0.2991 0.080 Uiso 1 1 calc R
C27 C 0.25644(14) 0.27272(12) 0.21993(11) 0.0533(4) Uani 1 1 d .
H27 H 0.2962 0.3072 0.2658 0.064 Uiso 1 1 calc R
C28 C 0.8719(2) 0.2466(3) 0.2676(3) 0.1587(18) Uani 1 1 d .
H28A H 0.8206 0.2027 0.3026 0.238 Uiso 1 1 calc R
H28B H 0.9491 0.2526 0.2962 0.238 Uiso 1 1 calc R
H28C H 0.8821 0.2174 0.2092 0.238 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
C16 O2 C28 117.19(18)
C20 C1 C2 112.48(16)
C20 C1 C19 110.67(18)
C2 C1 C19 110.40(14)
C20 C1 C21 109.82(19)
C2 C1 C21 105.88(17)
C19 C1 C21 107.36(17)
C3 C2 C11 116.04(15)
C3 C2 C1 121.64(15)
C11 C2 C1 122.18(14)
C2 C3 C4 122.47(17)
O1 C4 C3 122.87(19)
O1 C4 C5 122.12(18)
C3 C4 C5 114.83(15)
C6 C5 C10 119.73(17)
C6 C5 C4 121.98(16)
C10 C5 C4 118.26(15)
C7 C6 C5 120.63(17)
C6 C7 C8 119.96(18)
C7 C8 C9 120.6(2)
C10 C9 C8 119.97(17)
C9 C10 C5 119.03(16)
C9 C10 C11 123.54(14)
C5 C10 C11 117.43(15)
C12 C11 C2 123.19(15)
C12 C11 C10 121.57(14)
C2 C11 C10 113.81(13)
C11 C12 C13 124.41(13)
C11 C12 C22 120.75(14)
C13 C12 C22 114.65(12)
C14 C13 C18 117.80(14)
C14 C13 C12 120.08(13)
C18 C13 C12 122.05(14)
C15 C14 C13 122.72(15)
C14 C15 C16 118.64(16)
O2 C16 C15 124.56(18)
O2 C16 C17 115.64(16)
C15 C16 C17 119.80(15)
C18 C17 C16 121.63(15)
C17 C18 C13 119.31(15)
C17 C18 C19 120.67(14)
C13 C18 C19 120.02(14)
C18 C19 C1 113.16(14)
C27 C22 C23 118.14(15)
C27 C22 C12 120.74(13)
C23 C22 C12 121.07(15)
C24 C23 C22 120.65(19)
C25 C24 C23 120.54(19)
C24 C25 C26 119.66(18)
C25 C26 C27 120.25(19)
C22 C27 C26 120.73(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.223(2)
O2 C16 1.370(2)
O2 C28 1.406(4)
C1 C20 1.533(3)
C1 C2 1.535(2)
C1 C19 1.541(3)
C1 C21 1.542(3)
C2 C3 1.348(2)
C2 C11 1.487(2)
C3 C4 1.461(3)
C4 C5 1.482(3)
C5 C6 1.393(3)
C5 C10 1.407(2)
C6 C7 1.368(3)
C7 C8 1.380(3)
C8 C9 1.391(3)
C9 C10 1.389(2)
C10 C11 1.487(2)
C11 C12 1.362(2)
C12 C13 1.480(2)
C12 C22 1.495(2)
C13 C14 1.395(2)
C13 C18 1.412(2)
C14 C15 1.384(2)
C15 C16 1.385(2)
C16 C17 1.390(3)
C17 C18 1.382(2)
C18 C19 1.496(2)
C22 C27 1.388(2)
C22 C23 1.391(2)
C23 C24 1.383(3)
C24 C25 1.371(4)
C25 C26 1.373(3)
C26 C27 1.388(2)
